2,5-Diaminoanisole

138.17

138.17

226-161-9

Z99H0MF010

DTXSID7063766

Crystals

2922299090

61.3

0.5

1.17g/cm3

103.5 °C @ Solvent: Benzene

299.1ºC at 760mmHg

159ºC

1.619

In water, 1.57X10+5 mg/L at 25 deg C (est)

1.32X10-3 mm Hg at 25 deg C (est)

Henry's Law constant = 3.98X10-11 atm-cu m/mol at 25 °C (est)

UV: 2112 (Absorption Spectra in the UV and visible Regions, Academic Press, New York) /o-Phenylenediamine, 4-methoxy/|Hydroxyl radical reaction rate constant = 2.01X10-10 cu cm/molec-sec at 25 °C (est)

P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P312, P304+P340, P304+P341, P312, P321, P322, P330, P333+P313, P342+P311, P363, P501

H302

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|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P312, P304+P340, P304+P341, P312, P321, P322, P330, P333+P313, P342+P311, P363, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

... 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. ...

LD50 Mouse oral 34 mg/kg bw|LD50 Rat ip 28 mg/kg bw|LD50 Rat oral 60 mg/kg bw

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).

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).

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).

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).

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).

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).

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)

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).

/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/ 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.

1,4-diamino-2-methoxybenzene

1,4-Benzenediamine, 2-methoxy-: ACTIVE

Thirty-nine common hair dye shampoos & solutions, including 2,5-diaminoanisole, were analyzed by ion-pair reversed-phase high-performance liquid chromatography.|Soap chromatography was used in separation & identification of amines, aminophenols, & phenols, including 2,5-diaminoanisole, in hair dyes. The system used a reversed-phase C18 column & UV detection at 254 nm.|Oxidative hair dyes, including 2,5-diaminoanisole, were analyzed by silica gel chromatography in hair coloring materials.