Nitro-p-phenylenediamine

153.14

153.14

226-164-5

PV83F3C01Q

1542

5377

1673

DTXSID4020957

Almost black needles with dark-green luster

29215119

97.9

0.5

Brown to black Powder

1.4±0.1 g/cm3

137 °C

276.04°C (rough estimate)

186.9±22.3 °C

1.708

H2O: <0.1 g/100 mL at 22 ºC

Store below +30°C.

5.60X10-5 mm Hg at 25 deg C (est)

Oral-rat LD50: 2100  mg/kg; Celiac-ratLD50: 348 mg/kg

Flammable; burning produces toxic nitrogen oxide fumes

Henry's Law constant = 5.81X10-11 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 2.20X10-11 cu cm/molec-sec at 25 °C (est)

This chemical may be sensitive to prolonged exposure to light and air. Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

2-NITRO-P-PHENYLENEDIAMINE is incompatible with strong oxidizing agents. (NTP, 1992)

I; II; III

6.1

3143

2

43-68

36/37-45

ST3000000

Xi,Xn

Warehouse ventilated, low temperature and dry

Stable. Incompatible with strong oxidizing agents.

P280

H317

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.

2-Nitro-p-phenylenediamine. a component of both semipermanent and permanent hair dye formulations, was selected for bioassay by the National Cancer Institute because of the increased incidence of bladder cancer among dye manufacturing industry workers. Aromatic amines are one of several classes of organic chemicals thought to contribute to the increased cancer risk in this industry. The widespread exposure to 2-nitro-p-phenylenediamine among the general population, and the possibility of an increased cancer risk among hairdressers were additional factors in the selection of this compound for testing. A bioassay for the possible carcinogenicity of 2-nitro-p-phenylenediamine was conducted using Fischer 344 rats and B6C3F1 mice. ... Under the conditions of this bioassay, dietary administration of 2-nitro-p-phenylenediamine was carcinogenic to female B6C3F1 mice, causing an increased incidence of hepatocellular neoplasms, primarily hepatocellular adenomas. There was no convincing evidence for the carcinogenicity of the compound in Fischer 344 rats or in male B6C3F1 mice.[DHEW/NCI; Bioassay of 2-Nitro-p-phenylenediamine for Possible Carcinogenicity (1979) Technical Rpt Series No. 169 DHEW Pub No. (NIH) 79-1725]|A safety assessment of 2-nitro-p-phenylenediamine and 4-nitro-o-phenylenediamine was published in 1985 with the conclusion "for those persons not sensitized, the Expert Panel Concludes that 2-nitro-p-phenylenediamine and 4-nitro-o-phenylenediamine are safe as hair dye ingredients at the current concentration of use" ... Studies available since that safety assessment was completed, along with updated information regarding uses and use concentrations, were considered by the CIR Expert Panel. The Panel determined to not reopen this safety assessment.[Cosmetic Ingredient Review; 2-Nitro-p-Phenylenediamine and 4-Nitro-o-Phenylenediamine. JACT 4(3): 161-202, 1985; Re-Review: International Journal of Toxicology. 25(S2), 2006]

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H315 (17.81%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 74 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, 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)|Use water spray, powder.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment.

Separated from strong oxidants.

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.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

See EFFECTS OF LONG-TERM OR REPEATED EXPOSURE. PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles.

moderately toxic

LD50 Rat oral (M & F) 1800 mg/kg|LD50 Rat (Charles River CD) oral 3080 mg/kg bw /oil-in-water emulsion/|LD50 Rat ip 348 mg/kg bw /compound in dimethylsulfoxide/|LD50 Rat (Wistar male) oral 2100 mg/kg bw

A bioassay for the possible carcinogenicity of 2-nitro-p-phenylenediamine was conducted using Fischer 344 rats and B6C3F1 mice. 2-Nitro-p-phenylenediamine was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each species. Twenty animals of each sex and species were placed on test as controls. The high and low dietary concentrations of 2-nitro-p-phenylenediamine were, respectively, 1,100 and 550 ppm for male rats, 2,200 and 1,100 ppm for female rats, and 4,400 and 2,200 ppm for mice of both sexes. The compound was administered in the diet for 78 weeks, followed by an observation period of 27 weeks for rats and 12 to 13 weeks for mice. There were no significant positive associations between the dietary concentrations of 2-nitro-p-phenylenediamine administered and mortality in rats and mice of either sex. Adequate numbers of animals in all groups survived sufficiently long to be at risk from late-developing tumors. Mean body weight depression, relative to controls, was observed in dosed rats and mice of both sexes, indicating that the concentrations administered to these animals may have approximated the maximum tolerated dosages. When the female mice in each group, having hepatocellular carcinoma or hepatocellular adenoma, were combined and the resulting incidences statistically analyzed, there was a significant positive association between concentration administered and the incidence of these tumors. This finding was supported by a significant high dose to control Fisher exact comparison. No tumors occurred in statistically significant increased incidences when dosed male or female rats or male mice were compared to their respective controls. Under the conditions of this bioassay, dietary administration of 2-nitro-p-phenylenediamine was carcinogenic to female B6C3F1 mice, causing an increased incidence of hepatocellular neoplasms, primarily hepatocellular adenomas. There was no convincing evidence for the carcinogenicity of the compound in Fischer 344 rats or in male B6C3F1 mice.

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.

...is not known to occur as natural product.

2-Nitro-p-phenylenediamine's production and subsequent use in the production of dyes for semi-permanant and permanant hair coloring and dyeing of fur(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from a log Kow of 0.53(2) and a regression-derived equation(3), indicates that 2-nitro-p-phenylenediamine is expected to have very high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 2-nitro-p-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2-Nitro-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.6X10-5 mm Hg(SRC), determined from a fragment constant method(6). Information is not available regarding the biodegradation potential of 2-nitro-p-phenylenediamine; however, 80% percent of p-phenylenediamine was removed over 120 hours based on chemical oxygen demand measurements and using an activated sludge inoculum(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from a log Kow of 0.53(2) and a regression-derived equation(3), indicates that 2-nitro-p-phenylenediamine is not expected to adsorb to suspended solids and sediment(SRC). 2-Nitro-p-phenylenediamine may bind strongly to organic matter as aromatic amines are highly reactive with an affinity for organic materials(4). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.8X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-Nitro-p-phenylenediamine absorbs at a wavelength of 441 nm(8) and therefore may be susceptible to direct photolysis by sunlight(SRC). Information is not available regarding the biodegradation potential of 2-nitro-p-phenylenediamine; however, 80% percent of p-phenylenediamine was removed over 120 hours based on chemical oxygen demand measurements and using an activated sludge inoculum(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-nitro-p-phenylenediamine, which has an estimated vapor pressure of 5.6X10-5 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-nitro-p-phenylenediamine 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 17 hours(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-nitro-p-phenylenediamine may be removed from the air by wet or dry deposition(SRC). 2-Nitro-p-phenylenediamine absorbs at wavelengths of 441 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2-nitro-p-phenylenediamine with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Nitro-p-phenylenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-Nitro-p-phenylenediamine absorbs at wavelength of 441 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for 2-nitro-p-phenylenediamine(SRC), using a log Kow of 0.53(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 2-nitro-p-phenylenediamine is estimated as 46(SRC), using a log Kow of 0.53(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-nitro-p-phenylenediamine is expected to have very high mobility in soil. However, 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(4), suggesting that mobility may be much lower in some soils(SRC).

The Henry's Law constant for 2-nitro-p-phenylenediamine is estimated as 5.8X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-nitro-p-phenylenediamine is expected to be essentially nonvolatile from water surfaces(2). 2-Nitro-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.6X10-5 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 29,422 workers (23,551 of these are female) are potentially exposed to 2-nitro-p-phenylenediamine in the US(1). Occupational exposure to 2-nitro-p-phenylenediamine may occur through dermal contact with this compound at workplaces where 2-nitro-p-phenylenediamine is produced or used. The general population is exposed to 4-nitro-1,2-diaminobenzene when using semi-permanent and permanent hair color products containing 4-nitro-1,2-diaminobenzene(2).|Direct skin contact is probably the major route of absorption of the aromatic amines(1).

/In an/ ... experiment conducted with groups of 2 to 3 rats, each rat was treated with 200 uL of 50 % hair colorant base containing 0.025 to 0.48 % /2-nitro-p-phenylenediamine/ (2NPPD) (14C) on 10 sq cm of skin for five minutes. The base was rinsed off, and a 48-hour nonocclusive patch was applied. Skin penetration increased with increasing 2NPPD concentration and was proportional to 2NPPD concentration; it was 0.01 ug/sq cm with 0.025 % 2NPPD and 3.2% with 0.48 % 2NPPD.|Pairs of male and female rats were intubated or injected intraperitoneally with 0.5 mL of /2-nitro-p-phenylenediamine/ (2NPPD) (14C) in 5 percent Tween 80. Expired air was assayed for radioactivity for 24 hours, and urine and feces were assayed. No radioactivity was in expired air. At 3 days, 1 to 2 percent of the applied radioactivity was in the carcass. The rate of excretion was rapid; 85 to 90 percent of the applied radioactivity was recovered in the urine and the feces within 24 hours. Over 3 days, 48 to 68 percent was recovered in the feces and 27 to 41 percent in the urine. There were six metabolites and a trace of unchanged 2NPPD in the urine; the metabolites were acetylated 2NPPD, sulfite and/or glucuronide conjugates of 2NPPD and of acetylated 2NPPD, and two conjugates with sulfur-containing amino acids. Similar metabolites were found in the feces.|/2-nitro-p-phenylenediamine/ (2NPPD) (14C) was administered intraperitoneally in a dose of 2.6 mg/kg to rats ... and excretion was monitored. Within 24 hours, almost 92 percent of the radioactivity was excreted; 37.4 percent was in the urine and 54.3 percent was in the feces. After 4 days, 96 percent of the radioactivity had been excreted. ...|... In vitro studies /were conducted/ to measure absorption and metabolism of 2-nitro-p-phenylenediamine (2NPPD) in human and fuzzy rat skin and rat jejunal tissue. ... In human skin, the percentages of total applied dose absorbed (receptor fluid + skin) over 24 hr were 9.2 +/- 5.7 (mean +/- SD) and 9.5 +/- 3.2 for ... ethanol and semipermanent /hair dye/ vehicles, respectively, with approximately 3% remaining in skin. In rat skin, the percentages of total applied dose absorbed over 24 hr were 9.3 +/- 1.2 (mean +/- SE), 6.9 +/- 1.2, and 4.2 +/- 0.1 for the ethanol, semipermanent, and permanent formulation vehicles, respectively, with approximately 3% remaining in skin. In rat intestinal tissue, the percentage of total applied dose absorbed over 24 hr was 10.9 +/- 1.2, with approximately 5% remaining in the tissue. ...

Pairs of male and female rats were intubated or injected intraperitoneally with 0.5 mL of /2-nitro-p-phenylenediamine/ (2NPPD) (14C) in 5 percent Tween 80. ... There were six metabolites and a trace of unchanged 2NPPD in the urine; the metabolites were acetylated 2NPPD, sulfite and/or glucuronide conjugates of 2NPPD and of acetylated 2NPPD, and two conjugates with sulfur-containing amino acids. Similar metabolites were found in the feces.|... In human and rat skin, 2-nitro-p-phenylenediamine (2NPPD) was metabolized to triaminobenzene and N4-acetyl-2NPPD. 2NPPD was also metabolized to a sulfated 2NPPD metabolite in rat skin, but not in human skin. 2NPPD was extensively metabolized in both human and rat skin with ethanol application; metabolism was not as extensive with a semipermanent /hair dye/ formulation application. In rat intestinal tissue, 62% of 2NPPD was metabolized upon absorption to triaminobenzene and N4-acetyl-2NPPD. Differences in the metabolic profiles (proportion of each metabolite formed) were found between the skin and intestinal tissue. These results suggest that 2NPPD is rapidly absorbed and extensively metabolized in both skin and intestinal tissue. The extent of metabolism and the metabolic profile were found to be species-, tissue-, and dosing vehicle-dependent. ...

AVAIL IN JAPAN WITH MIN PURITY OF 99% & CONTAINS NITROAMINOACETANILIDE ISOMERS AS IMPURITIES.|2-Nitro-p-phenylenediamine is available commercially in purities ranging from 95 to 100%, with 4-amino-3-nitroacetanilide as a possible impurity.

SYMPTOMS: Symptoms of exposure to this compound may include irritation. ACUTE/CHRONIC HAZARDS: This compound may be harmful by ingestion and inhalation. It may cause irritation. 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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure 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)

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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

/HUMAN EXPOSURE STUDIES/ Thirty-nine hairdressers were patch tested for 24 hours with 2-nitro-p-phenylenediamine (2NPPD). Thirty-two of the hairdressers had no history of allergic contact dermatitis from p-phenylenediamine, and none of these 32 had a positive reaction to 2NPPD. One of seven hairdressers who had experienced strongly positive reactions to p-phenylenediamine was positive for 2NPPD. The researchers suggested that this may have been a cross reaction.|/CASE REPORTS/ A case has been described in the literature in which a dental hygienist developed dermatitis on the skin of her left forearm where it came into frequent contact with the hair of patients. A patch test with p-phenylenediamine mix was negative at 48 and 96 hours, and, with 2% 2-nitro-p-phenylenediamine, was strongly positive at 48 hours.|/GENOTOXICITY/ At 50-100 ug/mL, 2-nitro-p-phenylenediamine induced chromosome & chromatid gaps & breaks in human peripheral blood lymphocytes.|/GENOTOXICITY/ 2-Nitro-p-phenylenediamie... was active in inducing unscheduled DNA synthesis in HELA human cervical cancer cells.|For more Human Toxicity Excerpts (Complete) data for 2-NITRO-P-PHENYLENEDIAMINE (6 total), please visit the HSDB record page.

1,4-diamino-2-nitrobenzene

The substance can be absorbed into the body through the skin.

...AVAIL IN US AS COMMERCIAL GRADE WITH FOLLOWING TYPICAL SPECIFICATIONS: ASSAY, 97% MIN; MELTING RANGE, 135-138 °C; LOSS ON DRYING, 1.0% MAX; IRON CONTENT, 100 MG/KG MAX; RESIDUE ON IGNITION, 0.3%.|2-Nitro-p-phenylenediamine is available commercially in purities ranging from 95 to 100%, with 4-amino-3-nitroacetanilide as a possible impurity.|2-Nitro-p-phenylenediamine has the following specifications: ash, 0.1% (max); iron, 40 ppm (max); lead, 5 ppm (max); and arsenic, 2ppm(max).|IT HAS BEEN USED IN /HAIR DYES/ DARK-BROWN (@ LEVELS OF 0.1%), MEDIUM-BROWN (0.15%), MEDIUM-RED (2.5%) & ASH-BLOND (0.065%) DYE FORMULATIONS. IT CAN ALSO BE USED IN BLEACH-TONER FORMULATIONS FOR GOLDEN-BLOND (0.008%) & RED-BLOND (0.02%) SHADES.

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

SILICA GEL G PLATES HAVE BEEN USED TO SEPARATE & IDENTIFY MIXTURE OF BASIC DYES, INCLUDING 1,4-DIAMINO-2-NITROBENZENE... MIXTURE OF AROMATIC AMINES & AMINOPHENOLS...WAS DETERMINED SPECTROPHOTOMETRICALLY AFTER ELUTION FROM PLATES.

Cosmetics -> Hair dyeing