2-Amino-5-nitrophenol

154.12

154.12

972974

204-503-8

0149H05U82

7087

2811

DTXSID1020063

Olive-brown, brown to orange crystalline solid|Orange needles when recrystallized from water

29222900

92.1

0.99 (est)

Rust brown to brown Crystalline Powder

1.3617 (estimate)

207-208 °C

322.46°C (rough estimate)

173.9±25.1 °C

1.6890 (rough estimate)

H2O: insoluble

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

3.52X10-5 mm Hg at 25 deg C (est)

Oral-rat LD50: 4000 mg/kg

Open flame is flammable; heated to decompose toxic nitrogen oxide gas

Henry's Law constant = 7.82X10-13 at 25 °C (est)

Hydroxyl radical reaction rate constant = 9.40X10-12 cu cm/molec-sec at 25 °C (est)

Is slowly oxidized by air at room temperature. Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

2-AMINO-5-NITROPHENOL is a mild reducing agent. Incompatible with strong oxidizing agents. Reacts slowly with oxygen in the air at room temperature. Stable at temperatures up to 140°F for two weeks when kept in the dark and under nitrogen. Stable under nitrogen for up to 24 weeks 77°F. Incompatible with strong bases (NTP, 1992). Incompatible with acid chlorides and acid anhydrides.

2811

2

36/37/38-68-20/21/22

26-36/37-45-36/37/39-36

SJ6302500

Xi,Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable under normal temperatures and pressures.

P261-P305 + P351 + P338

H315-H319-H335

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.

DHHS/NTP; Toxicology & Carcinogenesis Studies of 2-Amino-5-nitrophenol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 334 (1988) NIH Publication No. 88-2590

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

|Warning|H315 (95.79%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 2187 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

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 protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under 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)

moderately toxic

The LD50 of 2-amino-5-nitrophenol in rats has been reported to be greater than 4000 mg/kg bw by oral administration and greater than 800 mg/kg bw by ip injection ... .|LD50 Mouse oral >1250 mg/kg to < 2500 mg/kg|LD50 Rat oral >2500 mg/kg

Sixteen-Day and Thirteen-Week Studies: During the 16-day studies, F344/N rats of each sex received 0, 156, 313, 625, 1,250, or 2,500 mg/kg 2-amino-5-nitrophenol by gavage in corn oil vehicle. One of the five males that received 2,500 mg/kg, 1/5 females that received 1,250 mg/kg, and 2/5 females that received 313 mg/kg died before the end of the studies. Final mean body weights of rats that received 1,250 or 2,500 mg/kg were 11% and 30% lower than that of vehicle controls for males and 9% and 13% lower for females. B6C3F1 mice of each sex received doses of 0, 313, 625, 1,250, 2,500, or 5,000 mg/kg 2-amino-5-nitrophenol. Two of five males and 5/5 females that received 5,000 mg/kg, 3/5 males and 3/5 females that received 2,500 mg/kg, 3/5 females that received 1,250 mg/kg, 1/5 females that received 625 mg/kg, and 2/5 male vehicle controls died before the end of the studies. Final mean body weights of chemically exposed mice were not different from those of the vehicle controls. Rats that received 625, 1,250, or 2,500 mg/kg and male mice that received 5,000 mg/kg had loose stools. In 13-week studies, F344/N rats and B6C3F1 mice of both sexes received 0, 100, 200, 400, 800, or 1,600 mg/kg 2-amino-5-nitrophenol by gavage in corn oil. Five of 10 male and 2/10 female rats that received 1,600 mg/kg, 1/10 male and 3/10 female rats that received 800 mg/kg, and 1/10 male rats that received 400 mg/kg died before the end of the studies. Final mean body weights of males that received 400, 800, or 1,600 mg/kg were 10%, 25%, and 43% lower than that of vehicle controls. The final mean body weight of females that received 1,600 mg/kg was 16% lower that of vehicle controls. Four of 10 male and 3/10 female mice that received 1,600 mg/kg died before the end of the 13-week studies. The final mean body weight of male mice that received 1,600 mg/kg was 11% lower than that of vehicle controls; male and female mice that received 1,600 mg/kg appeared lethargic. During the 13-week studies, acute/chronic perivasculitis of vessels of the cecum and colon was observed in rats that received 400, 800, or 1,600 mg/kg and in mice that received 1,600 mg/kg.|Body Weight and Survival in the Two-Year Studies: Mean body weights of rats receiving 200 mg/kg were 5%-10% lower than those of vehicle controls after week 33 for males and 4%-5% lower than those of vehicle controls after week 93 for females. Survival of male rats was significantly lower than that of vehicle controls after week 99 for the 100 mg/kg dose group and after week 75 for the 200 mg/kg dose group (final survival: vehicle control, 33/50; 100 mg/kg group, 16/50; 200 mg/kg group, 4/50). Survival of female rats was comparable to that of vehicle controls (30/50; 32/50; 29/50). Loose or poorly formed stools were observed for male rats and occasionally for females that received 200 mg/kg. Mean body weights of mice that received 800 mg/kg were 8%-11% lower than those of vehicle controls between weeks 29 and 74 for males and 8%-13% lower than those of vehicle controls after week 69 for females; mean body weights of mice that received 400 mg/kg were greater than those of vehicle controls after week 69 for males and 5%-9% lower than those of vehicle controls after week 69 for females. Survival of mice that received 800 mg/kg was significantly reduced compared with that of vehicle controls after week 20 for males and week 22 for females and was not considered adequate to evaluate a carcinogenic response (final survival--male: vehicle control, 31/50; 400 mg/kg group, 36/50; 800 mg/kg group, 12/50; female: 37/50; 36/50; 10/50). Nonneoplastic and Neoplastic Effects in the Two-Year Studies: Pigmentation was present at increased incidences in all groups of chemically exposed animals and was characterized by varying amounts of an orange, granular pigment present in the fibrous connective tissue of the lamina propria, in the submucosa, and around vessels in the submucosa of the cecum and colon. Pigmentation of the rectum was observed at increased incidences in male rats that received 100 mg/kg, male and female rats that received 200 mg/kg, and both groups of chemically exposed mice. No pigmentation was found in the intestines of vehicle control rats or mice. Associated with pigmentation was an increased incidence of acute/chronic inflammation in the cecum and colon of all groups chemically exposed rats and mice; this inflammation was similar to that observed in the 13-week studies but was of greater severity. Acute/chronic inflammation was also present in the rectum of male rats that received 100 mg/kg, male and female rats that received 200 mg/kg, and male mice that received 800 mg/kg. The incidence of pancreatic acinar cell adenomas was significantly increased (P<0.002) in male rats that received 100 mg/kg 2-amino-5-nitrophenol (vehicle control, 1/50; 100 mg/kg, 10/50; 200 mg/kg, 3/49); the increase was considered to be associated with chemical exposure. The reduced survival of male rats that received 200 mg/kg markedly reduced the sensitivity of this group for detecting the presence of neoplasms. The incidences of adenomas or carcinomas (combined) of the preputial or clitoral glands were marginally increased in male or female rats that received 200 mg/kg 2-amino-5-nitrophenol (preputial gland: 3/50; 2/50; 5/50; clitoral gland: 3/50; 3/50; 7/50). Neoplasms found in the intestinal tract of 3/50 male rats that received 100 mg/kg (one leiomyoma of the small intestine, one adenocarcinoma of the jejunum, one leiomyoma of the cecum), 2/50 male rats that received 200 mg/kg (one lipoma and one osteosarcoma of the cecum), and 1/50 female rats that received 200 mg/kg (one leiomyoma of the cecum) were not considered to be the result of chemical exposure. No compound-related neoplasms were found in mice exposed to 2-amino-5-nitrophenol in the 2-year studies.

Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases.

2-Amino-5-nitrophenol's production and use as an intermediate in the manufacture azo dyes, which are used for coloring synthetic resins, lacquers, inks and wood stains and its use as a dye in semi-permanent hair coloring products and limited use in permanent hair coloring products(1) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 85(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrophenol is expected to have high mobility in soil(SRC). Volatilization of 2-amino-5-nitrophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Amino-5-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(4). Biodegradation data were not available(SRC, 2007).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 85(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrophenol is 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 7.8X10-13 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 0.99(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2007).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-amino-5-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 2-amino-5-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 41 hours(SRC), calculated from its rate constant of 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-amino-5-nitrophenol may be removed from the air by wet or dry deposition(SRC).

The rate constant for the vapor-phase reaction of 2-amino-5-nitrophenol with photochemically-produced hydroxyl radicals has been estimated as 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 41 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Amino-5-nitrophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-Amino-5-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 in fish for 2-amino-5-nitrophenol(SRC), using an estimated log Kow of 0.99(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-amino-5-nitrophenol can be estimated to be 85(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-amino-5-nitrophenol is expected to have high mobility in soil(SRC).

The Henry's Law constant for 2-amino-5-nitrophenol is estimated as 7.8X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-amino-5-nitrophenol is expected to be essentially nonvolatile from water surfaces(2). 2-Amino-5-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 14,512 workers (11,827 of these are female) are potentially exposed to 2-amino-5-nitrophenol in the US(1). Occupational exposure to 2-amino-5-nitrophenol may occur through dermal contact with this compound at workplaces where 2-amino-5-nitrophenol is produced or used(SRC). Use data indicates that the general population may be exposed to 2-amino-5-nitrophenol via dermal contact with consumer products containing 2-amino-5-nitrophenol(SRC).

The principal rat liver microsomal metabolite of 4-nitroaniline was isolated by high pressure liquid chromatography and was characterized as 2-amino-5-nitrophenol (2-hydroxy-4-nitroaniline) by comparison of its mass, nuclear magnetic resonance, and ultraviolet spectra and HPLC retention time to the synthetic compound. ... Pretreatment of rats with phenobarbital and 3-methylcholanthrene increased the rate of conversion of 4-nitroaniline to 2-hydroxy-4-nitroaniline by 2-fold and 4-fold, respectively; the reaction required NADPH and was inhibited by heat treatment of microsomes, by argon and carbon monoxide:oxygen atmospheres and by the cytochrome P-450 inhibitor, 2-[(2,4-dichloro-6-phenyl)phenoxy]ethylamine. ...

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (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)

2-amino-5-nitrophenol

2-Amino-5-nitrophenol is available commercially with the following specifications: purity, 98% (min); ash, 0.05% (max); iron, 40 ppm (max); lead, 5 ppm (max); arsenic, 2 ppm (max).

Phenol, 2-amino-5-nitro-: ACTIVE|2-Amino-5-nitrophenol is not produced in commercial quantities in the USA. It is available in research quantities, at purities ranging from 90-99% from Jos. H. Lowenstein & Sons, 1991; TCI America, 1991; Aldrich Chemical Co., 1992; Fluka Chemie AG, 1993.

Analyte: 2-amino-5-nitrophenol; matrix: chemical purity; procedure: thin-layer chromatography|Analyte: 2-amino-5-nitrophenol; matrix: chemical purity, stability; procedure: high-performance liquid chromatography with ultraviolet detection at 254 nm