4-Amino-2-nitrophenol

154.12

154.12

204-316-1

N3499RCQ6B

56809

2811

DTXSID6020064

Dark-red plates or needles from water and ethanol

29222990

92.1

0.96

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

1.3617 (estimate)

131 °C

110 deg C at 12 mm Hg

156.1±23.7 °C

1.6890 (rough estimate)

H2O: <0.01 g/100 mL at 21 ºC

Prior to working with this chemical you should be trained on its proper handling and storage. Store in cool, dry place away from air and away from mineral acids and bases

3.5X10-5 mm Hg at 25 deg C (est)

Henry's Law constant = 2.2X10-12 atm-cu m/mole at 25 °C (est)

pKa = 7.81 at 25 °C (phenol)

When heated to decomposition it emits toxic fumes of NOx.|Hydroxyl radical reaction rate constant = 7.0X10-12 cu cm/molecule-sec at 25 °C (est)

Sensitive to oxidation upon prolonged exposure to air. Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

4-AMINO-2-NITROPHENOL may react with strong oxidizing agents, strong bases, acid chlorides and acid anhydrides (NTP, 1992).

UN 2811 6.1/PG 3

3

22-36/37/38-45

22-24/25-37/39-26-53-45

SJ6303000

Xn,T

Stable under normal temperatures and pressures. Stable at room temperature in closed containers under normal storage and handling conditions.

P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P501

H302

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.

Strong oxidizers, mineral acids, strong bases.

DHEW/NCI; Bioassay of 4-Amino-2-nitrophenol for Possible Carcinogenicity (1978) Technical Rpt Series No. 94 DHEW Pub No. (NIH) 78-1344

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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)

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. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

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. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|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).

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.

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.

LD50 Rat oral 3300 mg/kg /In oil-water emulsion/|LD50 Rat ip 302 mg/kg /In dimethylsulfoxide vehicle/

Groups of 50 rats and 50 mice of each sex were administered 4-amino-2-nitrophenol at one of two doses, either 1,250 or 2,500 ppm, for 103 weeks. Matched controls consisted of groups of 20 untreated rats and 20 untreated mice of each sex. All dosed and matched-control groups of each species and sex were killed at 105 weeks. Mean body weights of dosed rats of each sex were not appreciably affected by administration of the 4-amino-2-nitrophenol, and mean body weights of dosed mice of each sex were only slightly lower than those of corresponding matched controls. Survival of neither rats nor mice was affected by the test chemical, and sufficient numbers of animals in dosed and control groups were at risk for the development of late-appearing tumors. Since both male and female mice receiving 4-amino-2-nitrophenol had little or no depression in mean weights and their survival was comparable to that of controls, they may have been able to tolerate a higher dose. In rats, transitional-cell carcinomas of the urinary bladder showed a dose-related trend in the males (P < 0.001) and occurred at a significantly higher incidence (P = 0.018) in the high-dose males than in the matched-control males (controls 0/15, low-dose 0/46, high-dose 11/39 (28%)). Carcinomas of the bladder also occurred in one low-dose female and two high-dose females, but in none of the control females. Transitional-cell papillomas of the bladder occurred in two additional high-dose males, and transitional-cell hyperplasia of the bladder occurred in four additional high-dose males, but neither lesion occurred in control males. No tumors of the bladder were found among 220 male and 220 female historical-control rats at this laboratory. In mice, no tumors occurred in dosed groups of males or females at incidences that were significantly higher than those in the corresponding matched-control groups. Deposition of pigment occurred in the lamina propria of the small intestine in at least 91% of the animals in the dosed groups of rats and in at least 89% of the animals in the dosed groups of mice, but in none of the control groups of either species. It is concluded that under the conditions of the bioassay, 4-amino-2-nitrophenol was carcinogenic for male Fischer 344 rats, inducing transitional-cell carcinomas of the urinary bladder; the transitional-cell carcinomas of the urinary bladder observed in three dosed female rats may also have been associated with administration of the 4-amino-2-nitrophenol. The test chemical was not carcinogenic for male or female B6C3F1 mice at the doses tested.

4-Amino-2-nitrophenol's former production and use as a chemical intermediate in dyes for hair and textiles(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 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).

The rate constant for the vapor-phase reaction of 4-amino-2-nitrophenol with photochemically-produced hydroxyl radicals has been estimated as 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Amino-2-nitrophenol may react with nitrate radicals in the atmosphere(2). 4-Amino-2-nitrophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 4-Amino-2-nitrophenol contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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 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).

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).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 11,981 workers (9,309 of these were female) were potentially exposed to 4-amino-2-nitrophenol in the US(1). Occupational exposure to 4-amino-2-nitrophenol may have occurred through dermal contact with this compound at workplaces where this compound was produced or used(SRC). The general population may have been exposed to 4-amino-2-nitrophenol via inhalation and dermal contact with this compound and consumer products containing 4-amino-2-nitrophenol. (SRC)

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.

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/

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, upper respiratory tract and mucous membranes; and methemoglobinemia. ACUTE/CHRONIC HAZARDS: This material can cause irritation of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and NOx. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Aniline and related compounds/|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 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 ... . /Aniline 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. 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. Consider vasopressors if hypotensive with a normal fluid volume. 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. DIRECT PHYSICIAN ORDER ONLY ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

/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

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/

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

Two-dimensional thin-layer chromatography on silica gel G has been used to detect dye intermediates, including 4-amino-2-nitrophenol, in hair dyes at concentrations as low as 0.02%. Thin-layer chromatography on polystyrene-based anion exchangers and on microcrystalline cellulose and Cellex D anion exchangers has been used to separate primary aromatic amines, including 4-amino-2-nitrophenol.