3,3'-DICHLOROBENZIDINE

Editor's Note: This material is not listed in the Emergency Response Guidebook. Based on the material's physical and chemical properties, toxicity, or chemical group, a guide has been assigned. For additional technical information, contact one of the emergency response telephone numbers listed under Public Safety Measures.

DESIGNATIONS

BEILSTEIN HANDBOOK REFERENCE:4-13-00-00384

MOLECULAR FORMULA

C12-H10-Cl2-N2 C12H12Cl4N2 NH2ClC6H3C6H3ClNH2 C12H10Cl2N2ClH C6H3ClNH2C6H3ClNH2

ERG GUIDE NUMBER

153-SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)

SYNONYM REFERENCE

(ACGIH, 1991; Ashford, 1994; ATSDR, 1998; Budavari, 2000; Hathaway et al, 1996; HSDB , 2001; Lewis, 1998; NIOSH , 2001; RTECS , 2001; Sittig, 1991)

USES/FORMS/SOURCES

USES

3,3'-Dichlorobenzidine is used as a rubber and plastic compounding ingredient, a curing agent for isocyanate-terminated resins in urethane plastics, alone and in mixtures with 4,4'-methylenebis(2-chloroaniline) in curing liquid- castable polyurethane elastomers, and in color tests for the detection of gold (ACGIH, 1991; ATSDR, 1998; Bingham et al, 2001; HSDB , 2001; IARC, 1974; Lewis, 1998; Lewis, 1997; NSC , 2000; Sittig, 1991).
3,3'-Dichlorobenzidine is used in the production of yellow, orange, and red pigments for printing ink, paint, rubber, plastic, textiles, azo dyes, diarylide pigments, as an intermediate for the Benzidine Yellow pigments, and other related industries (ACGIH, 1991; Budavari, 2000; Hathaway et al, 1996; HSDB , 2001; Lewis, 1998; Lewis, 1997; NSC , 2000; OHM/TADS , 2001; Sittig, 1991).

The base, 3,3'-dichlorobenzidine, and salt, 3,3'-dichlorobenzidine dihydrochloride, are used to manufacture yellow pigments 12, 13, 14, 17, 55, 63, 83, 124, 127, 152, 170, and 171; orange pigments 13 and 34; and red pigment 38, which may be used to replace the lead chromate pigments (Ashford, 1994; HSDB , 2001).

3,3'-Dichlorobenzidine is used in the formulation of a raw material, tetraminobiphenyl, which is used to produce polybenzimidazole (PBI). Various types of protective clothing are made from PBI (e.g., firefighters', welders', and crash rescue garments) (NSC , 2000).

FORMS

3,3'-Dichlorobenzidine exists in either the free base form (CAS 91-94-1) or as dihydrochloride salt (CAS 5742-07-4). The salt form is used commercially because of its greater stability (ACGIH, 1991; Ashford, 1994; ATSDR, 1998; Bingham et al, 2001).
Ashford (1994) reports the dihydrochloride CAS number as 5742-07-04, while Lewis (1992) reports it as 612-83-9.

SOURCES

3,3'-Dichlorobenzidene is produced from the alkaline reduction of o-nitrochlorobenzidine in the presence of mineral acids (ATSDR, 1998; IARC, 1974; NSC , 2000).
o-Chloronitrobenzene, by a reductive coupling/acid catalyzed rearrangement, will produce 3,3'-dichlorobenzidine (Ashford, 1994; Budavari, 2000).
This chemical is also produced through chlorination of diacetylbenzidine with hypochlorite, followed by hydrolysis of the diamide to diamine using hydrochloric acid (IARC, 1974).

SYNONYM EXPLANATION

The literature is not always clear whether the base form or the dihydrochloride salt is being considered (Bingham et al, 2001). Literature specific for the base form of 3,3'-dichlorobenzidine (CAS 91-94-1) is used in this document unless otherwise noted.

-CLINICAL EFFECTS

GENERAL CLINICAL EFFECTS

3,3'-Dichlorobenzidine may be toxic by inhalation, ingestion, and skin or eye exposure. It is absorbed through the skin and lungs.

Systemic signs and symptoms of exposure may include dizziness, headache, sneezing, sore throat, upper respiratory tract infection, frequent urination, dysuria, hematuria, anemia, icterus, and gastrointestinal upset. Organ damage may result, affecting the central nervous system, kidney and liver; exposure may be fatal.

Dermal exposure can result in allergic skin reaction, skin sensitization, dermatitis and caustic burns. Exposure to the eyes may produce irritation.

3,3'-Dichlorobenzidine is carcinogenic in experimental animals and is considered a potential occupational carcinogen. OSHA and the EPA's Toxic Release Inventory classify this chemical as a "de minimus" carcinogen. IARC considers 3,3'-Dichlorobenzidine to be in Group 2B (possibly carcinogenic to humans).

POTENTIAL HEALTH HAZARDS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death.
Contact with molten substance may cause severe burns to skin and eyes.
Avoid any skin contact.
Effects of contact or inhalation may be delayed.
Fire may produce irritating, corrosive and/or toxic gases.
Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

-MEDICAL TREATMENT

LIFE SUPPORT

Support respiratory and cardiovascular function.

SUMMARY

FIRST AID - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

Move victim to fresh air.
Call 911 or emergency medical service.
Give artificial respiration if victim is not breathing.
Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult.
Remove and isolate contaminated clothing and shoes.
In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes.
For minor skin contact, avoid spreading material on unaffected skin.
Keep victim warm and quiet.
Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed.
Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.

FIRST AID

FIRST AID

If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Primary eye protection (spectacles or goggles), as defined by the Occupational Safety and Health Administration (OSHA), should be used when working with this chemical. Face shields should only be worn over primary eye protection.

Contact lens use is not recommended when working with this chemical. If contact lenses are worn, then appropriate eye and face protection devices must be used. OSHA emphasizes that dusty and/or chemical environments may represent an additional hazard to contact lens wearers.

DERMAL EXPOSURE - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.
INHALATION EXPOSURE - If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform artificial respiration. Keep the affected person warm and at rest. Get medical attention as soon as possible.
ORAL EXPOSURE - If this chemical has been swallowed, get medical attention immediately.
TARGET ORGANS - Bladder, liver, lung, skin and gastrointestinal tract (National Institute for Occupational Safety and Health, 2007).

GENERAL -

Move victims of inhalation exposure from the toxic environment and administer 100% humidified supplemental oxygen with assisted ventilation as required. Exposed skin and eyes should be copiously flushed with water. Ingestion may result in significant esophageal or gastrointestinal tract irritation or burns, and EMESIS SHOULD NOT BE INDUCED. Cautious gastric lavage followed by administration of activated charcoal may be of benefit if the patient is seen soon after the exposure.

INHALATION EXPOSURE -

INHALATION: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with an inhaled beta2-adrenergic agonist. Consider systemic corticosteroids in patients with significant bronchospasm.

DERMAL EXPOSURE -

DECONTAMINATION: Remove contaminated clothing and jewelry and place them in plastic bags. Wash exposed areas with soap and water for 10 to 15 minutes with gentle sponging to avoid skin breakdown. A physician may need to examine the area if irritation or pain persists (Burgess et al, 1999).
Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines.

EYE EXPOSURE -

DECONTAMINATION: Remove contact lenses and irrigate exposed eyes with copious amounts of room temperature 0.9% saline or water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist after 15 minutes of irrigation, the patient should be seen in a healthcare facility.

INGESTION EXPOSURE -

Because of the potential for gastrointestinal tract irritation, do not induce emesis.
PREHOSPITAL ACTIVATED CHARCOAL ADMINISTRATION

Consider prehospital administration of activated charcoal as an aqueous slurry in patients with a potentially toxic ingestion who are awake and able to protect their airway. Activated charcoal is most effective when administered within one hour of ingestion. Administration in the prehospital setting has the potential to significantly decrease the time from toxin ingestion to activated charcoal administration, although it has not been shown to affect outcome (Alaspaa et al, 2005; Thakore & Murphy, 2002; Spiller & Rogers, 2002).

In patients who are at risk for the abrupt onset of seizures or mental status depression, activated charcoal should not be administered in the prehospital setting, due to the risk of aspiration in the event of spontaneous emesis.
The addition of flavoring agents (cola drinks, chocolate milk, cherry syrup) to activated charcoal improves the palatability for children and may facilitate successful administration (Guenther Skokan et al, 2001; Dagnone et al, 2002).

ACTIVATED CHARCOAL: Administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old.
Observe patients with ingestion carefully for the possible development of esophageal or gastrointestinal tract irritation or burns. If signs or symptoms of esophageal irritation or burns are present, consider endoscopy to determine the extent of injury.

-RANGE OF TOXICITY

MINIMUM LETHAL EXPOSURE

HUMAN DATA

The minimum lethal human dose to this agent has not been delineated.

ANIMAL DATA

An unpublished statement indicates that dermal exposure to 1 g/kg of the base form for 24 hours was lethal to 4 out of 5 rabbits (ACGIH, 1991).

CARCINOGENIC CLASSIFICATION

IARC: Group 2B, possibly carcinogenic in humans
MAK: Group A2, unmistakably carcinogenic in animal experimentation only
ACGIH: A2, suspected human carcinogen
NIOSH: potential occupational carcinogen
The FDA has deemed 3,3'-dichlorobenzidine as a carcinogen, but no regulatory guidelines have been established (ATSDR, 1998).
Although 3,3'-dichlorobenzidine is an animal carcinogen, an IARC working group determined that there are no adequate data available to evaluate the carcinogenic effects of 3,3'-dichlorobenzidine or 3,3'-dichlorobenzidine dihydrochloride in humans (ACGIH, 1991; ATSDR, 1998; Bingham et al, 2001; IARC, 1982; Lewis, 1997).
3,3'-Dichlorobenzidine and its salts are considered anticipated carcinogens and tumorigens, but there has not been a case report of cancer associated with these chemicals (Budavari, 2000; IARC, 1982; Lewis, 2000).

MAXIMUM TOLERATED EXPOSURE

HUMAN DATA

The maximum tolerated human exposure to this agent has not been delineated.
Dermatitis has been reported in dye workers exposed to 3,3'-dichlorobenzidine, but the exposure concentration and duration were not reported (IARC, 1982).

ANIMAL DATA

3,3'-Dichlorobenzidine is a potent carcinogen by oral administration in mice, rats, hamsters, and dogs (ACGIH, 1991; Clayton & Clayton, 1994; IARC, 1982).
Nine of 14 rats lived more than 288 days after ingesting 3,3'-dichlorobenzidine in olive oil at 700 mg/kg for 5 days/week. At autopsy, liver damage and a tumor were the only findings (ACGIH, 1991).
Fifty-one of 111 rats developed various types of tumors when administered 3,3'-dichlorobenzidine by injection or gastric intubation at 20 mg for 6 days/week for 10-20 months (Hathaway et al, 1996).
All female beagle dogs showed evidence of liver damage after oral administration of 3,3'-dichlorobenzidine (100% pure) at 100 mg for 3 times weekly for 6 weeks, and then 5 times weekly for seven years (IARC, 1982).
It is likely that the dihydrochloride salt can be absorbed percutaneously, and has been shown to be a severe eye irritant in rabbits (ACGIH, 1991).

LACK OF EFFECT

Twenty mg of 3,3'-dichlorobenzidine dihydrochloride, as 0.1 mL of 20% corn oil suspension, administered in rabbits' eyes produced pus, corneal opacity, and erythema. No effects were noted when 100 mg of 3,3'-dichlorobenzidine was applied (Hathaway et al, 1996).
Exposure by inhalation to concentrated 3,3'-dichlorobenzidine dust caused some irritation and moderate pulmonary congestion in rats, but was not lethal. No outward adverse effects were seen in 10 male rats exposed to 23,700 mg/m(3) concentrated dust for 2 hours per day for 7 days (ACGIH, 1991; ATSDR, 1998).

Carcinogenicity Ratings for CAS91-94-1 :

ACGIH (American Conference of Governmental Industrial Hygienists, 2010): A3 ; Listed as: 3,3'-Dichlorobenzidine

A3 :Confirmed Animal Carcinogen with Unknown Relevance to Humans: The agent is carcinogenic in experimental animals at a relatively high dose, by route(s) of administration, at site(s), of histologic type(s), or by mechanism(s) that may not be relevant to worker exposure. Available epidemiologic studies do not confirm an increased risk of cancer in exposed humans. Available evidence does not suggest that the agent is likely to cause cancer in humans except under uncommon or unlikely routes or levels of exposure.

ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed ; Listed as: 3,3'-Dichlorobenzidine
EPA (U.S. Environmental Protection Agency, 2011): B2 ; Listed as: 3,3'-Dichlorobenzidine

B2 : Probable human carcinogen - based on sufficient evidence of carcinogenicity in animals.

IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): 2B ; Listed as: 3,3'-Dichlorobenzidine

2B : The agent (mixture) is possibly carcinogenic to humans. The exposure circumstance entails exposures that are possibly carcinogenic to humans. This category is used for agents, mixtures and exposure circumstances for which there is limited evidence of carcinogenicity in humans and less than sufficient evidence of carcinogenicity in experimental animals. It may also be used when there is inadequate evidence of carcinogenicity in humans but there is sufficient evidence of carcinogenicity in experimental animals. In some instances, an agent, mixture or exposure circumstance for which there is inadequate evidence of carcinogenicity in humans but limited evidence of carcinogenicity in experimental animals together with supporting evidence from other relevant data may be placed in this group.

NIOSH (National Institute for Occupational Safety and Health, 2007): Ca ; Listed as: 3,3'-Dichlorobenzidine (and its salts)

Ca : NIOSH considers this substance to be a potential occupational carcinogen (See Appendix A in the NIOSH Pocket Guide to Chemical Hazards).

MAK (DFG, 2002): Category 2 ; Listed as: 3,3'-Dichlorobenzidine

Category 2 : Substances that are considered to be carcinogenic for man because sufficient data from long-term animal studies or limited evidence from animal studies substantiated by evidence from epidemiological studies indicate that they can make a significant contribution to cancer risk. Limited data from animal studies can be supported by evidence that the substance causes cancer by a mode of action that is relevant to man and by results of in vitro tests and short-term animal studies.

NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed

TOXICITY AND RISK ASSESSMENT VALUES

EPA IRIS

EPA Risk Assessment Values for CAS91-94-1 (U.S. Environmental Protection Agency, 2011):

Oral:

Slope Factor: 4.5x10(-1) per mg/kg-day
RfD:

Inhalation:

Unit Risk:
RfC:

Drinking Water:

Unit Risk: 1.3x10(-2) per mg/L

TOXICITY VALUES

3,3'-DICHLOROBENZIDINE DIHYDROCHLORIDE SALT: References: ACGIH, 1991 ATSDR, 1998 Hathaway et al, 1996 HSDB, 2001 IARC, 1982 Lewis, 2000 Lewis, 1992 RTECS, 2001 Sittig, 1991
- LD50- (ORAL)RABBIT:
- LD50- (ORAL)RAT:
References: ACGIH, 1991 ATSDR, 1998 Hathaway et al, 1996 HSDB, 2001 IARC, 1982 Lewis, 2000 Lewis, 1992 RTECS, 2001 Sittig, 1991
- LD50- (ORAL)MOUSE:
- LD50- (ORAL)RAT:
- TD- (ORAL)RAT:
- TD- (SUBCUTANEOUS)RAT:
- TDLo- (ORAL)DOG:
- TDLo- (ORAL)HAMSTER:
- TDLo- (ORAL)MOUSE:
- TDLo- (SUBCUTANEOUS)MOUSE:
- TDLo- (ORAL)RAT:
- TDLo- (SUBCUTANEOUS)RAT:

CALCULATIONS

AMBIENT CONVERSIONS

CONVERSION FACTORS

1 ppm = 0.0966 mg/m(3) (ATSDR, 1998; HSDB , 2001)

1 mg/m(3) = 10.35 ppm (ATSDR, 1998)

-STANDARDS AND LABELS

WORKPLACE STANDARDS

ACGIH TLV Values for CAS91-94-1 (American Conference of Governmental Industrial Hygienists, 2010):

Editor's Note: The listed values are recommendations or guidelines developed by ACGIH(R) to assist in the control of health hazards. They should only be used, interpreted and applied by individuals trained in industrial hygiene. Before applying these values, it is imperative to read the introduction to each section in the current TLVs(R) and BEI(R) Book and become familiar with the constraints and limitations to their use. Always consult the Documentation of the TLVs(R) and BEIs(R) before applying these recommendations and guidelines.

Adopted Value

3,3'-Dichlorobenzidine

TLV:

TLV-TWA:
TLV-STEL:
TLV-Ceiling:

Notations and Endnotes:

Carcinogenicity Category: A3
Codes: L, Skin
Definitions:

A3: Confirmed Animal Carcinogen with Unknown Relevance to Humans: The agent is carcinogenic in experimental animals at a relatively high dose, by route(s) of administration, at site(s), of histologic type(s), or by mechanism(s) that may not be relevant to worker exposure. Available epidemiologic studies do not confirm an increased risk of cancer in exposed humans. Available evidence does not suggest that the agent is likely to cause cancer in humans except under uncommon or unlikely routes or levels of exposure.
L: Exposure by all routes should be carefully controlled to levels as low as possible.
Skin: This refers to the potential significant contribution to the overall exposure by the cutaneous route, including mucous membranes and the eyes, either by contact with vapors or, of likely greater significance, by direct skin contact with the substance. It should be noted that although some materials are capable of causing irritation, dermatitis, and sensitization in workers, these properties are not considered relevant when assigning a skin notation. Rather, data from acute dermal studies and repeated dose dermal studies in animals or humans, along with the ability of the chemical to be absorbed, are integrated in the decision-making toward assignment of the skin designation. Use of the skin designation provides an alert that air sampling would not be sufficient by itself in quantifying exposure from the substance and that measures to prevent significant cutaneous absorption may be warranted. Please see "Definitions and Notations" (in TLV booklet) for full definition.

TLV Basis - Critical Effect(s): Bladder cancer; eye irr
Molecular Weight: 253.13

For gases and vapors, to convert the TLV from ppm to mg/m(3):

[(TLV in ppm)(gram molecular weight of substance)]/24.45

For gases and vapors, to convert the TLV from mg/m(3) to ppm:

[(TLV in mg/m(3))(24.45)]/gram molecular weight of substance

Under Study

3,3'-Dichlorobenzidine

TLV:

TLV-TWA:
TLV-STEL:
TLV-Ceiling:

Notations and Endnotes:

Carcinogenicity Category: Not Listed
Codes: Not Listed
Definitions: Not Listed

TLV Basis - Critical Effect(s):
Molecular Weight:

For gases and vapors, to convert the TLV from ppm to mg/m(3):

[(TLV in ppm)(gram molecular weight of substance)]/24.45

For gases and vapors, to convert the TLV from mg/m(3) to ppm:

[(TLV in mg/m(3))(24.45)]/gram molecular weight of substance

AIHA WEEL Values for CAS91-94-1 (AIHA, 2006):

Not Listed

NIOSH REL and IDLH Values for CAS91-94-1 (National Institute for Occupational Safety and Health, 2007):

Listed as: 3,3'-Dichlorobenzidine (and its salts)
REL:

TWA:
STEL:
Ceiling:
Carcinogen Listing: (Ca) NIOSH considers this substance to be a potential occupational carcinogen (See Appendix A in the NIOSH Pocket Guide to Chemical Hazards).
Skin Designation: Not Listed
Note(s): See Appendix A

IDLH: Not Listed

OSHA PEL Values for CAS91-94-1 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):

Listed as: 3,'-Dichlorobenzidine; see 29 CFR 1910.1007
Table Z-1 for 3,'-Dichlorobenzidine; see 29 CFR 1910.1007:

8-hour TWA:

ppm:

Parts of vapor or gas per million parts of contaminated air by volume at 25 degrees C and 760 torr.

mg/m3:

Milligrams of substances per cubic meter of air. When entry is in this column only, the value is exact; when listed with a ppm entry, it is approximate.

Ceiling Value:
Skin Designation: No
Notation(s): Not Listed

OSHA List of Highly Hazardous Chemicals, Toxics, and Reactives for CAS91-94-1 (U.S. Occupational Safety and Health Administration, 2010):

Not Listed

ENVIRONMENTAL STANDARDS

EPA CERCLA, Hazardous Substances and Reportable Quantities for CAS91-94-1 (U.S. Environmental Protection Agency, 2010):

Listed as: [1,1[prime]-Biphenyl]-4,4[prime]-diamine,3,3[prime]-dichloro-
Final Reportable Quantity, in pounds (kilograms):

1 (0.454)

Additional Information:
Listed as: 3,3[prime]-Dichlorobenzidine
Final Reportable Quantity, in pounds (kilograms):

1 (0.454)

Additional Information:

EPA CERCLA, Hazardous Substances and Reportable Quantities, Radionuclides for CAS91-94-1 (U.S. Environmental Protection Agency, 2010):

Not Listed

EPA RCRA Hazardous Waste Number for CAS91-94-1 (U.S. Environmental Protection Agency, 2010b):

Listed as: [1,1[prime]-Biphenyl]-4,4[prime]-diamine, 3,3[prime]-dichloro-
P or U series number: U073
Footnote:
Listed as: 3,3[prime]-Dichlorobenzidine
P or U series number: U073
Footnote:
Editor's Note: The D, F, and K series waste numbers and Appendix VIII to Part 261 -- Hazardous Constituents were not included. Please refer to 40 CFR Part 261.

EPA SARA Title III, Extremely Hazardous Substance List for CAS91-94-1 (U.S. Environmental Protection Agency, 2010):

Not Listed

EPA SARA Title III, Community Right-to-Know for CAS91-94-1 (40 CFR 372.65, 2006; 40 CFR 372.28, 2006):

Listed as: 3,3'-Dichlorobenzidine
Effective Date for Reporting Under 40 CFR 372.30: 1/1/87
Lower Thresholds for Chemicals of Special Concern under 40 CFR 372.28:

DOT List of Marine Pollutants for CAS91-94-1 (49 CFR 172.101 - App. B, 2005):

Not Listed

EPA TSCA Inventory for CAS91-94-1 (EPA, 2005):

Listed as: [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dichloro-

SHIPPING REGULATIONS

SURFACE

DOT -- Table of Hazardous Materials and Special Provisions (49 CFR 172.101, 2005):

Not Listed

ICAO International Shipping Name (ICAO, 2002):

Not Listed

LABELS

NFPA

NFPA Hazard Ratings for CAS91-94-1 (NFPA, 2002):

Not Listed

-HANDLING AND STORAGE

SUMMARY

INDUSTRIAL CHEMICALS

Avoid procuring large amounts of 3,3'-dichlorobenzidine, and handle the chemical as a carcinogen. Consult with transportation authorities before transporting the material (HSDB , 2001).

HANDLING

Persons handling 3,3'-dichlorobenzidine should wear full body protective clothing, gloves, and pressure demand or continuous flow, full-face air respirators (Sittig, 1991).

STORAGE

CONTAINER

3,3'-Dichlorobenzidine should be handled as a carcinogen and transported in a watertight container with screw-cap or snap-top lids enclosed in a second unbreakable container. Fill the space between the two containers with absorbent material. Enclose the second container in a strong outer box and fill the outer box with shock absorbent material (HSDB , 2001).
Label containers appropriately showing container quantity and date it was acquired (HSDB , 2001).

ROOM/CABINET RECOMMENDATIONS

The storage area should be placed close to the laboratory (HSDB , 2001).
Segregate the cabinet storage and store 3,3'-dichlorobenzidine with other carcinogens (HSDB , 2001).

INCOMPATIBILITIES

There have been no reports of incompatibilities with 3,3'-dichlorobenzidine (NIOSH , 2001).

-PERSONAL PROTECTION

SUMMARY

RECOMMENDED PROTECTIVE CLOTHING - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

Wear positive pressure self-contained breathing apparatus (SCBA).
Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection.
Structural firefighters' protective clothing provides limited protection. fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.

Self-contained breathing apparatus, gloves, and protective clothing should be worn when exposed to 3,3'-dichlorobenzidine (OHM/TADS , 2001; Sittig, 1991).

RESPIRATORY PROTECTION

Refer to "Recommendations for respirator selection" in the NIOSH Pocket Guide to Chemical Hazards on TOMES Plus(R) for respirator information.

Pressure demand or continuous flow, full-face air respirators are recommended (Sittig, 1991).

PROTECTIVE CLOTHING

CHEMICAL PROTECTIVE CLOTHING. Search results for CAS 91-94-1.

Specific recommendations and test data for this chemical were not found in the available manufacturers' product literature. A complete list of consulted manufacturers and references is presented below.

ENGINEERING CONTROLS

Hepa filters used in the lab hoods, glove boxes and animal rooms can reduce the carcinogen in the air (HSDB , 2001).

-PHYSICAL HAZARDS

FIRE HAZARD

SUMMARY

Editor's Note: This material is not listed in the Emergency Response Guidebook. Based on the material's physical and chemical properties, toxicity, or chemical group, a guide has been assigned. For additional technical information, contact one of the emergency response telephone numbers listed under Public Safety Measures.
POTENTIAL FIRE OR EXPLOSION HAZARDS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)
- Combustible material: may burn but does not ignite readily.
- When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.
- Those substances designated with a "P" may polymerize explosively when heated or involved in a fire.
- Contact with metals may evolve flammable hydrogen gas.
- Containers may explode when heated.
- Runoff may pollute waterways.
- Substance may be transported in a molten form.

FLAMMABILITY CLASSIFICATION

NFPA Flammability Rating for CAS91-94-1 (NFPA, 2002):

Not Listed

FIRE CONTROL/EXTINGUISHING AGENTS

SMALL FIRE PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

Dry chemical, CO2 or water spray.

LARGE FIRE PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

Dry chemical, CO2, alcohol-resistant foam or water spray.
Move containers from fire area if you can do it without risk.
Dike fire control water for later disposal; do not scatter the material.

TANK OR CAR/TRAILER LOAD FIRE PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

Fight fire from maximum distance or use unmanned hose holders or monitor nozzles.
Do not get water inside containers.
Cool containers with flooding quantities of water until well after fire is out.
Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.
ALWAYS stay away from tanks engulfed in fire.

NFPA Extinguishing Methods for CAS91-94-1 (NFPA, 2002):

Not Listed

COMBUSTION TOXICITY

Very toxic fumes of chlorine, hydrochloric acid, and nitrogen oxides will be emitted if 3,3'-dichlorobenzidine is heated to decomposition (Lewis, 2000).

REACTIVITY HAZARD

A green color results from combining 3,3'-dichlorobenzidine with ferric chloride or bleaching powder (OHM/TADS , 2001).

Very toxic fumes of chlorine, hydrochloric acid, and nitrogen oxides will be emitted if 3,3'-dichlorobenzidine is heated to decomposition (Lewis, 2000).

EVACUATION PROCEDURES

SUMMARY

Editor's Note: This material is not listed in the Table of Initial Isolation and Protective Action Distances.

SPILL - PUBLIC SAFETY EVACUATION DISTANCES - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

Increase, in the downwind direction, as necessary, the isolation distance of at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids in all directions.

FIRE - PUBLIC SAFETY EVACUATION DISTANCES - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

PUBLIC SAFETY MEASURES - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)

CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number:

MEXICO:

SETIQ:

01-800-00-214-00 in the Mexican Republic;
For calls originating in Mexico City and the Metropolitan Area: 5559-1588;
For calls originating elsewhere, call: 011-52-555-559-1588.

CENACOM:

01-800-00-413-00 in the Mexican Republic;
For calls originating in Mexico City and the Metropolitan Area: 5550-1496, 5550-1552, 5550-1485, or 5550-4885;
For calls originating elsewhere, call: 011-52-555-550-1496, or 011-52-555-550-1552; 011-52-555-550-1485, or 011-52-555-550-4885.

ARGENTINA:

CIQUIME:

0-800-222-2933 in the Republic of Argentina;
For calls originating elsewhere, call: +54-11-4613-1100.

BRAZIL:

PRÓ-QUÍMICA:

0-800-118270 (Toll-free in Brazil);
For calls originating elsewhere, call: +55-11-232-1144 (Collect calls are accepted).

COLUMBIA:

CISPROQUIM:

01-800-091-6012 in Colombia;
For calls originating in Bogotá, Colombia, call: 288-6012;
For calls originating elsewhere, call: 011-57-1-288-6012.

CANADA:

CANUTEC:

613-996-6666 (Collect calls are accepted);
*666 cellular (in Canada only).

UNITED STATES:

CHEMTREC®:

1-800-424-9300 (Toll-free in the U.S., Canada, and the U.S. Virgin Islands);
703-527-3887 for calls originating elsewhere (Collect calls are accepted).

CHEM-TEL, INC.:

1-800-255-3924 (Toll-free in the U.S., Canada, and the U.S. Virgin Islands);
813-248-0585 for calls originating elsewhere (Collect calls are accepted).

INFOTRAC:

1-800-535-5053 (Toll-free in the U.S., Canada, and the U.S. Virgin Islands);
352-323-3500 for calls originating elsewhere (Collect calls are accepted).

3E COMPANY:

1-800-451-8346 (Toll-free in the U.S., Canada, and the U.S. Virgin Islands);
760-602-8703 for calls originating elsewhere (Collect calls are accepted).

NATIONAL RESPONSE CENTER (NRC):

1-800-424-8802 - (24 hours) (Toll-free in the U.S., Canada, and the U.S. Virgin Islands);
202-267-2675 for calls in the District of Columbia.

MILITARY SHIPMENTS:

703-697-0218 - Explosives/ammunition incidents (Collect calls are accepted);
1-800-851-8061 - All other dangerous goods incidents.

NATIONWIDE POISON CONTROL CENTER (United States only):

1-800-222-1222 (Toll-free in the U.S.).

For additional details see the section entitled "WHO TO CALL FOR ASSISTANCE" under the ERG Instructions.
As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.
Keep unauthorized personnel away.
Stay upwind.
Keep out of low areas.
Ventilate enclosed areas.

AIHA ERPG Values for CAS91-94-1 (AIHA, 2006):

Not Listed

DOE TEEL Values for CAS91-94-1 (U.S. Department of Energy, Office of Emergency Management, 2010):

Listed as Dichlorobenzidene 3,3'-
TEEL-0 (units = ppm): 0.2
TEEL-1 (units = ppm): 0.6
TEEL-2 (units = ppm): 4
TEEL-3 (units = ppm): 150
Definitions:

TEEL-0: The threshold concentration below which most people will experience no adverse health effects.
TEEL-1: The airborne concentration (expressed as ppm [parts per million] or mg/m(3) [milligrams per cubic meter]) of a substance above which it is predicted that the general population, including susceptible individuals, could experience notable discomfort, irritation, or certain asymptomatic, nonsensory effects. However, these effects are not disabling and are transient and reversible upon cessation of exposure.
TEEL-2: The airborne concentration (expressed as ppm or mg/m(3)) of a substance above which it is predicted that the general population, including susceptible individuals, could experience irreversible or other serious, long-lasting, adverse health effects or an impaired ability to escape.
TEEL-3: The airborne concentration (expressed as ppm or mg/m(3)) of a substance above which it is predicted that the general population, including susceptible individuals, could experience life-threatening adverse health effects or death.

AEGL Values for CAS91-94-1 (National Research Council, 2010; National Research Council, 2009; National Research Council, 2008; National Research Council, 2007; NRC, 2001; NRC, 2002; NRC, 2003; NRC, 2004; NRC, 2004; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; United States Environmental Protection Agency Office of Pollution Prevention and Toxics, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; 62 FR 58840, 1997; 65 FR 14186, 2000; 65 FR 39264, 2000; 65 FR 77866, 2000; 66 FR 21940, 2001; 67 FR 7164, 2002; 68 FR 42710, 2003; 69 FR 54144, 2004):

Not Listed

NIOSH IDLH Values for CAS91-94-1 (National Institute for Occupational Safety and Health, 2007):

Not Listed

CONTAINMENT/WASTE TREATMENT OPTIONS

SUMMARY

SPILL OR LEAK PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)
- ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area).
- Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.
- Stop leak if you can do it without risk.
- Prevent entry into waterways, sewers, basements or confined areas.
- Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.
- DO NOT GET WATER INSIDE CONTAINERS.
RECOMMENDED PROTECTIVE CLOTHING - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 153 (ERG, 2004)
- Wear positive pressure self-contained breathing apparatus (SCBA).
- Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection.
- Structural firefighters' protective clothing provides limited protection. fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
Contain spills using clay/bentonite dams, interceptor trenches, or impoundments. Swales should be constructed to divert uncontaminated water around the spill (OHM/TADS , 2001).

SMALL LEAK/SPILL

Sodium hypochlorite bleach is partially effective for 3,3'-dichlorobenzidine spills (HSDB , 2001).
Tetrapotassium pyrophosphate(5%) and sodium ethyl hexyl sulfate (10%) blended in a jet strayer proved to be effective in removing 3,3'-dichlorobenzidine from work areas (HSDB , 2001).

WASTE TREATMENT OPTIONS

CHEMICAL TREATMENT

Contaminated water may be treated by adding powdered or granular activated carbon or by chemical oxidation. Contaminated soil may be remediated by well point collection and treatment of leachates (OHM/TADS , 2001).
The addition of horseradish peroxidase and hydrogen peroxide to drinking water and wastewater containing 3,3'-dichlorobenzidine forms insoluble polymers which precipitate from the solution with a 99.9% removal efficiency. The precipitate may then be removed by filtration and sedimentation (Freeman, 1989).
Sodium hypochlorite bleach is partially effective for 3,3'-dichlorobenzidine spills (HSDB , 2001).
Tetrapotassium pyrophosphate (5%) and sodium ethyl hexyl sulfate (10%) blended in a jet strayer proved to be effective in removing 3,3'-dichlorobenzidine from work areas (HSDB , 2001).
Sodium dichromate in strong sulfuric acid can destroy 3,3'-dichlorobenzidine in 1-2 days (HSDB , 2001).
Wet-air oxidation, chemical or electronic oxidation, and carbon adsorption are also recommended technologies to treat 3,3'-dichlorobenzidine prior to land disposal (ATSDR, 1998).
An organic polyester resin or silicate fixation material should encapsulate 3,3'-dichlorobenzidine residue. The container with the compound may be packaged in 17H epoxy-lined drums and disposed at an approved EPA disposal site (OHM/TADS , 2001).
Waste management activities associated with material disposition are unique to individual situations. Proper waste characterization and decisions regarding waste management should be coordinated with the appropriate local, state, or federal authorities to ensure compliance with all applicable rules and regulations.

PHYSICAL TREATMENT

3,3'-Dichlorobenzidine may be incinerated in a rotary kiln incinerator at a temperature range of 820 -1600 degrees C. Liquids and gases may be incinerated in a matter of seconds, solids require several hours (HSDB , 2001).
Other incineration methods specify primary combustion at 820 degrees C for 0.5 seconds, and secondary combustion at 1200 degrees C for 1.0 second. The production of chlorine as a byproduct may be prevented by injecting steam or methane into the combustion process, and nitrogen oxides my be reduced by using thermal or catalytic devices (HSDB , 2001; Sittig, 1991).
High temperature incineration should be conducted using a hydrochloric acid scrubber or microwave plasma detoxification (OHM/TADS , 2001).

-ENVIRONMENTAL HAZARD MANAGEMENT

POLLUTION HAZARD

3,3'-Dichlorobenzidine has been detected in surface water, oil refinery and industrial effluents during the manufacture of pigments, resins, and plastics. It has also been found in land and water samples due to improper land disposal (ATSDR, 1998; Howard, 1989; IARC, 1982).

Engineering controls required in the workplace may reduce the releases to the environment (Howard, 1989).

It is not known to occur naturally (ATSDR, 1998; Howard, 1989; IARC, 1974; IARC, 1982).

In 347 sediment samples, 3,3'-dichlorobenzidine was not detected at 1 mg/kg dry weight (Howard, 1989).

ENVIRONMENTAL FATE AND KINETICS

3,3'-Dichlorobenzidine released to the atmosphere would likely associate with aerosols and particulates and settle from gravitation. Photodegradation is likely to be faster than dry deposition, but no studies on atmospheric fate are available to confirm this. The half-life for direct photolysis of 3,3'-dichlorobenzidine is 9.7 hours (ATSDR, 1998; Howard, 1989; HSDB, 2004).
The estimated half-life of 3,3'-dichlorobenzidine in air is 1-60 days (NSC , 2000).
The estimated photooxidation half-life of 3,3'-dichlorobenzidine is 0.905 to 9.05 hours in air (Howard et al, 1991).

WATER

SURFACE WATER
- It is expected 3,3'-dichlorobenzidine will remain dissolved in water and will not migrate from water to air based on the low Henry's law constant value (ATSDR, 1998).
- 3,3'-Dichlorobenzidine is unstable in surface water exposed to natural sunlight and air. It will photodegrade rapidly in these conditions; the half-life is approximately 90 seconds to 4.5 minutes (ATSDR, 1998; Howard et al, 1991; Howard, 1989; HSDB, 2004; NSC , 2000).
- The half-life in water with sunlight is approximately 1.5 minutes (Verschueren, 2001).
- In the noon-day summer sunlight, 3,3'-dichlorobenzidine has a strong absorption band at 282 nm and degrades rapidly in aqueous solutions (Howard, 1989; HSDB, 2004).
- The half-life for direct photolysis of 3,3'-dichlorobenzidine in distilled water is estimated to be 1.5-4.5 minutes (Howard et al, 1991; HSDB, 2004).
- 3-Chlorobenzidine and other water-insoluble colored degradation products are rapidly produced from 3,3'-dichlorobenzidine in shallow water via a photolytic reductive dechlorination process. After several hours, benzidine and other water-insoluble compounds are also produced (Howard, 1989; OHM/TADS , 2001).
- The estimated photooxidation half-life of 3,3'-dichlorobenzidine is 1.3 to 72.5 days in water (Howard et al, 1991).
- It is expected that 3,3'-dichlorobenzidine will be oxidized by metals in natural water, similar to its parent compound benzidine, although not as rapidly (Howard, 1989; HSDB , 2001).
- A recent study cited in ATSDR (1998) showed that after a year, 80% of 3,3'-dichlorobenzidine in aerobic conditions will biogedrade to benzidine in sediment/water(Nyman et al, 1997).
- 3,3'-Dichlorobenzidine irreversibly adsorbs to sediments and suspended particles; therefore the most probable fate is a chemical degradation within the sediment (Howard, 1989; HSDB, 2004; OHM/TADS , 2001).
- The distribution coefficient to natural sediments at pH 7, initially was very rapid. Adsorption was reduced by 30-50% at pH 9 and desorption was very low (Howard, 1989).
- Important fate processes in natural sediments and sewage sludge may include oxidative reactions involving metal cations which occur for benzidine, and may also occur for 3,3'-dichlorobenzidine (Howard, 1989; HSDB , 2001; OHM/TADS , 2001).
- Volatilization, hydrolysis, and microbial degradation are not expected to be important fate processes (Howard, 1989).
- Hydrolysis did not occur is tests involving freshwater in the dark at 21 degrees C after 30 days or in a sterile solution in the dark at 4 degrees C, pH 2-10, after 7 days (Verschueren, 2001).
GROUND WATER
- The half-life of 3,3'-dichlorobenzidine in groundwater is 8 weeks to 12 months based upon the estimated unacclimated aqueous aerobic biodegradation half-life (Howard et al, 1991).

SOIL

TERRESTRIAL
- 3,3'-Dichlorobenzidine adsorbs tightly to soil and sediments (Howard, 1989).
- Only about 2% dissipation occurred at 40 mg/kg soil after 6.5-8 months (Verschueren, 2001).
- 3,3'-Dichlorobenzidine in soil may cause chemical reactions. Under aerobic conditions, very slow mineralization may occur (2% in 32 weeks). Oxidation with naturally occurring soil cations such as Fe(3+) and Cu(2+) may be important (ATSDR, 1998; Howard, 1989; HSDB, 2004).
- It may be oxidized by metals in soil, similar to its parent compound benzidine, although not as rapidly (Howard, 1989; HSDB , 2001).
- Volatilization from soil is not expected to be a significant fate process. No loss of 3,3'-dichlorobenzidine due to volatilization occurred under anaerobic conditions after 52 weeks, and 32 weeks in aerobic conditions (Howard, 1989).
- 3,3'-Dichlorobenzidine is strongly adsorbed to Rubicon sand and Brookston clay loam. The distribution constant is 273 and 110, respectively (Howard, 1989).
- The half-life in soil based upon the estimated unacclimated aqueous aerobic biodegradation half-life is four weeks to six months (Howard et al, 1991).
- In soil the compound may last several months if the soil is kept away from sunlight (ATSDR, 1998).

OTHER

OTHER
- Acids can catalyze the photodegradation of 3,3'-dichlorobenzidine. The compound is much more stable to photodegradation in organic solvents and may persist in water contaminated with hydrocarbons (Howard, 1989).

ABIOTIC DEGRADATION

In the environment, 3,3'-dichlorobenzidine will strongly adsorb to soil and sediment. It is oxidized by metals in soil and water. Based on its Henry's Law Constant, 3,3'-dichlorobenzidine is not released to air from aquatic systems. It rapidly photodegrades in surface water. Sunlight affects its half-life in water and soil. Volatilization, hydrolysis, and microbial degradation are not important. If released to the atmosphere, it will photodegrade or associate with airborne particulates and aerosols and undergo gravitational settling (HSDB, 2004; NSC , 2000; ATSDR, 1998; Howard et al, 1991; Howard, 1989)

Hydrolysis is not expected to be an important fate process (Howard, 1989; HSDB, 2004).

BIODEGRADATION

3,3'-Dichlorobenzidine is resistant to biodegradation.This process is likely to occur slowly in water and soil (Howard, 1989; HSDB, 2004).

3,3'-Dichlorobenzidine is resistant to microbial degradation in freshwater lakes and activated sludge (HSDB, 2004).

Following one-month incubation time in the dark at 21 degrees C, 75% of 3,3'-dichlorobenzidine was still present. No metabolites were detected (Verschueren, 2001).

In laboratory biodegradability tests using sewage seed, biodegradation did not occur unless yeast extract was added. The elimination rate is thought to be enhanced by the growth of bacteria (Howard, 1989; HSDB, 2004; Verschueren, 2001).

In a die-away test, yeast extract concentrate was added to domestic sewage containing 3,3'-dichlorobenzidine. The results are as follows (Verschueren, 2001):
Yeast Extract Concentrate Elimination
100 mg/L 91%
200 mg/L 93%
400 mg/L 99%

No mineralization of 3,3'-dichlorobenzidine occurred under anaerobic conditions after one year (Howard, 1989; HSDB, 2004).

Under aerobic conditions, very slow mineralization may occur (2% in 32 weeks). Oxidation with naturally occurring soil cations such as Fe(3+) and Cu(2+) may be important (Howard, 1989; HSDB, 2004).

The half-life of 3,3'-dichlorobenzidine is four weeks to six months based on the unacclimated aerobic lake die-away and a soil die-away test (Howard et al, 1991).

Based on the estimated unacclimated aqueous aerobic biodegradation, the anaerobic half-life is 16 weeks to 24 months (Howard et al, 1991).

Less than 0.1% biodegradation was detected in 3,3'-dichlorobenzidine at 2 mg/L after 14 days in aerobic seawater (Verschueren, 2001).

BIOACCUMULATION

FISH

Bioconcentration of 3,3'-dichlorobenzidine will occur rapidly in fish. The higher bioconcentration factors occurring in non-edible parts (e.g., the head and viscera) were attributed to a higher lipid content (Howard, 1989; OHM/TADS , 2001).
3,3'-dichlorobenzidine bioaccumulates in freshwater fish at 5 ppb or 0.1 ppm. The chemical is cleared from the edible portions rapidly when fish are initially returned to uncontaminated water, but residues persist after 14 days (ATSDR, 1998).
Bluegill fish are capable of converting 3,3'-dichlorobenzidine to a water- soluble polar derivative, which is hydrolytically unstable, and can easily be reverted back to 3,3'-dichlorobenzidine (OHM/TADS , 2001).
Of 83 biota samples taken, 3,3'-dichlorobenzidine was not detected at a detection limit of 2.5 mg/kg (wet weight) (Howard, 1989; HSDB, 2004).

BIOCONCENTRATION FACTOR

BLUEGILL SUNFISH (Lepomis macrochirus): Whole Fish: 495-507 (Howard, 1989)
BLUEGILL SUNFISH (Lepomis macrochirus): Whole Fish: 500 (ATSDR, 1998)
BLUEGILL SUNFISH (Lepomis macrochirus): Edible parts: 114-170 (Howard, 1989)
BLUEGILL SUNFISH (Lepomis macrochirus): Edible parts: 114-175 (HSDB, 2004)
BLUEGILL SUNFISH (Lepomis macrochirus): Non-edible parts: 814-856 (Howard, 1989)
BLUEGILL SUNFISH (Lepomis macrochirus): 5-100 mcg/L for 96-168 hours: BCF=approximately 500 (Verschueren, 2001)
BLUEGILL SUNFISH (Lepomis macrochirus): 2 mg/L for 48 hours: BCF=265 (Verschueren, 2001)
BLUEGILL SUNFISH (Lepomis macrochirus): 0.5 mg/L for 120 hours: BCF=277 (Verschueren, 2001)
BLUEGILL SUNFISH (Lepomis macrochirus): 5 mcg/L for 96 hours: BCF: 495 (Verschueren, 2001)
GOLDEN IDLE (Leuciscus melanotus): 50 mcg/L for 3 hours BCF=610 (Howard, 1989; Verschueren, 2001)
ALGAE (Chlorella fusca): 50 mcg/L for 24 hours BCF=940 (Howard, 1989; Howard, 1989; Verschueren, 2001)
FISH (edible portions): BCF as high as 426 after 120 hours (OHM/TADS , 2001)

ENVIRONMENTAL TOXICITY

3,3'-DICHLOROBENZIDINE

Note: Values are from Verschueren, 2001 unless otherwise noted.
EC50 - (WATER) BACTERIA (Aeromonas hydrophila): >100 mg/L for 18H
EC50 - (WATER) BACTERIA (Photobacterium phosphoreum): 0.058 mg/L for 15M
EC50 - (WATER) BACTERIA (Pseudomonas fluroescens): >100 mg/L for 18H
EC50 - (WATER) CRUSTACEANS (Daphnia magna): 7-10 mg/L for 24H
EC50 - (WATER) CRUSTACEANS (Daphnia magna): 2-3 mg/L for 48H
EC90 - (WATER) BACTERIA (Spirillum volutans): 16 mg/L for 2H
EC100 - (WATER) CRUSTACEANS (Daphnia magna): 8.9 mg/L for 48H
LC0 - (WATER) GOLDEN ORFE (Leuciscus idus): 2.5 mg/L for 48H
LC0 - (WATER) ZEBRA FISH (Brachydanio rerio): 2.2 mg/L for 96H
LC50 - (WATER) BLUEGILL (Lepomis macrochirus): 0.5 mg/L for 120H
LC50 - (WATER) ZEBRA FISH (Brachydanio rerio): 3.2 mg/L for 96H
LC100 - (WATER) BLUEGILL (Lepomis macrochirus): 2 mg/L for 48H
LC100 - (WATER) ZEBRA FISH (Brachydanio rerio): 5 mg/L for 96H

3,3'-DICHLOROBENZIDINE DIHYDROCHLORIDE

Note: Values are from OMH/TADS, 2001 unless otherwise noted.
LD - (FRESHWATER) BLUEGILL (Lepomis macrochirus): 2 ppm for >48H
LC10 - (FRESHWATER) BLUEGILL (Lepomis macrochirus): 0.5 ppm for 72H
LD50 - (FRESHWATER) BLUEGILL (Lepomis macrochirus): 0.596 ppm for 120H

-PHYSICAL/CHEMICAL PROPERTIES

MOLECULAR WEIGHT

253.15

DESCRIPTION/PHYSICAL STATE

3,3'-Dichlorobenzidine is an crystalline aromatic amine, gray to purple in color. In air, it exists as dust particles or is bound to particulate matter. 3,3'-dichlorobenzidine is not a volatile chemcial and changes from a solid to a gas very slowly (ATSDR, 1998; NIOSH , 2001).

It forms needles from alcohol and benzene (Budavari, 2000; Lewis, 2000).

Dihydrochloride salt is stable and is described as a moist, colorless, white, or off-white needles or solid. The salt does not evaporate (ACGIH, 1991; ATSDR, 1998; Bingham et al, 2001; Hathaway et al, 1996; IARC, 1974; Lewis, 1998; NIOSH , 2001; Sittig, 1991).

weak base (IARC, 1974)

VAPOR PRESSURE

4.5x10(-9) mmHg (at 20 degrees C) (ACGIH, 1991; ATSDR, 1998)

4.2x10(-7) mmHg (at 25 degrees C) (estimated) (Howard, 1989)

FREEZING/MELTING POINT

FREEZING POINT

271 degrees F (NIOSH , 2001)

MELTING POINT

132-133 degrees C (ACGIH, 1991; ATSDR, 1998; Budavari, 2000; Howard, 1989; IARC, 1974; OHM/TADS , 2001; Sittig, 1991)
133 degrees C (Bingham et al, 2001; Lewis, 2000)
165 degrees C (Lewis, 1997)

BOILING POINT

368 degrees C (estimated) (ACGIH, 1991; Bingham et al, 2001)

402 degrees C (ATSDR, 1998; HSDB , 2001)

788 degrees F (NIOSH , 2001)

FLASH POINT

unknown (NIOSH , 2001)

AUTOIGNITION TEMPERATURE

350 degrees C (ACGIH, 1991)

EXPLOSIVE LIMITS

LOWER

unknown (NIOSH , 2001)

UPPER

unknown (NIOSH , 2001)

SOLUBILITY

IN WATER

3,3'-Dichlorobenzidine and dihydrochloride salt is insoluble or slightly soluble in water (ACGIH, 1991; Bingham et al, 2001; Lewis, 2000; Lewis, 1997).
0.07% (at 59 degrees F) (NIOSH , 2001)
3.1 mg/L (at 25 degrees C) (Howard, 1989)
3.1 mg/L (at 20 degrees C) (ATSDR, 1998)
4 mg/L (at 22 degrees C) (ATSDR, 1998)
700 ppm (at 25 degrees C) (OHM/TADS , 2001)
almost insoluble in cold water (IARC, 1974; OHM/TADS , 2001)

OTHER

It is soluble or readily soluble in benzene, glacial acetic acid, diethyl ether, ether, ethanol, and alcohol (ACGIH, 1991; ATSDR, 1998; Bingham et al, 2001; IARC, 1974; Lewis, 2000; Lewis, 1997).
Soluble or slightly soluble in dilute hydrochloric acid (IARC, 1974).

OCTANOL/WATER PARTITION COEFFICIENT

log Kow = 3.02 (HSDB , 2001)

log Kow = 3.21 (ATSDR, 1998)

log Kow = 3.5 (ATSDR, 1998)

log Kow = 3.51 (Howard, 1989)

HENRY'S CONSTANT

4.5x10(-8) atm-m(3)/mole (at 25 degrees C) (estimated) (Howard, 1989)

5.11x10(-11) atm-m(3)/mole (at 25 degrees C) (ATSDR, 1998)

SPECTRAL CONSTANTS

MASS

1771 (National Bureau of Standards EPA-NIH Mass Spectra Data Base) (HSDB , 2001)

-REFERENCES

GENERAL BIBLIOGRAPHY

40 CFR 372.28: Environmental Protection Agency - Toxic Chemical Release Reporting, Community Right-To-Know, Lower thresholds for chemicals of special concern. National Archives and Records Administration (NARA) and the Government Printing Office (GPO). Washington, DC. Final rules current as of Apr 3, 2006.

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3,3'-DICHLOROBENZIDINE

Classification | Information to evaluate chemical incidents

Information to evaluate chemical incidents

Information to evaluate chemical incidents

Information to evaluate chemical incidents