4-Amino-2-nitrophenol

log Kow = 0.96

0.96

less than 0.1 mg/mL at 70 °F (NTP, 1992)

Soluble in water, ethanol, diethyl ether; slightly soluble in dimethylsulfoxide

261 °F (NTP, 1992)

131 °C

4-amino-2-nitrophenol appears as dark red plates, needles or reddish-purple powder. Melting point 125-127 °C.

Dark red solid; [HSDB] Red-brown crystalline powder; [MSDSonline]

Danger

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

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P318, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Phenol, 4-amino-2-nitro-

Hazard Traits - Carcinogenicity

Phenol, 4-amino-2-nitro-: Does not have an individual approval but may be used under an appropriate group standard

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. Poisonous gases are produced in fire including nitrogen oxides. If materials or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local healty and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position.

Evacuate persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Dampen spilled material with 60 to 70% acetone to avoid airborne dust and remove to sealed containers for disposal. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear dust-proof chemical goggles and face shield unless full facepiece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

At any detectable concetration: SCBAF:PD,PP (any MSHA/NIOSH approved self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode); or SAF:PD,PP:ASCBA (any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary, self-contained breathing apparatus operated in a pressure-demand or other positive-pressure mode). Escape: HiEF (any air-purifying, full face-piece respirator with a high efficiency particulate filter); or SCBAE (any appropriate escape-type, self-contained breathing apparatus).

LC50 Pimephales promelas (fathead minnow) 34.3 (29.9-39.4) mg/L 96 hr, wt 150 mg, flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as CaCO3, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L CaCO3, temp: 26.4 + or - 1.4 °C, Purity 97%

LC50 Pimephales promelas (Fathead minnow, age 32 days) 36.2 mg/L/96 hr (confidence limit: 31.5-41.6 mg/L); flow through, 25.3 °C, pH 7.3, hardness 45.6 mg/L CaCO3, alkalinity 42.8 mg/L CaCO3, dissolved oxygen 7.6 mg/L /97% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 79(SRC), determined from a log Kow of 0.96(2) and a regression-derived equation(3), indicates that 4-amino-2-nitrophenol is expected to have high mobility in soil(SRC). Volatilization of 4-amino-2-nitrophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(4)). 4-Amino-2-nitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(5). Incomplete data were available regarding the biodegradation potential of 4-amino-2-nitrophenol(SRC, 2008); however, Nocardia v. was able to use this compound as a carbon source for limited growth under aerobic conditions(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 79(SRC), determined from a log Kow of 0.96(2) and a regression-derived equation(3), indicates that 4-amino-2-nitrophenol 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 2.3X10-12 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 its log Kow(2) and a regression-derived equation(6), suggests bioconcentration in aquatic organisms is low(SRC). Incomplete data were available regarding the biodegradation potential of 4-amino-2-nitrophenol(SRC, 2008); however, Nocardia v. was able to use this compound as a carbon source for limited growth under aerobic conditions(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-amino-2-nitrophenol, which has an estimated vapor pressure of 3.5X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-amino-2-nitrophenol 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 2.3 days(SRC), calculated from its rate constant of 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3) Particulate-phase 4-amino-2-nitrophenol may be removed from the air by wet or dry deposition(SRC). 4-Amino-2-nitrophenol contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Based on the data contained in this report, the CIR Expert Panel concludes that 2-amino-3-nitrophenol, 2-amino-4-nitrophenol,2-amino-4-nitrophenol sulfate, 2-amino-5-nitrophenol, 4-amino-3-nitrophenol, 3-nitro-p-hydroxyethylaminophenol, and 4-hydroxypropylamino-3-nitrophenol are safe as hair dye ingredients in the practices of use and concentration as described in this safety assessment, but the data are insufficient to make a determination of safety for 4-amino-2-nitrophenol.

Ingredients for which the data are insufficient and their use in cosmetics is not supported

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=119-34-6]

The Koc of 4-amino-2-nitrophenol is estimated as 79(SRC), using a log Kow of 0.96(1)and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-amino-2-nitrophenol is expected to have high mobility in soil. The pKa of 4-amino-2-nitrophenol is 7.81 (phenol)(4), indicating that this compound will partially exist in anion form in the environment, and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). However, anilines may bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(6,7), suggesting that mobility may be much lower in some soils(SRC).

/CASE REPORTS/ Contact allergy to 3-nitro-p-hydroxyethylaminophenol in a hair dye is described for the first time. p-Phenylenediamine is the most common screening allergen when allergic contact dermatitis is suspected, but sometimes the allergen is not sufficient for diagnosing allergic contact dermatitis to hair dyes. A 50-year-old woman developed a severe scalp dermatitis and developed vesicular hand eczema for the first time in her life. Patch testing was performed with the European Standard Series. The patch testing was supplemented with a local series of cosmetic allergens and the hairdresser's series. At the initial patch testing, there was a + reaction to nickel and a +? to PPD at days 3 and 7. Further, she reacted with a +? to her own hair collected at day 3 after the hair dying which elicited the dermatitis reaction. Open exposure to the product, which had initiated the dermatitis, was negative both before and after the allergic reaction to the product. None of the screening chemicals in the hairdresser's series gave a definite positive reaction. Only by patch testing with the individual hair dye product ingredients, the patient's reactions were explained. The patient gave a positive patch test to 4-amino-3-nitrophenol and 3-nitro-p-hydroxyethylaminophenol at days 3-4 reading.

/CASE REPORTS/ A liquid chromatography-tandem mass spectrometry (LC-MS-MS) analysis of biological fluids (blood, urine, gastric content, and bile) collected at autopsy in a case of suspected 2,4-dinitrophenol (DNP) fatal poisoning allowed the determination of DNP and its known metabolites (2-amino-4-nitrophenol and nitro-4-aminophenol). The tentative identification of three conjugated metabolites (DNP glucuronide, DNP sulfate, and 2-amino-4-nitrophenol glucuronide) could be made on the basis of their pseudomolecular ion, isotopic and fragmentation patterns, and retention characteristics. Another DNP metabolite reported in the literature, 2,4-diaminophenol, was not detected in the samples. Postmortem blood concentrations were 48.4 mg/L for DNP and 1.2 mg/L for 2-amino-4-nitrophenol. ...

4-Amino-2-nitrophenol

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

4-Amino-2-nitrophenol

An estimated BCF of 3 was calculated for 4-amino-2-nitrophenol(SRC), using a log Kow of 0.96(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 4-amino-2-nitrophenol is estimated as 2.2X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-amino-2-nitrophenol is expected to be essentially nonvolatile from water surfaces(2). 4-Amino-2-nitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(3).

A liquid chromatography-tandem mass spectrometry (LC-MS-MS) analysis of biological fluids (blood, urine, gastric content, and bile) collected at autopsy in a case of suspected 2,4-dinitrophenol (DNP) fatal poisoning allowed the determination of DNP and its known metabolites (2-amino-4-nitrophenol and nitro-4-aminophenol). The tentative identification of three conjugated metabolites (DNP glucuronide, DNP sulfate, and 2-amino-4-nitrophenol glucuronide) could be made on the basis of their pseudomolecular ion, isotopic and fragmentation patterns, and retention characteristics. Another DNP metabolite reported in the literature, 2,4-diaminophenol, was not detected in the samples. Postmortem blood concentrations were 48.4 mg/L for DNP and 1.2 mg/L for 2-amino-4-nitrophenol. ...

Yields 2,4-diaminophenol probably in rat. /From table/

A homologous series of hair dyes was selected for percutaneous absorption studies with excised human skin. The permeability constants obtained for the dyes were compared with octanol/water and skin membrane/water partition coefficients. The compounds examined were: p-phenylenediamine, o-phenylenediamine, 2-nitro-p-phenylenediamine, 2-amino-4-nitrophenol, 4-chloro-m-phenylenediamine, and 4-amino-2-nitrophenol. Skin absorption of the dyes was observed when they were applied in an aqueous solution. With one exception, the octanol/water partition coefficients were in the same rank order as the permeability constants. The determination of the partitioning of the hair dyes between water and either stratum corneum or epidermis was more complex. Preliminary stratum corneum/water partition studies resulted in values that were in the reverse order of skin permeation. When binding of the compounds to components of the membrane was saturated, the partition values more closely duplicated the rank order of permeability of the dyes. Prediction of percutaneous absorption of substances based on their partition coefficients may be confounded if these compounds are capable of binding to skin.

CIR ingredient: 4-Amino-2-Nitrophenol

Used to dye furs, to dye hair, and to etch copper printing plates; [HSDB]

Fur Dressing and Dyeing [Category: Industry]

4-Amino-2-nitrophenol is used in dyeing furs a beige or deep reddish brown. It is also used in hair dyes. /SRP: FORMER/

4-Amino-2-nitrophenol is used in the etching of copper printing plates.

... Used in hair dyes ... used in textile dye synthesis. /SRP: FORMER/

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

HEATING 3-NITROPHENYLHYDROXYLAMINE WITH SULFURIC ACID; NITRATION OF N-ACETYL-4-AMINOPHENOL FOLLOWED BY HYDROLYSIS WITH DILUTE SULFURIC ACID; REDUCTION OF 4'-HYDROXY-3'-NITROAZOBENZENE-4-SULFONIC ACID; REACTION OF 3-NITRO-1-AZIDOBENZENE WITH DILUTE SULFURIC ACID

4-Amino-2-nitrophenol is used in dark-brown (at levels of 0.1%), medium-red (1.5%) and auburn (0.4% dye formulations and in bleach toner formulations for silver (at levels of 0.002%), platinum-blond (0.02%), ash-blond (0.05%) and golden-blond (0.2%) shades. /SRP: FORMER/