2,5-Diaminotoluene

122.168

122.17

202-442-1

24JO8Z0RJU

DTXSID6029123

Plates from benzene|Colorless, crystalline tablets or plates from benzene

2921519090

52.04000

-0.22

Plates from benzene.

1.1±0.1 g/cm3

64 °C

273.5 °C

140.6±21.3 °C

1.636

Soluble in water, ethanol, ethyl ether; slightly soluble in benzene, acetic acid

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.

3.40X10-3 mm Hg at 25 deg C (est)

Henry's Law constant = 3.06X10-16 atm-cu m/mol at 25 °C (est)

READILY BECOMES OXIDIZED IN NEUTRAL OR ALKALINE SOLN TO FORM DARK PRODUCTS|Hydroxyl radical reaction rate constant = 2.0X10-10 cu cm/molec-sec at 25 °C (est)

III

6.1(b)

2811

R20/21

S24-S37-S45-S61

T: Toxic;N: Dangerous for the environment;

P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P333+P313, P337+P313, P363, P391, P405, P501

H301

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Evidence is given supporting testing of the class of compounds phenylenediamines for their toxic effects on human health and the environment. The results of toxicity testing of 22 compounds are tabulated as are the effects for which testing is being considered for 13 compounds, and the uses or potential uses of 47 phenylenediamines.[UNITED STATES EPA; PHENYLENEDIAMINES; RESPONSE TO INTERAGENCY TESTING COMMITTEE; FED REGIST 47(5) 973 (1982)]

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P321, P322, P330, P333+P313, P363, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P333+P313, P337+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 138 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P333+P313, P337+P313, P363, P391, P405, and P501|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P310, P302+P352, P305+P351+P338, P307+P311, P308+P313, P321, P330, P332+P313, P333+P313, P337+P313, P363, P405, and P501

0.1 mL of a 2.5% w/v solution of Toluene-2,5-diamine in 0.05% aqueous sodium sulphite (pH 7.0) was instilled into one eye of each of three rabbits. After 10 seconds the eye was rinsed with 50 mL of lukewarm water. Eyes were evaluated and scored according to the Draize scoring system at 1 hr and then at Days 1, 2, 3, 4, and 7. Mild conjunctival irritation was observed in 2 animals on days 1 and 3 respectively. Under the conditions of this test, a 2.5% toluene-2,5-diamine solution caused slight irritation to rabbit eyes.

U221; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

U221; As stipulated in 40 CFR 261.33, when 2-methyl-1,4-benzenediamine, 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).

LD50 Rat oral 102 mg/kg

A bioassay for possible carcinogenicity of 2,5-toluenediamine sulfate was conducted using Fischer 344 rats and B6C3F1 mice. 2,5-Toluenediamine sulfate was administered in the feed, at either of two concentrations, to groups of 50 males and 50 females of each species. The high and low time-weighted average concentrations of the compound were, respectively, 0.2 and 0.06% for rats and 0.1 and 0.6% for mice. Because compound administration to the high and low dose groups of each species was not begun simultaneously, each dosed group was assigned a control group. All control groups consisted of 50 animals, except for the high dose male and female rat control groups which were composed of 25 animals. The dosing period was for 78 weeks, followed by an additional 28 to 31 weeks of observation in rats and an additional 16 to 19 weeks in mice. Under the conditions of this bioassay, sufficient evidence was not obtained to demonstrate the carcinogenicity of 2,5-toluenediamine sulfate in either Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

2-Methyl-1,4-benzenediamine's production and use as a hair dye intermediate(1,2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 53(SRC), determined from a structure estimation method(2), indicates that 2-methyl-1,4-benzenediamine is expected to have high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 2-methyl-1,4-benzenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.4X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2-Methyl-1,4-benzenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(6). Biodegradation data in soil were not available(SRC, 2012).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 53(SRC), determined from a structure estimation method(2), indicates that 2-methyl-1,4-benzenediamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.4X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.16(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2012).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methyl-1,4-benzenediamine, which has an estimated vapor pressure of 3.4X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methyl-1,4-benzenediamine 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 0.6 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). By analogy to toluene-2,4-diamine which absorbs light at wavelengths >294 nm(4), 2-methyl-1,4-benzenediamine may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2-methyl-1,4-benzenediamine with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 0.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Methyl-1,4-benzenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). By analogy to toluene-2,4-diamine which absorbs light at wavelengths >294 nm(2), 2-methyl-1,4-benzenediamine may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for 2-methyl-1,4-benzenediamine(SRC), using an estimated log Kow of 0.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-methyl-1,4-benzenediamine can be estimated to be 53(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-methyl-1,4-benzenediamine is expected to have high mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC).

The Henry's Law constant for 2-methyl-1,4-benzenediamine is estimated as 7.4X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-methyl-1,4-benzenediamine is expected to be essentially nonvolatile from water and moist soil surfaces(2). 2-Methyl-1,4-benzenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-3 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to 2-methyl-1,4-benzenediamine may occur through inhalation and dermal contact with this compound at workplaces where 2-methyl-1,4-benzenediamine is produced or used(1,2). Data collected in 1989-1992 in a Danish survey on 1448 businesses indicated an estimated 0.044 tonnes of 2-methyl-1,4-benzenediamine were used in personal services, cleaning, and hair dressing, with an estimated 94,000 exposure events occurring annually(2). Use data indicate that the general population may be exposed to 2-methyl-1,4-benzenediamine via dermal contact with consumer products containing 2-methyl-1,4-benzenediamine(3).

A 50-mL solution composed of a typical hair dye formulation and water was used to suspend 1.4 g of toluene-2,5-diamine. The gel was applied to the abdominal skin of dogs for 3 hours (the number of dogs was not specified). The amount of toluene-2,5-diamine absorbed into the blood was determined using the Schiff base method. During the 3-hour exposure, the concentration of toluene-2,5-diamine increased to 1 mg/mL of blood. The concentration increased more rapidly during the later stage of the experiment than during the earlier stage. After the gel was removed and the area washed, the concentration in the blood decreased slowly. To determine the amount of toluene-2,5-diamine that had been absorbed through the skin, the absorption was imitated by a continuous intravenous infusion of toluene-2,5-diamine. An infusion of 0.022 mg of toluene-2,5-diamine per kilogram per minute was administered for 3 hours. During the first 2 hours, the concentration in the blood was greater than that seen in the absorption experiments; after 3 hours of infusion, the concentrations were the same. Because each dog weighed approximately 10 kg, it was calculated that 40 mg of toluene-2,5-diamine had been infused over the 3-hour period. Thus, it was assumed that the same amount was absorbed through the skin of the dogs in 3 hours.|In a ... series of studies regarding the amount of toluene-2,5-diamine absorbed in the blood and excreted in the urine, the addition of 3% hydrogen peroxide reduced absorption of toluene-2,5-diamine. After a 3-hour cutaneous exposure to a gel containing 3% hydrogen peroxide and 1.4 mg of toluene-2,5-diamine, no toluene-2,5-diamine was detected in the blood of dogs. An intravenous infusion of 0.0015 mg of toluene-2,5-diamine per kilogram of body weight per minute for 3 hours produced a detectable concentration of toluene-2,5-diamine. Thus, the absorption through the skin was less than 3 mg. Absorption of toluene-2,5-diamine was proved by the detection of small amounts (60-70 mg) in the urine.|A simple hair dye containing 2.5 g of toluene-2,5-diamine was applied to the hair and scalp of 5 human subjects for 40 minutes. Because humans excrete toluene-2,5-diamine as N,N'-diacetyl-p-toluenediamine (N,N'-dpt) rather than as a free amine, ethyl acetate, instead of chloroform, was used as the solvent for extracting this compound from the urine. The greatest rate of excretion was observed during the 5- to 8-hour period following the dyeing. On average, the total amount of N,N'-dpt excreted was 3.66 mg, which is equivalent to 2.17 mg of toluene-2,5-diamine.|To estimate the amount of toluene-2,5-diamine absorbed from the amount of the N,N'-dpt found in the urine, N,N'-dpt concentrations were determined using the same methods after subcutaneous injection of a known amount of toluene-2,5-diamine. Three women and 3 men were injected with 2.6 mL of a solution containing 5.54 mg of toluene-2,5-diamine. The rate of excretion was highest during the first few hours after the injection. An average of 4.5 mg of N,N'-dpt, or more specifically, 2.64 mg of toluene-2,5-diamine, was isolated from the urine; thus, 47.6% of the injected dose was excreted as N,N'-dpt. The authors calculated that 4.6 mg of toluene-2,5-diamine was either absorbed during the dyeing process or liberated in vivo from a compound formed during the preparation of the hair dye and absorbed through the skin.|For more Absorption, Distribution and Excretion (Complete) data for 2-METHYL-1,4-BENZENEDIAMINE (8 total), please visit the HSDB record page.

The Scientific Committee on Consumer Products of the European Commission reported that a 50% aqueous solution of toluene-2,5-diamine had greater than 99% high-performance liquid chromatography (HPLC) qualitative purity, 48% to 52% potentiometric titer purity, and the potential impurity o-toluidine less than 50 ppm.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

/HUMAN EXPOSURE STUDIES/ Patches of toluene-2,5-diamine (1% in petrolatum) were applied to the skin of 9 beauticians with allergic contact dermatitis. Readings were taken 72 hours after the patch was applied. Positive reactions were reported in 7 of the beauticians.|/HUMAN EXPOSURE STUDIES/ Toluene-2,5-diamine was tested for its sensitization potential in 31 men using the maximization test. Two percent aqueous toluene-2,5-diamine was used for induction and challenge. None of the subjects were sensitized.|/HUMAN EXPOSURE STUDIES/ In a multi-center study by the German Contact Dermatitis Group (DKG), 178 dermatitis patients (hairdressers) were patch tested with hairdressers' allergens in 11 centers. 18.0% were test positive to toluene-2,5-diamine, 8.4% to toluene-2,5-diamine sulfate, 18.0% to p-phenylenediamine base, 0.6% to resorcinol, 1.1% to 3-aminophenol, 2.2% to p-aminodiphenylamin hydrochloride, 3.4% to 4-aminophenol and 6.2% to o-nitro-p-phenylendiamine.|/HUMAN EXPOSURE STUDIES/ 597 dermatitis patients (hairdressers), of which 61.8% were current hair dressers, were patch tested in an IVDK multi-center study (1996-1998) in Germany with the patch test standard series and the hairdressers' series. 21.4% were positive to toluene-2,5-diamine, 18.1% were positive to p-phenylenediamine, 4.0% to p-aminophenol, 3.4% to m-aminophenol. Results from previous periods were also presented - 14.3% were tested positive to toluene-2,5-diamine in 1990-1991 and 16.2% in 1993-1995.|For more Human Toxicity Excerpts (Complete) data for 2-METHYL-1,4-BENZENEDIAMINE (8 total), please visit the HSDB record page.

2,5-diaminotoluene

1,4-Benzenediamine, 2-methyl-: ACTIVE|According to a survey of current use concentrations conducted by the Cosmetic, Toiletry, and Fragrance Association (CTFA), toluene-2,5-diamine is used at concentrations of 0.2% to 3.0% in hair dyes and colors.|2,5-Diaminotoluene was first produced commercially in the USA in 1920 (US Tariff Commission, 1921), but commercial production has not been reported since 1966 (US Tariff Commission, 1968).|Most manufacturers have reformulated their hair-coloring products to remove /2,5-toluenediamine/

Analytical methods for determining toluene-2,5-diamine in hair dyes: gas-liquid chromatography/flame ionization detector, detection limit 5.0 mg/L; thin-layer chromatography, detection limit 0.2 mg/L; high performance liquid chromatography with detection at UV wavelengths, detection limit not reported. /From table/|... Determination of 2,5-toluenediamine in hair dyes by two methods: (1) gravimetric determination of its diacetyl derivative and (2) an iodometric titration method ... . A simple colorimetric test for detection of aromatic amines, including 2,5-diaminotoluene, in hair dyes involves hydrochloric acid and vanillin in isopropyl alcohol.|High preformance liquid chromatographic determination of phenylenediamines, including 2-methyl-1,4-benzenediamine, in wastewater.|Determination of 2,5-diaminotoluene (0.4-1.17%) in hair dyes using high presure liquid chromatography. Detection at 235 nm was achieved using less than 10 nanogram concentration.|Determination of 2-methyl-1,4-benzenediamine in oxidative hair dyes by thin layer densitometry.

Cosmetics -> Hair dyeing