2,4-Diaminotoluene

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Amines, Aromatic

Carcinogens

log Kow = 0.14

0.14

0.35

0.14

1.045 at 212 °F (NTP, 1992) - Denser than water; will sink

1.26 kg/l

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

1.05 (liquid at 212 °F)

1.05 (Liquid at 212 °F)

Needles from water; crystals from alcohol

Prisms from alcohol

Colorless crystals

1 to 5 mg/mL at 70 °F (NTP, 1992)

Very soluble in water, ethanol, ethyl ether; soluble in acetone, carbon disulfide

Soluble in water, alcohol, and ether

Solubility in water, g/100ml at 20 °C: 3.5

Soluble

300 °F (NTP, 1992)

[ICSC] 149 °C

149 °C

149 °C

300 °F

300 °F

558 °F at 760 mmHg (NTP, 1992)

292 °C

292 °C

558 °F

292 °C @760 [mm Hg]

558 °F

210 °F (NTP, 1992)

99 °C

99 °C

99 °C

210 °F

99 °C

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P264, P270, P272, P273, P280, P301+P316, P302+P352, P317, P318, P319, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P316, P302+P352, P305+P351+P338, P317, P318, P319, P321, P330, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Chemical: 1,3-Benzenediamine, 4-methyl-

Hazard Traits - Carcinogenicity; Hematotoxicity; Hepatotoxicity and Digestive System Toxicity; Neurotoxicity; Respiratory Toxicity

1,3-Benzenediamine, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Benzenediamine, 4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 21-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13465

Substance: 4-methyl-m-phenylenediamine (toluene-2,4-diamine)

Special Hazards of Combustion Products: Toxic fumes are generated when heated.

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Excerpt from NIOSH Pocket Guide for Toluenediamine:

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

Exposure to toluene-2,4-diamine is primarily occupational. Acute (short-term) exposure to high levels of toluene-2,4-diamine in humans has caused severe skin and eye irritation sometimes leading to permanent blindness. Other effects include respiratory problems, stomach gas, rise in blood pressure, dizziness, convulsions, fainting, and coma. No information is available regarding the chronic (long-term) or carcinogenic effects of toluene-2,4-diamine in humans. Chronic animal studies have reported liver injury. In animal studies, toluene-2,4-diamine was carcinogenic following dietary administration, producing a significant increase in the incidence of a large variety of tumor types, including liver, mammary gland, subcutaneous fibromas, lung lymphomas, and leukemia. EPA has classified toluene-2,4-diamine as a Group B2, probable human carcinogen.

A skin, eye, and respiratory tract irritant; May cause skin sensitization, methemoglobinemia, and liver injury; Can be absorbed through skin; Possible carcinogen and mutagen; [ICSC] Commercially relevant products containing 2,4-toluylenediamine are 2,4/2,6-TDA (80/20) with 80% 2,4-TDA and 20% 2,6-TDA (CAS# 25376-45-8) and 2,4/2,6-TDA (65/35) with 65% 2,4-TDA and 35% 2,6-TDA (both produced as mixtures); 2,4-TDA of approximately 99% purity is also produced; [CPS&Q: RARs - Final Risk Assessment Report] Danger of skin sensitization; [MAK] May causes irritation and skin sensitization; Toxic by ingestion; Harmful by skin absorption; Prolonged or repeated ingestion exposure may cause damage to the kidneys, liver, blood, bladder, and reproductive system; Suspected mutagen and reproductive toxicant; Possible carcinogen; [Alfa Aesar MSDS]

3418 151

1709 151

1709 151

3418 151

1709 151(2,4-Toluenediamine)

NIOSH; Current Intelligene Bulletin No 53 Toluene Diisocyanate (TDI) and Toluenediamine (TDA): Evidence of Carcinogenicity. (1989)

DHEW/NCI; Bioassay of 2,4-Diaminotoluene for Possible Carcinogenicity (1979) Technical Rpt Series No. 162 DHEW Pub No. (NIH) 79-1718

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2,4-Diaminotoluene (95-80-7) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s057diam.pdf]

U221; As stipulated in 40 CFR 261.33, when toluenediamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). /Toluenediamine/

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Use water spray, foam, powder, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

General First Aid:

General First Aid:

General First Aid:

(General first aid procedures)

Well closed. Separated from oxidants and acids. Separated from food and feedstuffs. Store in an area without drain or sewer access. Do NOT store or transport in containers made from aluminium or copper and its alloys. Provision to contain effluent from fire extinguishing.

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Spillage Disposal. Personal protection: chemical protection suit including self-contained breathing apparatus. Do not let this chemical enter the environment. Do not wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations.

Spread over with 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton, stuffed with ruffled paper.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U221, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. /Toluenediamine/

Biodegradability in wastewater by activated-sludge was determined by evaluation of total org C (TOD) & COD removal efficiencies. 2,4-Diaminotoluene was easily decomposed.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for TOLUENE-2,4-DIAMINE (8 total), please visit the HSDB record page.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations.

Toluene-2,4-diamine concentrations of <0.01-5.7 ug/hr and <0.01-5.5 ng/L were reported as urinary elimination rates and plasma levels, respectively, of 15 factory workers exposed to thermal degradation products of TDI-based flexible foam and MDI-based polyurethane glue(1).

... In rats fed various combinations of 0.1% 2,4-diaminotoluene & 0.25% ethionine in diet, there was evidence of incr incidence of hepatocellular carcinomas over that in rats treated with 2,4-diaminotoluene alone.

The mutagenicity of 2,4-diaminotoluene in Ames's Salmonella/microsome test was remarkably enhanced by treatment with hydrogen peroxide. Therefore, identification of the major mutagenic reaction product of 2,4-diaminotoluene with hydrogen peroxide at room temperature has been performed. Red precipitates were produced in a 2 day reaction mixture and were column chromatographed on silica gel. 5 Fractions having mutagenic potency were obtained. The red crystalline needles, obtained as the major reaction product, were separated from fraction 2 and were subjected to high resolution mass spectrometry, (1)H and (13)C NMR spectrometry. The structure of the compound was determined to be 2,7-diamino-3,8-dimethylphenazine from physicochemical and chemical evidence. The compound induced 212 revertants/nmole in Salmonella typhimurium TA98 with 25 uL S9 per plate.

In studies of the metabolism of aromatic amines in the Ames/Salmonella assay, a rapid and quantitative conversion of the mutagenic and carcinogenic aromatic amine 2,4-diaminotoluene to a single product was observed. This product was only produced in the presence of methanol, and not other organic solvents. Isolation of this product showed that it was highly mutagenic in Salmonella TA98 with S9 activation. Characterization of the product of the interaction of methanol and 2,4-diaminotoluene indicated that methanol is activated to a reactive intermediate, probably formaldehyde by the 9000 X g supernatant used in the Ames/Salmonella assay. The formaldehyde subsequently reacts with 2,4-diaminotoluene to form the mutagenic product, identified as bis-5,5'(2,4,2',4-tetraaminotolyl)methane. Results of this study demonstrate that methanol may be an inappropriate solvent for mutation and metabolism studies of aromatic amines and possibly other chemicals, and that solvent xenobiotic interactions may in some cases lead to the misinterpretation of results.

2,4-Diaminotoluene, an aromatic amine hepatocarcinogen in rats and mice, reacts extensively with formaldehyde produced by the oxidation of methanol to form a single reaction product. Using (1)H and (13)C NMR and high resolution mass spectroscopy, this product was shown to be bis(2,4-diamino-5-tolyl)methane. This reaction product is shown to occur under conditions whereby methanol is metabolized to formaldehyde by rat hepatic postmitochondrial supernatant. These results demonstrate a novel reaction of aromatic amines and formaldehyde in biological samples and indicate that methanol as a solvent may become activated in vitro and produce complex interactions with solutes.

The carcinogenicity of 2,4-diaminotoluene in male Wistar rats fed diets containing 0.06% or 0.1% was antagonized by concomitant feeding of 3-methycholanthrene, alpha-naphthyl isothiocyanate or para-hydroxypropiophenone.

EC50; Species: Pseudokirchneriella subcapitata (Green Alga) exponential growth phase; Conditions: freshwater, static, 25 °C, pH 6.0-7.5; Concentration: 78.1 ug/L for 96 hr (95% confidence interval: 60-100.7 ug/L); Effect: decreased population abundance /formulation/

EC50; Species: Daphnia magna (Water Flea) age <24 hr, Lake Langedam strain; Conditions: freshwater, static, 20 °C, pH 7.8-8.0, hardness 250 mg/L CaCO3, dissolved oxygen 94-99%; Concentration: 12000 ug/L for 24 hr; Effect: intoxication, immobilization /98% purity/

EC50; Species: Daphnia magna (Water Flea) age <24 hr, Lake Langedam strain; Conditions: freshwater, renewal, 20 °C, pH 7.8-8.0, hardness 250 mg/L CaCO3, dissolved oxygen 94-99%; Concentration: 1600 ug/L for 48 hr; Effect: intoxication, immobilization /98% purity/

LC50; Species: Oryzias latipes (Japanese Medaka) age 28-43 days juvenile, weight 18-71 mg; Conditions: freshwater, flow through, 25 °C, pH 7.88, hardness 45.8 (38.0-52.0) mg/L CaCO3, alkalinity 45.9 (35.0-58.5) mg/L CaCO3, dissolved oxygen 6.8 mg/L; Concentration: 912000 ug/L for 96 hr (95% confidence interval: 797000-1040000 ug/L) /98% purity/

For more Ecotoxicity Values (Complete) data for TOLUENE-2,4-DIAMINE (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 1331 and 1346(2) indicate that toluene-2,4-diamine is expected to have low mobility in soil(SRC). The estimated pKa of toluene-2,4-diamine is 5.35(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(8,9), suggesting that mobility may be much lower in some soils(SRC). Volatilization of toluene-2,4-diamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.5X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Toluene-2,4-diamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.70X10-4 mm Hg at 25 °C(6). Utilizing a shake flask test and soil inoculum, 35% 14-CO2 evolution was reached in 375 days(7) indicating that biodegradation is not an important environmental fate process in soil.

AQUATIC FATE: Based on a classification scheme(1), Koc values of 1331-1346(2), indicate that toluene-2,4-diamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.5X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated pKa of 5.35(5) indicates toluene-2,4-diamine will exist partially in the cation form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(6), a BCF range of 1.9-3.3(7) suggests that bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), toluene-2,4-diamine, which has a vapor pressure of 1.70X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase toluene-2,4-diamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 1.92X10-10 cu cm/molecule-sec at 25 °C(3). Particulate-phase toluene-2,4-diamine may be removed from the air by wet and dry deposition(SRC). Toluene-2,4-diamine absorbs light at wavelengths of>294 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body by inhalation of its aerosol or vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Cough. Sore throat.

MAY BE ABSORBED! Redness.

Redness. Pain.

irritation eyes, skin, nose, throat; dermatitis; ataxia, tachycardia, nausea, vomiting, convulsions, resp depression; methemoglobinemia, cyanosis, headache, lassitude (weakness, exhaustion), dizziness, bluish skin; liver injury; [potential occupational carcinogen]

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of November 6, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-80-7]

U221; As stipulated in 40 CFR 261.33, when toluenediamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). /Toluenediamine/

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3-Benzenediamine, 4-methyl- is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Toluene-2,4-diamine produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Toluene-2,4-diamine is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). /Toluenediamine/

Data from studies on the rat, rabbit, mouse, guinea-pig, and dog exposed to diaminotoluenes (cutaneous, subcutaneous, intravenous, intraperitoneal, or oral by gavage) showed fast elimination rates. The elimination of radioactivity from various tissues in rodents followed a well-defined biphasic pattern. Rapid elimination over 7 hr was followed by a rather slow decline in the isotopic contents of tissues. The half-lives of tissue elimination during the fast phase were 0.89, 0.43, and 1.51 hr for male mouse liver, kidneys, and blood, respectively. During the slow phase of elimination, the half-lives for liver, kidneys, and blood in male mice were 11.7, 9.1, and 12.6 hr, respectively. The half-lives of elimination of radioactivity, during the slow phase, were greater for muscle (23.9 hr) and skin (29.2 hr) than for any other tissue.

... In several rodent species the major urinary metabolite was 2,4-diamino-5-hydroxytoluene; n-acetyl & glucuronide conjugates were also found. In rats the major unconjugated metabolites in urine are 4-acetylamino-2-aminotoluene, 2,4-diacetylaminotoluene & 2,4-diacetylaminobenzoic acid.

When 2,4-tolylenediamine was incubated with liver cytosol from various species, or cytosol from various tissues of hamster or rabbit ... n-acetylation occurred selectively at the p-amino group of 2,4-tolylenediamine & to a smaller extent at the o-amino group. In hamsters & rabbits, the highest n-acetyltransferase activity was present in cytosol of liver, followed by that from kidneys, mucosal epithelium of intestine, & lungs. Hamster-liver cytosol had the greatest activity, followed by ... guinea pigs, rabbits, mice & rats. Only a trace of an n-acetyl derivative of 2,4-tolylenediamine was formed thru ... human liver cytosol ... .

... The 2,4-isomer was selectively N-acetylated at the p-amino group by liver cytosol prepared from hamsters, guinea-pigs, rabbits, mice, and rats. The cytosol from liver, kidney, intestinal mucosa, and lung of hamsters and rabbits was studied for N-acetyl transferase activity using 2,4-DAT and 4-acetylamino-2-amino-toluene as substrates. All tissues showed marked species differences in enzyme activity. Tissues with high N-acetyl transferase levels, such as liver, could produce both 4-acetylamino-2-aminotoluene and 2,4- diacetylaminotoluene. There were also sex differences in the N-acetylation capacity of the liver cytosol.

After a single ip injection of 2,4-DAT (77 mg/kg body weight) in male rats, 69.4% of the dose was eliminated in the urine and feces after 24 hr as a complex mixture of metabolites, indicating both free and conjugated derivatives. The major urinary metabolites identified were 4-acetylamino-2-aminotoluene, 2,4- diacetylaminotoluene, and 4-acetylamino-2-aminobenzoic acid. In mice, oxidation of the methyl group to a benzoic acid was the major reaction and the major urinary metabolites in mice were 4- acetylamino-2-aminobenzoic, 4-acetylamino-2-aminotoluene, and 2,4- diacetylaminobenzoic acid.

For more Metabolism/Metabolites (Complete) data for TOLUENE-2,4-DIAMINE (9 total), please visit the HSDB record page.

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

When (14)C-2,4-diaminotoluene was administered ip to male fisher rats, radioactivity in blood & plasma reached a maximum at 1 hr and decreased rapidly for 7 hr; 98.6% had been excreted after 5 days (76.5% in urine & 22.2% in feces).

Skin penetration by 5 substances that have been reported to be present in cosmetics was measured in vivo in humans, monkeys, and swine. The greatest skin penetration was recorded with 2,4-toluenediamine applied to the abdominal skin of monkeys and the least with 2,4-diaminoanisole on the monkey abdomen and human ventral forearm and with p-dioxane on the monkey ventral forearm. ... Crude estimates were made of the amt that might be absorbed through human skin under appropriate conditions of cosmetics use.

The results of skin penetration studies correspond with those from experimental animal studies. After 40 min of dermal contact, the highest rate of urinary excretion occurred 4 - 8 hr after exposure. During 24 hr of dermal contact, the highest absorption of 2,4-diaminotoluene resulted when test material was dissolved in acetone and applied to the skin of the forearm (23.7%).

Distribution varies with different species. However, data indicate that, in most species, the organs with the highest concentrations are the liver, kidneys, and adrenal glands. High concentrations are also observed in the gastrointestinal tract, while the lowest levels are found in the heart, gonads, brain, and blood. A dose-dependent binding of the 2,4-isomer to hepatic and renal proteins has been demonstrated.

For more Absorption, Distribution and Excretion (Complete) data for TOLUENE-2,4-DIAMINE (8 total), please visit the HSDB record page.

Toluene-2,4-diamine is used primarily in the production of toluene diisocyanate, which is used in the production of polyurethane. It is used as an intermediate in the synthesis of dyes and heterocyclic compounds. Other uses of toluene-2,4-diamine include enhancement of thermal stability in polyamides, fatigue resistance and dyeability in fibers, and the preparation of impact-resistant resins, polyimides with superior wire-coating properties, benzimidazolethiols (antioxidants), hydraulic fluids, urethane foams, fungicide stabilizers, and sensitizers for explosives.

Used as an intermediate for dyes, polymers, and other chemicals; Also used in hair dyes (banned by the EU in 2007); [HSDB] Allergic contact dermatitis in hairdressers; [Marks] Used mainly in the EU as an intermediate for toluylene diisocyanates (TDI); Very small quantities are also used to make dyes and other chemicals; [CPS&Q: RARs - Final Risk Assessment Report]

Dressing Hair [Category: Other]

Used in hair dye products

Chain extender and cross-linker, intermediate in organic synthesis of dyes, polymers, especially polyurethanes

Used to produce CI Sulphur Orange 1 dye via linkage to thiazole rings

(1978) 1.50X10+8 G (PRINCPL CUSTMS DISTS)

(1982) 9.03X10+7 G (PRINCPL CUSTMS DISTS)

2023: 50,000 - <250,000 lb

(1978) 2.98X10+11 G (2,4- & 2,6-ISOMERS)

(1982) 3.27X10+11 G (2,4- & 2,6-ISOMERS)

1,3-Benzenediamine, 4-methyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4229]

It is produced commercially ... by nitrating toluene to produce a dinitrotoluene mixture containing approximately 80% 2,4-isomer and 20% 2,6-isomer (with small amounts of 2,3- and 3,4-dinitrotoluene, followed by catalytic reduction to a mixture of the corresponding diamines.

Reduction of m-dinitrotoluene with iron and hydrochloric acid.

Toluenediamines are available as cast solids in drums and molten liquids in tank cars. /Toluenediamines/

... Available in the USA as commercial grade; however, most of this chemical is used as intermediate, without isolation, and is usually produced as part of mixture of about 80% 2,4- & 20% 2,6-diaminotoluene. Also produced in smaller amounts as part of a mixture containing about 65% 2,4- & 35% 2,6-diaminotoluene.

2,4-Diaminotoluene available in Japan /has/ ... purity, above 99%.

Developer 14

For more Formulations/Preparations (Complete) data for TOLUENE-2,4-DIAMINE (18 total), please visit the HSDB record page.

All Other Basic Organic Chemical Manufacturing

1,3-Benzenediamine, 4-methyl-: ACTIVE

From a commercial standpoint, the most important toluenediamine isomers are the meta, or 2,4- and 2,6-isomers, which are obtained as a mixture by hydrogenation of the corresponding dinitrotoluenes. ... About 4% of the 2,3- and 3,4-isomers are formed as byproducts during toluene dinitration, and the same isomeric diamines subsequently appear as impurities in the mixture of m-diamines. They can be removed by distillation and are sold as commercial o-toluenediamine.