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Home > Encyclopedia > 4-Nitrosodiphenylamine

4-Nitrosodiphenylamine

4-Nitrosodiphenylamine structure

4-Nitrosodiphenylamine 

structure
  • CAS No:

    156-10-5

  • Formula:

    C12H10N2O

  • Chemical Name:

    4-Nitrosodiphenylamine

  • Synonyms:

    Benzenamine,4-nitroso-N-phenyl-;Diphenylamine,4-nitroso-;4-Nitroso-N-phenylbenzenamine;p-Nitrosodiphenylamine;p-Nitroso-N-phenylaniline;4-Nitrosodiphenylamine;N-Phenyl-p-nitrosoaniline;4-Nitroso-N-phenylaniline;p-Phenylaminonitrosobenzene;N-Phenyl-4-nitrosoaniline;NSC 5041;(4-Nitroso-phenyl)-phenyl-amine

Description

dark blue to black powder TKB is a black powder or a green plate-like material with a bluish luster.Green plates with bluish luster or a black powder.


P-nitrosodiphenylamine appears as green plates with bluish luster or a black powder. (NTP, 1992)


P-nitrosodiphenylamine appears as green plates with bluish luster or a black powder. (NTP, 1992)|Para-Nitrosodiphenylamine is a member of benzenes.

4-Nitrosodiphenylamine Basic Attributes

198.225

198.22

205-848-7

F7052989CV

5041

2811

DTXSID1021031

GREEN PLATES WITH BLUISH LUSTER (FROM BENZENE) OR STEEL-BLUE PRISMS OR PLATES (FROM ETHER + WATER)|YELLOW LIQUID PLATES|Greenish crystals

29214200

Characteristics

41.5

3.90110

P-nitrosodiphenylamine appears as green plates with bluish luster or a black powder. (NTP, 1992)

1.1447 (rough estimate)

144-145 °C

292 °C

169.5ºC

1.6330 (estimate)

SLIGHTLY SOL IN WATER OR PETROLEUM ETHER; FREELY SOL IN ALCOHOL, ETHER, CHLOROFORM, BENZENE

2.86E-05mmHg at 25°C

LD50 intravenous in mouse: 178mg/kg

UNDERGOES REDUCTION, ALKYLATION AND NITROSATION; FORMS SALTS WITH STRONG ACIDS AND BASES; THE BASIC SALTS REARRANGE TO A QUINOID STRUCTURE.

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

P-NITROSODIPHENYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. May react with strong oxidizing agents (NTP, 1992).

Safety Information

III

6.1(b)

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.2811

3

R22:Harmful if swallowed. R36/38:Irritating to eyes and skin .

26-36/37

JK0175000

Xn

AN UNUSUALLY STABLE NITROSO COMPOUND

P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501

H302

DHEW/NCI; Bioassay of p-Nitrosodiphenylamine for Possible Carcinogenicity (1979) Technical Rpt Series No. 190 DHEW Pub No. (NIH) 79-1746|National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 4-Nitrosodiphenylamine (156-10-5) is delisted as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/append/appb.pdf]

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

Fires involving this chemical should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (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: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene 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 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)|Wear nitrile rubber gloves, protective laboratory coat, self-contained breathing apparatus, eye protection and protective shoes. /Nitrosamines/

Toxicity

A bioassay for the possible carcinogenicity of p-nitrosodiphenylamine was conducted using Fischer 344 rats and B6C3F1 mice. p-Nitrosodiphenylamine was administered in the feed ... /to/ 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 p-nitrosodiphenylamine were, respectively, 5000 and 2500 ppm for rats. The high and low time-weighted average concentrations for mice were 9000 and 4254 ppm, respectively. The compound was administered for 78 weeks to rats, for 50 weeks to high dose mice and for 57 weeks to low dose mice. The period of compound administration was followed by an observation period of 27 weeks for rats and 35 weeks for mice. There were significant positive associations between the concentrations of p-nitrosodiphenylamine administered and mortality among male and female mice, but not for rats of either sex. ... Under the conditions of this bioassay, p-nitrosodiphylamine was carcinogenic when administered in the diet to male B6C3F1 mice, causing hepatocellular carcinomas. The chemical was also carcinogenic in male Fischer 344 rats, causing liver neoplasms. No evidence was provided for the carcinogenicity of p-nitrosodiphenylamine in female B6C3F1 mice or in female Fischer 344 rats.

PARA-NITROSODIPHENYLAMINE HAS BEEN PRODUCED COMMERCIALLY SINCE AT LEAST 1970. ITS USE AS A CHEMICAL INTERMEDIATE COULD RESULT IN OCCUPATIONAL EXPOSURE.

Drug Information

THE INTESTINES OF RATS TREATED IP WITH 1 G N-NITROSODIPHENYLAMINE WERE STAINED AND DILATED AFTER 24 HOURS. N-NITROSODIPHENYLAMINE WAS RAPIDLY REMOVED FROM THE LIVER AND KIDNEY WITH DIPHENYLAMINE AS AN IMPORTANT DEGRADATION PRODUCT. /N-NITROSODIPHENYLAMINE/

SYMPTOMS: Symptoms of exposure to this compound include skin and eye irritation. ACUTE/CHRONIC HAZARDS: This compound is highly toxic if inhaled, swallowed or absorbed through the skin. It is also an irritant. When heated to decomposition this compound emits toxic fumes. (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. 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)

4-nitroso-N-phenylaniline

4-Nitrosodiphenylamine Use and Manufacturing

Methods of Manufacturing

PROBABLY BY REACTION OF AN ALKYL ETHER OF 4-NITROSOPHENOL WITH ANILINE.|PARA-NITROSODIPHENYLAMINE CAN BE PREPARED BY THE FISCHER-HEPP REARRANGEMENT OF N-NITROSODIPHENYLAMINE; THIS IS BELIEVED TO BE THE METHOD USED FOR ITS COMMERCIAL PRODUCTION.

Uses

Has been used as retardant in vulcanizing rubber.

Production

(1975) PROBABLY GREATER THAN 9.08X10+5 G|(1977) PROBABLY GREATER THAN 9.08X10+5 G

ESSENTIALLY 100% AS ACCELERATOR FOR RUBBER VULCANIZATION

PARA-NITROSODIPHENYLAMINE IS AVAILABLE IN THE USA AS A PURPLE SOLID, TYPICALLY CONTAINING 95% ACTIVE INGREDIENT, 0.25% ASH, AND WITH A MELTING RANGE OF 140 TO 145 °C.

Benzenamine, 4-nitroso-N-phenyl-: ACTIVE|USE OF PARA-NITROSODIPHENYLAMINE AS A CHEMICAL INTERMEDIATE IS BELIEVED TO BE LIMITED PRIMARILY TO THE PRODUCTION OF N-PHENYL-PARA-PHENYLENEDIAMINE AND ITS DERIVATIVES. THIS DIAMINE SERVES AS AN AZOIC DIAZO COMPONENT, AS AN OXIDATION BASE, AS A DEVELOPER OF DIAZOTIZED DIRECT DYES, AND AS AN INTERMEDIATE IN THE MANUFACTURE OF OTHER DYES. IT IS ALSO BELIEVED TO BE USED AS AN ANTIOXIDANT IN RUBBER AND AS AN INTERMEDIATE IN THE SYNTHESIS OF OTHER ANTIOXIDANTS.

COLORIMETRIC DETERMINATION OF P-NITROSODIPHENYLAMINE IN WASTE WATER.|HIGH PERFORMANCE LIQUID CHROMATOGRAPHY METHOD IS USED FOR ANALYSIS OF PARA-NITROSODIPHENYLAMINE IN AMINE MIXTURES; ... HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY OF COMPOUNDS OBTAINED DURING THE PRODUCTION OF N-NITROSODIPHENYLAMINE.

Computed Properties

Molecular Weight:198.22
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:198.079312947
Monoisotopic Mass:198.079312947
Topological Polar Surface Area:41.5
Heavy Atom Count:15
Complexity:194
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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