N-Phenyl-p-phenylenediamine

184.24

184.24

908935

202-951-9

007X4XXS71

1446

37074|3401

1673

DTXSID7025895

Needles (alcohol)|Purple powder|Purple needles

29215990

38

2.4 (calculated)

Clear Liquid

1.09 g/cm³

75 °C

354 °C

193°C

1.6266 (estimate)

soluble in water at 20°C 0.6g/L. soluble in ethanol.ethanol: soluble 10mg/mL, clear, very dark red (Violet to brown to black solution)

Store below +30°C.

Vapour pressure, Pa at 20°C: 0.000076

Oral-rat LD50: 464 mg/kg; Oral-Mouse LD50: 464 mg/kg

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

Henry's Law constant = 3.7X10-10 atm-cu m/mol at 25 °C (est)

pKa = 5.20 (conjugate acid)

Heat of formation = 2.06X10+8 J/kmol; liquid molar volume = 0.188 cu m/kmol|Hydroxyl radical reaction rate constant = 2.0X10-10 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Amines, Aromatic

N-PHENYL-P-PHENYLENEDIAMINE is incompatible with strong oxidizers. It is also incompatible with strong acids. It may react with plastics. (NTP, 1992)

-6.29X10+9 J/kmol

9.26X10+7 J/kmol at 25 °C

Critical temperature: 867 K; critical pressure: 3.19X10+6 Pa

III

9

UN3077

3

22-36-43-42/43-36/37/38-20/22-50/53

26-36-45-36/37/39-61-60-36/37

ST3150000

Xn,Xi,N

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

Irritant

Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, plastics.

P273-P280-P305 + P351 + P338-P501

H302-H317-H319-H410

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.

Bioassay of p-Aminodiphenylamine for Possible Carcinogenicity (1978) Technical Rpt Series No. 82 DHEW Pub No. (NIH) 78-1332, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014[Available from, as of April 4, 2003: http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr082.pdf]|European Commission, ESIS; IUCLID Dataset, p-aminodiphenylamine (101-54-2) (2000 CD-ROM edition).[Available from, as of March 1, 2009: http://esis.jrc.ec.europa.eu/]

This chemical is combustible. (NTP, 1992)|Combustible.

|Warning|H302 (96.66%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, P391, and P501|Aggregated GHS information provided by 569 companies from 17 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|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P309+P311, P321, P330, P333+P313, P337+P313, P363, P405, 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 dry powder, carbon dioxide.

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: 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 store this chemical at ambient temperatures, and keep it away from oxidizing materials and acids. (NTP, 1992)

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)

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.

Separated from strong oxidants and strong acids. Dry.

A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance is irritating to the skin and eyes. Ingestion could cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

PREVENT DISPERSION OF DUST! AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective clothing. Protective gloves.

Wear safety spectacles or eye protection in combination with breathing protection if powder.

highly toxic

LD50 Mouse oral 244 mg/kg|LD50 Rat Oral 720 mg/kg bw|LD50 Rabbit Dermal >5000 mg/kg bw|LD50 Rat oral 847 mg/kg bw

A bioassay of N-phenyl-p-phenylenediamine for possible carcinogenicity was conducted by administering the test chemical in the diet to Fischer 344 rats and B6C3F1 mice. Groups of 50 rats of each sex were administered /the test cmpd/ at one of two doses, either 600 or 1,200 ppm, for 78 wk and were then observed for an additional 26 wk. Matched controls consisted of groups of 20 untreated rats of each sex. All surviving rats were /sacrificed/ at 104 wk. Groups of 50 mice of each sex were initially administered /the test cmpd/ at one of the following doses, either 2,500 or 5,000 ppm for the males and either 5,000 or 10,000 ppm for the females, for 31 wk. Because of toxicity ... the doses were lowered at that time and terminated at 48 wk. The animals were then observed for 43 additional wk. Time weighted avg doses during the period of administration were 2,057 or 4,114 ppm for the males and 3,672 or 8,170 ppm for the females. Matched controls consisted of groups of 20 untreated mice of each sex. All surviving mice were /sacrificed/ at 91 wk. ... Under the conditions of this bioassay, N-phenyl-p-phenylenediamine was not carcinogenic for Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

p-Aminodiphenylamine's production and use as a dye intermediate(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 3.1X10+3(SRC), determined from a structure estimation method(2), indicates that p-aminodiphenylamine is expected to have slight mobility in soil(SRC). The pKa of p-aminodiphenylamine is 5.20(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of p-aminodiphenylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.7X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(5). p-Aminodiphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.21X10-5 mm Hg at 25 °C(6). Reported inherent biodegradation values of 28% after 20 days in an adapted activated sludge and 58% after 3 hours in a mixed, non-adapted activated sludge inoculum(7) suggest that biodegradation in the aquatic environment may be an important fate process(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.1X10+3(SRC), determined from a structure estimation method(2), indicates that p-aminodiphenylamine 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 3.7X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A pKa of 5.20(5) indicates p-aminodiphenylamine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(6). According to a classification scheme(7), an estimated BCF of 5.1(SRC), from an estimated log Kow of 1.82(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low. Reported inherent biodegradation values of 28% after 20 days in an adapted activated sludge and 58% after 3 hours in a mixed, non-adapted activated sludge inoculum(10) suggest that biodegradation in the aquatic environment may be an important fate process(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-aminodiphenylamine, which has a vapor pressure of 1.21X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase p-aminodiphenylamine 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 1.9 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). Particulate-phase p-aminodiphenylamine may be removed from the air by wet or dry deposition(SRC). p-Aminodiphenylamine 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 p-aminodiphenylamine 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 1.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). p-Aminodiphenylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). p-Aminodiphenylamine contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 5.1 was calculated for p-aminodiphenylamine(SRC), using an estimated log Kow of 1.82(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 p-aminodiphenylamine can be estimated to be 3.1X10+3(SRC). According to a classification scheme(2), this estimated Koc value suggests that p-aminodiphenylamine is expected to have slight mobility in soil. The pKa of p-aminodiphenylamine is 5.20(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

The Henry's Law constant for p-aminodiphenylamine is estimated as 3.7X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that p-aminodiphenylamine is expected to be essentially nonvolatile from water surfaces(2). A pKa of 5.20(2) indicates p-aminodiphenylamine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces or moist soil is not expected to be an important fate process(3). p-Aminodiphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.21X10-5 mm Hg(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,356 workers (530 of these were female) were potentially exposed to p-aminodiphenylamine in the US(1). Occupational exposure to p-aminodiphenylamine may occur through inhalation of dust and dermal contact with this compound at workplaces where p-aminodiphenylamine is produced or used. The general population may be exposed to p-aminodiphenylamine via dermal contact with consumer products containing p-aminodiphenylamine(SRC).

4(?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).

Aminodiphenylamine binds to the proteins of the intestinal mucosa.|Skin segments (1 sq cm) of male albino rats without underlying connective tissue and subcutaneous fat were used for uptake and efflux studies. 4-ADPA binds to skin showing saturation kinetics with Km= 2.54 X10 (-4) and Vmax= 4.76 micromol/g skin. Uptake dependent upon area of skin, concentration, exposure time, temperature and pH of the vehicle. No effects of bioinhibitors, suggesting a non-energy dependent process. Skin bound to 4-ADPA was effluxed through serum proteins.|P-aminodiphenylamine (p-ADPA) binds liver proteins. Aspartic and glutamic acids are presumably the responsible units in the protein chain involved in this binding with p-ADPA. p-ADPA is changed into a quinone structure after atmospheric oxidation in Krebs-ringer-bicarbonate buffer, pH 7.4, in the presence of trace metal ions. This oxidized form of p-ADPA binds with aspartic acid at pH 7.4 and temp 40 deg in 2 hr.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes and upper respiratory tract. It may also cause irritation of the skin and mucous membranes. Other symptoms include headache, dizziness and methemoglobinemia with symptoms of cyanosis including bluish discoloration of the lips, earlobes and fingernails. Dermatitis has been reported. ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It is also harmful by inhalation 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. 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. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)

Fresh air, rest. Refer for medical attention.

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.

TREATMENT IS SYMPTOMATIC. WHENEVER HISTAMINE-LIKE EFFECTS PREDOMINATE, THERAPEUTIC TRIAL WITH AN ANTIHISTAMINIC IS SUGGESTED. /PRC: POTENTIAL METHEMOGLOBIN FORMER./ /PHENYLENEDIAMINE/|METHYLENE BLUE, ALONE OR IN COMBINATION WITH OXYGEN, IS INDICATED AS TREATMENT IN METHEMOGLOBINEMIIA.|/SRP:/ 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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Organic bases/Amines and related compounds/|/SRP:/ 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/|/SRP:/ 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. DIRECT PHYSICIAN ORDER ONLY ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

/HUMAN EXPOSURE STUDIES/ A study of contact dermatitis in Italian hairdressers was conducted in a cohort of 302 hairdressers (43 men and 259 women, mean age 24.6 years) who were treated for skin problems at Italian dermatology clinics over a 5 year period. Of these, 184 were patch tested with an Italian standard allergen series and a hairdresser's allergen series. ... The subjects had been employed as hairdressers a mean of 5.3 years. ... Among hair dye allergens, p-phenylenediamine, para-aminodiphenylamine, o-nitro-p-phenylenediamine, and para-toluenediamine caused a high incidence of positive reactions, 24.2, 10.6, 7.9, and 13.2%, respectively. ... It was concluded that a high proportion of hairdressers who seek treatment for skin problems have allergic contact dermatitis.|/HUMAN EXPOSURE STUDIES/ A cleaner at a chemical plant suffering from allergic skin reaction of the face, neck and arms was tested. Positive reaction to 0 25% test substance in petrolatum after 48 and 72 hr.|/HUMAN EXPOSURE STUDIES/ Cosmetic intolerance has been studied in 5202 patients; tested for possible contact dermatitis. Results: 107 (2.1%) showed positive reaction to the test substance; from 156 patients with pure allergy to cosmetics 5 (3.2%) -reacted positve to the test substance.|/HUMAN EXPOSURE STUDIES/ Tests were performed in 181 persons with confirmed group sensitization to aromatic amino compounds; test concentration 1% of the test substance; results: 96 patients (53%) showed positive reaction.|For more Human Toxicity Excerpts (Complete) data for P-AMINODIPHENYLAMINE (8 total), please visit the HSDB record page.

4-aminodiphenylamine

The substance can be absorbed into the body by inhalation and by ingestion.

Redness. Pain.

Redness. Pain.

HAIR DYES ARE PREPARED BY COMBINING 2,6-DIAMINOPYRIDINE OR ITS SALT, P-AMINODIPHENYLAMINE OR ITS SALT, AND 2,5-DIAMINOPYRIDINE OR ITS SALT AT THE MOLE RATIO OF 1:2:3.

All other basic organic chemical manufacturing|1,4-Benzenediamine, N1-phenyl-: ACTIVE

ION-EXCHANGE TLC SEPARATION AND IDENTIFICATION OF COLORING AGENTS IN OXIDATION-TYPE HAIR DYES.|IDENTIFICATION AND ESTIMATION OF OXIDATION-TYPE HAIR DYES BY HPLC.

Cosmetics -> Hair dyeing