2,4-Diaminoanisole

138.17

138.17

210-406-1

86SSM2N1X7

1578

2811|3077

DTXSID5041358

Needles from ether|Colorless solid (needles).

2922299090

61.3

-0.31 (est)

2,4-diaminoanisole appears as colorless needles. Primarily used (along with salts such as 2,4-diaminoanisole sulfate) as a component of hair & fur dye formulations. (NIOSH, 2016)

1.2±0.1 g/cm3

67-68 °C

221 °C

164.6±16.0 °C

1.619

Solubility in water: miscible

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.

0.047 mm Hg at 25 deg C (est)

Relative vapour density (air = 1): 4.77

Combustible Solid

Henry's Law constant = 7.2X10-10 atm-cu cm/molat 25 det C (est)

pKa = 5.15 (est)

Crystalline powder. MW: 211.07. Soluble in water. /Dihydrochloride/|Hydroxyl radical reaction rate constant = 2.0X10-13 cu cm/molec-sec at 25 °C (est)

No rapid reaction with air. No rapid reaction with water.

Ethers

2,4-DIAMINOANISOLE is incompatible with the following: Strong oxidizers (NIOSH, 2016).

Combustible Solid

III

6.1(b)

2811

3

45-22-51/53-68

53-45-61

BZ8580500

T,N

Separated from strong oxidants. Well closed.

P201-P273-P281-P308 + P313

H302-H341-H350-H411

Incineration: Pour or sift onto a thick layer of sand and sodium carbonate mixture (90-10). Mix and shovel into a heavy paper box with much paper packing. Burn in incinerator. Fire may be augmented by adding excelsior and scrap wood. Waste may be dissolved in flammable solvent (alcohol, benzene, etc) and sprayed into fire box of an incinerator with afterburner and scrubber.|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/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for 2,4-DIAMINOANISOLE (6 total), please visit the HSDB record page.

Strong oxidizers.

Coal tar hair dyes posing a risk of cancer. (a) The principal display panel of the label and any labeling accompanying a coal tar hair dye containing any ingredient listed in paragraph (b) of this section shall bear, in accordance with the requirements of §740.2, the following: Warning-Contains an ingredient that can penetrate your skin and has been determined to cause cancer in laboratory animals. (b) Hair dyes containing any of the following ingredients shall comply with the requirements of this section: (1) 4-methoxy-m-phenylenediamine (2,4-diaminoanisole) and (2) 4-methoxy-m-phenylenediamine sulfate (2,4-diaminoanisole sulfate).

FISHBEIN L; A SURVEY OF TECHNIQUES FOR ESTIMATING AND MONITORING AROMATIC AMINES OF MAJOR INDUSTRIAL IMPORTANCE; IARC SCI PUBL 4(40) P75 (1981). REVIEW OF TECHNIQUES FOR ESTIMATION AND MONITORING OF AROMATIC AMINES INCLUDING 2,4-DIAMINOANISOLE.|DHHS/NIOSH; Current Intelligence Bulletins: 2,4-Diaminoanisole (1986) DHHS (NIOSH) Pub No. 86-124|Bioassay of 2,4-Diaminoanisole sulfate for Possible Carcinogenicity (1978) Technical Rpt Series No. 84 DHEW Pub No. (NIH) 78-1334, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)|Combustible.

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, and P501|Aggregated GHS information provided by 41 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|Warning|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P332+P313, P405, and P501|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|For more Personal Protective Equipment (PPE) (Complete) data for 2,4-DIAMINOANISOLE (7 total), please visit the HSDB record page.|(See protection codes)

Powder, water spray, foam, carbon dioxide.

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/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for 2,4-DIAMINOANISOLE (13 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

NIOSH considers 2,4-diaminoanisole (and its salts) to be a potential occupational carcinogens.|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.|NIOSH considers 2,4-diaminoanisole (and its salts) to be potential occupational carcinogens. Minimize occupational exposure (especially skin exposures).

Personal protection: chemical protection suit including self-contained breathing apparatus. Sweep spilled substance into sealable containers. Do NOT let this chemical enter the environment.

Separated from strong oxidants. Well closed.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

This substance is possibly carcinogenic to humans.

NO open flames.

See EFFECTS OF LONG-TERM OR REPEATED EXPOSURE. AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

SEDIMENT; 2,4-Diaminoanisole was detected in sediment at 1 out of 12 sites along the Taihu Lake, China at a concentration of 7.95 mg/kg(1).

The mutagenicity of aromatic amines, as measured by the Salmonella/microsome assay, was inactivated by ozone treatment.|Phenobarbital (75 mg/kg ip at 72, 48, and 24 hr previously) pretreatment of rats reduced the LD50 of 2,4-diaminoanisole from 116 to 97 mg/kg, and increased the initial rate of urinary excretion.|8 Kinds of o- and m-phenylenediamine (PD) derivatives, which are used as oxidative-type hair dyes, were treated with hydrogen peroxide (H2O2). Both before and after H2O2 treatment, their mutagenicity was tested by using Salmonella typhimurium TA98 in the presence or absence of a mammalian metabolic activation system (S9 mix). After H2O2 treatment, the mutagenic potencies of p-nitro-o-phenylenediamine, 3,4-diaminotoluene, p-nitro-m-phenylenediamine and 2,4-diaminophenol did not vary or slightly increased in comparison with those of the starting materials. The mutagenicity of o-PD, p-chloro-o-phenylenediamine (p-Cl-o-PD), m-PD and 2,4-diaminoanisole (p-OMe-m-PD) was enhanced remarkably by treatment with H2O2 and all the oxidation products required metabolic activation by S9 mix for their mutagenesis.|The effect of the carcinogenic hair dye component 2,4-diaminoanisole (2,4-DAA) on thyroid and pituitary morphology was studied. Heavy pigmentation of the hypertrophied thyroid epithelium was present when the animals were fed with 2,4-DAA for 6 weeks. Another hair dye component m-phenylenediamine (m-PDA), which lacks the methoxy group, and which is not carcinogenic, prevented the dark pigmentation of the thyroid epithelium caused by 2,4-DAA, but had only a slight effect on the hypertrophy of the gland. In the pituitary gland of 2,4-DAA-fed animals only a few aldehyde fuchsin positive thyrotrope cells were present. When 2,4-DAA and m-PDA were fed simultaneously, the number of hypertrophied chromophobic cells was greatly increased and the aldehyde fuchsin-positive cells were practically absent.|For more Interactions (Complete) data for 2,4-DIAMINOANISOLE (6 total), please visit the HSDB record page.

LD50 Rat ip 116 mg/kg|LD50 Rat oral 460 mg/kg|LD50 Rat oral >4000 mg/kg bw /2,4-Diaminoanisole sulfate in oil-in-water emulsion/|LD50 Rat ip 372 mg/kg bw /2,4-Diaminoanisole sulfate in dimethyl sulfoxide/

A bioassay of technical grade 2,4-diaminoanisole sulfate for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. 2,4-Diaminoanisole sulfate was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each species. The time-weighted average dietary concentrations used in the chronic bioassay were 0.12% for the low dose rats and 0.5% for the high dose rats. The dietary concentrations used for low and high dose mice were 0.12 and 0.24%, respectively. After a 78 wk period of chemical administration, observation of the rats continued for an additional 29 wk and observation of the mice continued for an additional 19 wk. For each species, 49 or 50 animals of each sex were placed on test as controls. In high dose male and female rat groups, the proportion of animals having one or more of the following malignant follicular cell thyroid tumors: papillary adenocarcinomas, follicular cell carcinomas, papillary cystadenocarcinomas, or adenocarcinomas, was significantly greater than the proportion in corresponding control groups. For high dose male rats the proportion of animals having either a C cell adenoma or a C cell carcinoma was also significantly increased. The incidence of malignant tumors (squamous cell carcinomas, basal cell carcinomas, or sebaceous adenocarcinomas) of the skin and its associated glands were significantly increased among high dose rats of both sexes. Among high dose female mice, the combined incidence of thyroid follicular cell adenomas and carcinomas was significantly increased. Among high dose male mice, the incidence of thyroid follicular cell adenomas was significantly increased, but no follicular cell carcinomas were observed. Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice: Positive; Female Mice: Positive. /2,4-Diaminoanisole sulfate/

2,4-Diaminoanisole's former production and use in the preparation of dyes, as an intermediate in the production of C.I. Brown 2, and as a corrosion inhibitor in steel(1) may have resulted 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 2,4-diaminoanisole is expected to have high mobility in soil(SRC). 2,4-Diaminoanisole is a weak base with an estimated pKa of 5.15(SRC), calculated by a method based on linear free energy relationships and perturbed molecular orbital theory(3). This estimated pKa indicates that 2,4-diaminoanisole will partially exist in the protonated form in acidic moist soils and cations generally adsorb to soils stronger than neutral molecules(4). Moreover, anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that the mobility of 2,4-diaminoanisole may be much lower in some soils than indicated by the estimated Koc value(SRC). Volatilization of 2,4-diaminoanisole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-10 atm-cu m/mole for the neutral species(SRC), using a fragment constant estimation method(7) and since cations will not volatilize. 2,4-Diaminoanisole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.047 mm Hg(SRC), determined from a fragment constant method(8). Biodegradation data were not available(SRC, 2006).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 53(SRC), determined from a structure estimation method(2), indicates that 2,4-diaminoanisole is not expected to adsorb to suspended solids and sediment(SRC). 2,4-Diaminoanisole is a weak base with an estimated pKa of 5.15(SRC), calculated by a method based on linear free energy relationships and perturbed molecular orbital theory(3). This estimated pKa indicates that 2,4-diaminoanisole will partially exist in the protonated form and cations generally adsorb to suspended solids and sediment stronger than neutral molecules(4). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant for the neutral species of 7.2X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6) and the fact that cations will not volatilize. According to a classification scheme(7), BCF values of 1.3 to 4.6 measured in fish(8), suggest bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-diaminoanisole, which has an estimated vapor pressure of 0.047 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 2,4-diaminoanisole 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 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 2,4-diaminoanisole 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 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,4-Diaminoanisole is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

A range of BCF values of 1.3 to 4.6 were measured for carp exposed to 2 ppm 2,4-diaminoanisole over the course of a 6 week incubation period(1). According to a classification scheme(2), this BCF range suggests bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,4-diaminoanisole can be estimated to be 53(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,4-diaminoanisole is expected to have high mobility in soil. 2,4-Diaminoanisole is a weak base with an estimated pKa of 5.15(SRC), calculated by a method based on linear free energy relationships and perturbed molecular orbital theory(3). This estimated pKa indicates that 2,4-diaminoanisole will partially exist in the protonated form in acidic moist soils and cations generally adsorb to soils more strongly than their neutral counterparts(4). Moreover, anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that the mobility of 2,4-diaminoanisole may be much lower in some soils than indicated by the estimated Koc value(SRC).

The Henry's Law constant for 2,4-diaminoanisole is estimated as 7.2X10-10 atm-cu m/mole for the neutral species(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4-diaminoanisole is expected to be essentially nonvolatile from moist soil and water surfaces(2). An estimated pKa of 5.15(SRC), calculated by a method based on linear free energy relationships and perturbed molecular orbital theory indicates 2,4-diaminoanisole will exist partially in the cation form at pH values of 5 to 9; therefore, volatilization from water surfaces is not expected to be an important fate process as cations do not volatilize. 2,4-Diaminoanisole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.047 mm Hg(SRC), determined from a fragment constant method(4).

SURFACE WATER; 2,4-Diaminoanisole was detected in water samples at 1 out of 12 sites in Taihu Lake, China at a concentration of 0.699 ppb(1).

CONSIDERABLE ATTENTION HAS BEEN FOCUSED RECENTLY ON SEVERAL SUBSTANCES /INCL 2,4-DIAMINOANISOLE/ USED IN DYEING HUMAN HAIR & ANIMAL FUR BECAUSE OF SEVERAL EPIDEMIOLOGICAL STUDIES INDICATING THAT HAIRDRESSERS WHO USE THESE SUBSTANCES OCCUPATIONALLY MAY HAVE HEIGHTENED INCIDENCE OF BLADDER CANCER. ... WHEN USED AS HAIR DYES, THESE AMINES ARE USUALLY MIXED WITH HYDROGEN PEROXIDE IMMEDIATELY BEFORE USE, PRODUCING...OXIDATION PRODUCTS THAT THEN REACT WITH SULFHYDRYL GROUPS PRESENT IN HAIR WITH THE FORMATION OF PERMANENT BOND.|NIOSH (1978) IN THE USA EST THAT APPROX 400,000 WORKERS WERE POTENTIALLY EXPOSED OCCUPATIONALLY TO 2,4-DIAMINOANISOLE. HAIRDRESSERS & COSMETOLOGISTS COMPRISED THE LARGEST PORTION OF THIS GROUP; A RELATIVELY SMALL NUMBER OF FUR DYERS WERE PROBABLY EXPOSED TO HIGHER LEVELS.|According to the 1981-1983 National Occupational Exposure Survey (NOES), about 23,000 workers in the US were exposed to 2,4-diaminoanisole or its sulfate salt, and these employees were all hairdressers or cosmetologists(1). Since 2,4-diaminoanisole is not currently used in the United States, occupational exposure and exposure to the general population should be very low or non existent; however, it's former use as a hair dye resulted in direct human exposure(SRC).

Following ip administration of 50 mg/kg bw (14)C-labelled 2,4-diaminoanisole to rats, 85% of radioactivity was excreted in urine and 9% in feces after 48 hr.|Injection of (3)H-2,4-diaminoanisole (10-200 mg/kg) into rats led to irreversible binding of liver and kidney proteins. Irreversibly bound material was preferentially localized in the microsomal fraction. Non-bound (3)H-2,4-diaminoanisole was rapidly cleared from plasma, liver and kidneys, whereas considerable amounts irreversibly bound could still be demonstrated 24 hr after a dose of 100 mg/kg ip.|Scalp penetration of 2,4-diaminoanisole (DAA) that occurs under conditions of hair dye usage was evaluated for both rhesus monkey and man using (14)C-labeled material. Average dose excretion of DAA in rhesus monkey was 0.02% and in man 0.015%.|No fixation of 2,4-diaminoanisole which passes through the cutaneous barrier is found in either liver or thyroid of hairless rats, 4 days after topical application.|For more Absorption, Distribution and Excretion (Complete) data for 2,4-DIAMINOANISOLE (7 total), please visit the HSDB record page.

Following ip administration of 50 mg/kg bw (14)C-labelled 2,4-diaminoanisole to rats... . Major metabolites were 4-acetylamino-2-aminoanisole, 2,4-diacetylaminoanisole, 2,4-diacetylaminophenol, 5-hydroxy-2,4-diacetylaminoanisole and 2-methoxy-5-(glycolamido)acetanilide or its isomer. These metabolites were excreted in urine both free and as glucuronides and sulfates.

To clarify the mechanism of carcinogenesis by hair dyes ... /the authors/ compared the extent of DNA damage induced by mutagenic m-phenylenediamine and 4-methoxy-m-phenylenediamine, using (32)P-5'-end-labeled DNA fragments obtained from the human c-Ha-ras-1 protooncogene and the p53 tumor suppressor gene. Carcinogenic 4-methoxy-m-phenylenediamine caused DNA damage at thymine and cytosine residues in the presence of Cu(II). Catalase and bathocuproine, a Cu(I)-specific chelator, inhibited 4-methoxy-m-phenylenediamine-induced DNA damage, suggesting the involvement of H2O2 and Cu(I). Superoxide dismutase (SOD) enhanced the DNA damage. Formation of 8-hydroxy-2'-deoxyguanosine (8-OH-dG) was induced by 4-methoxy-m-phenylenediamine in the presence of Cu(II). UV-visible spectroscopic studies have shown that Cu(II) mediated autoxidation of 4-methoxy-m-phenylenediamine and SOD accelerated the autoxidation. On the other hand, non-carcinogenic m-phenylenediamine did not cause clear DNA damage and significant autoxidation even in the presence of Cu(II). These results suggest that carcinogenicity of m-phenylenediamines is associated with ability to cause oxidative DNA damage ...

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Target Organs: Skin, thyroid, liver, reproductive system (NIOSH, 2016)|Carcinogens

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)

Fresh air, rest.

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

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

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 mg/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/|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/

/OTHER TOXICITY INFORMATION/ ... Carcinogenicity in man ... not been established.|/OTHER TOXICITY INFORMATION/ Ingredients found unsafe for use in cosmetics: Ingredient: 4-methoxy-m-phenylenediamine; Safety Concern: carcinogenicity. /From table/

2,4-diaminoanisole

The substance can be absorbed into the body through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

In Animals: irritation skin; thyroid, liver changes; teratogenic effects; [potential occupational carcinogen]

MAY BE ABSORBED!

Skin, thyroid, liver, reproductive system

In January 1978, NIOSH reported that approx 75% of the then current oxidation (permanent) hair-dyes formulations contained 2,4-diaminoanisole at levels of 0.05-2.0%, depending on the shade. Formulations for producing brown & blonde shades have been reported to contain significantly less 2,4-diaminoanisole than those for black shades.

1,3-Benzenediamine, 4-methoxy-: ACTIVE|2,4-diaminoanisole ... believed to be used as an intermediate in the manufacture of one commercially significant dye, CI basic brown 2. ... CI basic brown 2 was reported to be used mainly in dyeing acrylic fibers, although it was also present in variety of other products, including shoe polishes. 2,4-diaminoanisole and its sulfate may serve as oxidation bases in dyeing of furs.

A RAPID, SIMPLE & SENSITIVE GAS-LIQUID CHROMATOGRAPHIC METHOD WAS DEVELOPED FOR THE SIMULTANEOUS DETERMINATION OF 1,4-DIAMINOBENZENE, 2,5-DIAMINOTOLUENE & 2,4-DIAMINOANISOLE (POSSIBLE CARCINOGENS) IN PERMANENT (OXIDATION TYPE) HAIR DYES.|2,4-DIAMINOANISOLE IDENTIFICATION WAS MADE AFTER PRODUCTS WERE TRANSFORMED INTO HOMOGENEOUS SOLN BY SPECTRAL MEASUREMENTS OF PLATES, BY COLOR REACTIONS WITH DIFFERENT REAGENTS, OR BY RF VALUES. QUANTITATIVE DETERMINATION WAS BY DIRECT PHOTOMETRIC EVALUATION OF THE PLATES (DENSITOMETRY) AFTER COLOR FORMATION WITH REAGENTS DURING HAIR DYEING IN ORDER TO DETECT THE RATE OF TRANSFORMATION DURING USE.|2,4-DIAMINOANISOLE WAS DETERMINED IN HAIR DYES BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY.|Sample matrix: Hair dyes. Sample preparation: Separate on chromatography column. Assay procedure: High performance liquid chromatography with ultra violet detection. Limit of detection is not given. Sample matrix: Amine mixtures. Assay procedure: Thin layer chromatography. Limit of detection is not given.|Methods for the analysis of aromatic amines, including 2,4-diaminoanisole, in inks of ball-point and fibre-tip pens and watercolour paints, oxidative hair dyes, dyestuff mixtures and in paper, coloured textiles and leather products have been reported. These methods include differential pulse voltammetry, gas chromatography-mass spectrometry with mass ion detection, thin-layer chromatography, high-performance thin-layer chromatography and high-performance liquid chromatography with ultraviolet, diodearray or mass spectrometry detection.

Health Hazards -> Carcinogens