2-メチルベンゼン-1,4-ジアミン

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.

LC50; Species: Oryzias latipes (Japanese Medaka) length 2 cm, weight 0.2 g; Conditions: freshwater, static, 25 °C; Concentration: 16000 ug/L for 24 hr

LC50; Species: Oryzias latipes (Japanese Medaka) length 2 cm, weight 0.2 g; Conditions: freshwater, static, 25 °C; Concentration: 12000 ug/L for 48 hr

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).

On the basis of the data presented in this report the CIR Expert Panel concludes that toluene-2,5-diamine and toluene-2,5-diamine sulfate are safe as hair dye ingredients in the present practices of use and concentration as described in this safety assessment, but the availaale data are insufficient to support the safety of toluene-3,4 diamine as a hair dye ingredient

Safe for use in cosmetics, with qualifications

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 ability of 2,5-toluene diamine to induce morphological transformation was evaluated in secondary Syrian hamster embryo cells (Cell Transformation Assay). Results were not statistically calculated, but were based on the sensitivity of the positive control (benzo(a)pyrene). 2,5-Toluene diamine was tested at concentrations of 0.63, 1.25, 2.5, 5.0 or 10ug/ml, with relative cell survival ranging from 100% to 0%. Under highly sensitive conditions (positive control highly active), at least one transformed foci was observed at the two highest treatments. A second experiment tested at concentrations of 1.0, 1.5, 2.2, 3.3 or 5.0ug/ml, resulted in a range of 95% to 25% relative survival. Under less sensitive conditions (positive control weakly active), none of the treatments produced transformed foci. 2,5-Toluene diamine was considered to be weakly active in the cell transformation assay.

/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

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals

1987

1987

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).

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).

/LABORATORY ANIMALS: Acute Exposure/ An assessment of dermal irritation was conducted using New Zealand White rabbits. Toluene-2,5-diamine was applied as a 2.5% (wt/vol) preparation to the intact and abraded skin of 3 rabbits. Slight erythema and edema were observed at the intact site of all the animals. One rabbit had very slight erythema at the abraded site. The primary irritation index was estimated to be 0.3. No signs of irritation were observed after 72 hours.

/LABORATORY ANIMALS: Acute Exposure/ 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.

/LABORATORY ANIMALS: Acute Exposure/ A volume of 0.1 mL of Imexine OD (pH 9.71) was applied into the conjunctival sac of the left eye of one male rabbit; the right eye served as a control. The eye was not rinsed, and was evaluated and scored according to the Draize scoring system at 1, 24, 48, and 72 hr after application and then daily until Day 8. The test substance induced marked conjunctival irritation with chemosis and redness, slight iridial irritation and moderate to slight corneal opacity. All of these effects were reversible within 7-8 days. Under the test conditions, in which the test substance was applied undiluted and was not rinsed from the eye, the test substance was irritating to the rabbit eye. The high pH of the test solution may have contributed to the observed irritation.

/LABORATORY ANIMALS: Acute Exposure/ A single dose of 0.5 mL of Imexine OD (pH 9.71) was prepared on a dry compress and then applied to a 6 sq cm clipped area of the skin and covered with a semi-occlusive dressing for 4 hr. Skin reactions were evaluated 1 hr, 24 hr, 48 hr, and 72 hr after removing the dressing and then daily until day 6. No edema, ulceration or necrosis was noted. Evaluation of erythema was not possible due to the black coloration of the treatment site. Although the application of a 50.6% aqueous solution of Imexine OD produced no evidence of an edematous response after topical application under semi-occluded conditions in New Zealand White rabbits, an erythematous response could not be excluded due to black coloration of the treatment site by Imexine OD.

For more Non-Human Toxicity Excerpts (Complete) data for 2-METHYL-1,4-BENZENEDIAMINE (13 total), please visit the HSDB record page.

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).

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. 1,4-Benzenediamine, 2-methyl- is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

CIR ingredient: Toluene-2,5-Diamine

Used as a permanent hair dye; [Kanerva, p. 1840]

Dressing Hair [Category: Other]

Used as ingredients in the formulation of permanent hair dyes, colors and tints

Intermediate used in oxidation hair dyes

Toluene-2,5-diamine and toluene-2,5-diamine sulfate are used as primary intermediates in permanent hair dye formulations to produce black, drab and warm browns, and shades of blond and gray.

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.

2023: <50,000 lb

1,4-Benzenediamine, 2-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#5784]

Toluene-2,5-diamine can be manufactured by reductive cleavage of 4-amino-2,3'-dimethylazobenzene ...; reductive cleavage ...; electrolytic reduction of 2,5-dinitrotoluene... ; or condensation of 2-amino-1-methylbenzene and toluene-4-sulphonyl chloride to 4-toluenesolphono-2-toluidide, which is then coupled with diazotized aminobenzenesulphonic acid and reduced...

... By reductive cleavage of 4-amino-2,3'-dimethylazobenzene (ortho-aminoazotoluene) with tin & hydrochloric acid; reductive cleavage may also be carried out with zinc dust and hydrochloric acid. It can be prepared by electrolytic reductionn of 2,5-dinitrotoluene or by condensing 2-amino-1-methylbenzene and toluene-4-sulfonyl chloride to 4-toluenesulfono-2-toluidide, which is then coupled with diazotized aminobenzenesulfonic acid and reduced.

All Other Basic Organic Chemical Manufacturing

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/