2,5-Diaminoanisole

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Reproductive effects in 8-week IP study with rats include decrease in number of pregnancies and live fetuses; Emergency treatment: Paraphenylenediamine; In sensitized individuals, paraphenylenediamine may cause allergic contact dermatitis following application as a hair dye and asthma following inhalation; Following ingestion, can cause angioneurotic edema, methemoglobinemia, acute tubular necrosis, and hepatotoxicity; An adult died after ingestion of 3 grams of p-phenylenediamine; Another adult who ingested 1800 mg developed angioneurotic edema and acute renal failure; [HSDB] See p-Phenylenediamine.

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)]

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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,4-Benzenediamine, 2-methoxy- is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

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.

... Groups of 60 male and female Sprague-Dawley rats 6-8 weeks of age received topical applications of an oxidative hair-dye formulation (7405) containing 0.4% 2-amino-4-nitrophenol, 6.0% 2,5-diaminoanisole sulfate, 2.0% resorcinol, 0.3% ortho-aminophenol, 5.0% oleic acid, 3.0% isopropanol, 0.2% sodium sulfite, 6.0% ammonia (29%) and water to 100%. The formulation was diluted in an equal volume of 6% hydrogen peroxide, and 0.5 mL was applied to a shaved area of the back (approx. 2.5 cm in diameter) twice a week up to week 117. Mean body weights and survival were similar in treated and control groups. No skin tumors were observed. The incidence of pituitary adenomas was increased in males in comparison with one of the control groups 35/52 (67%) versus 14/49; P < 0.01; X2-test), and no increase in the incidence of tumors at any other site was observed in treated as compared with control animals. ...

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that 2-methoxy-1,4-benzenediamine is expected to have very 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-methoxy-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 4.0X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2-Methoxy-1,4-benzenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-3 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 22(SRC), determined from a structure estimation method(2), indicates that 2-methoxy-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 4.0X10-11 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 -0.31(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-methoxy-1,4-benzenediamine, which has an estimated vapor pressure of 1.3X10-3 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-methoxy-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-methoxy-1,4-benzenediamine may be susceptible to direct photolysis by sunlight(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-methoxy-1,4-benzenediamine can be estimated to be 22(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-methoxy-1,4-benzenediamine is expected to have very 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).

/HUMAN EXPOSURE STUDIES/ Patch-test performed in humans with sensitization to aromatic amino compounds (paragroup allergy) revealed a sensibilization for the test compound similar to p-phenylenediamine.

/GENOTOXICITY/ 2,5-Diminoanisole resulted positive in vitro for genotoxicity in human skin fibroblasts for the induction of single strand breaks ... the purity of /2,5-diaminoanisole/ was not reported.

2-Methoxy-1,4-benzenediamine's former production and use as a hair dye component(1,2) may have resulted in its release to the environment through various waste streams(SRC). This compound is one of the 135 hair-dye substances banned by the European Union as of September, 2007(2).

An estimated BCF of 3 was calculated in fish for 2-methoxy-1,4-benzenediamine(SRC), using an estimated log Kow of -0.31(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-methoxy-1,4-benzenediamine is estimated as 4.0X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-methoxy-1,4-benzenediamine /is expected to be essentially nonvolatile from water and moist soil surfaces(2). 2-Methoxy-1,4-benzenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-3 mm Hg(SRC), determined from a fragment constant method(3).

/LABORATORY ANIMALS: Acute Exposure/ Sensitization was tested in Guinea pigs treated with 1% in paraffin oil of test compound as sulfate using the method of Magnusson and Kligman ( reaction evaluated at 24, 48, 72 hours). 3/10 animals showed a temporary skin-sensitization (very slight edema) and 1/10 a permanent skin sensitization (slight edema).

/LABORATORY ANIMALS: Acute Exposure/ 2,5-diaminoanisole (100 mg as the sulfate) applied on rabbits' eye gave in all animals a positive reaction with lesions to conjunctiva (redness: diffuse,crimson red , individual vessels not easily discernible; chemosis: obvious swelling with partial eversion of lid in two animals swelling with lids about half closed). The grade of ocular reaction was evaluated at 1, 2,3, 4, 7, 17, and 21 days. In another study in rabbits read at 1 hour, on days 1, 2, 3, 4, 7 the compound (Imexine OAN 0.5% in water ) did not result in irritation.

/LABORATORY ANIMALS: Acute Exposure/ Dermal irritation studies were carried out on rabbit using two different methods (a and b). The results showed that the compound has resulted "slightly irritating" (dose: 0.5 mL or 0.5 g in pasta, IIP = 0.8) in method (a) and mildly irritating (dose not reported, IIP = 1.1) in method (b).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 2,5-Diaminoanisole administered as the sulfate at 0, 1, 5, 25 mg/kg/day for 91 consecutive days by oral gavage to rats showed that 1 mg/kg/day represents the dose with "no-effect level". A similar study in dogs at 0, 1, 3, 9 mg/kg/day 7 days a week for 91 consecutive days gave "no-effect level" at 1 mg/kg/day.

For more Non-Human Toxicity Excerpts (Complete) data for 2-METHOXY-1,4-BENZENEDIAMINE (17 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of 2-methoxy-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-Methoxy-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(3), 2-methoxy-1,4-benzenediamine may be susceptible to direct photolysis by sunlight(SRC).

Occupational exposure to 2-methoxy-1,4-benzenediamine may have occurred through inhalation and dermal contact with this compound at workplaces where 2-methoxy-1,4-benzenediamine was produced or used. Use data indicate that the general population may have been exposed to 2-methoxy-1,4-benzenediamine via dermal contact with hair dye products containing 2-methoxy-1,4-benzenediamine. (SRC)

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-methoxy- is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

Skin absorption of a hair dye product with 2,5-DAA (1.9%, mixed 1:1 with H2O2) applied (27-32 min) on washed hair of 5 female volunteers was less than 0.102% of the amount applied, under hypothesis that distribution of the dye is equal in the whole body.

(14)C-2,5-DAA.2HCl (aqueous solution) applied epicutaneously without hydrogen peroxide on HIM: OFA-Sprague-Dawley rats at 2 mg (free base)/sq cm showed that 1.02% of the amount applied was absorbed. (14)C-2,5-DAA.2HCl in commercial preparation (1;1 with 6% H2O2) after epicutaneous applications on sq cm of clipped skin areas and 2 mg (free base)/sq cm on unclipped skin showed an absorption of 0.28% (clipped skin) and 0.07% (unclipped skin).

Used as a component in hair dyes; [HSDB]

Dressing Hair [Category: Other]

2,5 diaminoanisole is used in oxidative and developer hair dyes with couplers, such as m-phenylenediamine and m-dihydroxybenzenes (the resulting reactions produce different indo-amines of different color).

Oxidative (permanent) hair dye primary intermediate

Hair dye component /former/

Hair-dye substance banned by the European Union (September 2007)