4-Nitro-1,1'-biphenyl

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Nitros, Aromatic

SWEETISH ODOR

Sweetish odor.

YELLOW NEEDLES FROM ALC

WHITE NEEDLES

White to yellow, needle-like, crystalline solid.

Insoluble (NIOSH, 2024)

SOL IN ETHER, BENZENE, CHLOROFORM, ACETIC ACID

SLIGHTLY SOL IN COLD ALC

Solubility in water: very poor

Insoluble

290 °F (NIOSH, 2024)

290 °F

143 °C c.c.

290 °F

290 °F

644 °F at 760 mmHg (NIOSH, 2024)

340 °C @ 760 MM HG

340 °C

644 °F

340 °C @760 [mm Hg]

644 °F

237 °F (NIOSH, 2024)

114 °C

114 °C

237 °F

114 °C

237 °F

Danger

H350: May cause cancer [Danger Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Danger

H350 (100%): May cause cancer [Danger Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Carcinogenicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity; Ocular Toxicity; Respiratory Toxicity

Restricted substance: 4-Nitrobiphenyl

4-Nitrodiphenyl: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

4-Nitrobiphenyl is no longer manufactured or used in the United States. Limited information is available on the health effects of 4-nitrobiphenyl. Acute (short-term) exposure to 4-nitrobiphenyl in humans results in irritation of the eyes, mucous membranes, and respiratory tract, and headache, nausea, vomiting, and fatigue. Chronic (long-term) exposure to high concentrations of 4-nitrobiphenyl in workers has resulted in effects on the peripheral and central nervous systems and the liver and kidney. No information is available on the reproductive, developmental, or carcinogenic effects of 4-nitrobiphenyl in humans. EPA has not classified 4-nitrobiphenyl for carcinogenicity.

A metabolite of 4-nitrodiphenyl (4-aminodiphenyl) is a recognized bladder carcinogen. Therefore, 4-nitrodiphenyl is classified as a suspected human carcinogen, without an assigned TLV. [ACGIH]

Berlin A, Draper M et al; The toxicology of chemicals - 1. Carcinogenicity, Volume 1 - summary reviews of the scientific evidence. Office for Official Publications of the European Communities, L-2985 Luxembourg, 1989, Vol.1. 184p. Data reviewed includes, introduction, animal data, mutagenic and genotoxic information, human data, scientific conclusions, need for further work, references.

Fu PP; Metabolism of nitropolycyclic aromatic hydrocarbons. Drug Metab Rev 22 (2-3): 209-68 (1990). A review with 229 references on metabolism of nitro compounds.

Workers' exposure to 4-nitrobiphenyl is to be controlled through the required use of engineering controls, work practices, & personal protective equipment, incl respirators. Identified as an occupational carcinogen without establishing a PEL.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. p-Nitrobiphenyl is included on this list.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Use water spray.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Rinse mouth. Refer for medical attention .

Excerpt from NIOSH Pocket Guide for 4-Nitrobiphenyl:

(General first aid procedures)

RESEARCH PROGRAM WAS CONDUCTED TO DETERMINE THE CAPABILITY OF BIOL TREATMENT AND ACTIVATED CARBON ADSORPTION TO REMOVE CHEM CARCINOGENS FROM WATER AND WASTEWATER. CMPD STUDIED INCL 4-NITROBIPHENYL. ALL CMPD TESTED EXHIBITED SOME DEG OF BIOL DEGRADATION. CARBON ADSORPTION WAS ALSO EFFECTIVE IN REMOVING THE CMPD FROM AQ SOLN.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed or replaced.

The worker should wash daily at the end of each work shift.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

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.

TERRESTRIAL FATE: The important p-nitrobiphenyl degradation process in soil may be biodegradation. A single biodegradation study has shown that p-nitrobiphenyl is biodegradable with rapid microbial adaptation. Estimated Koc values of 2680-3360 indicate that significant leaching should not occur in most types of soil. Photodegradation on soil surfaces exposed to sunlight may be possible. (SRC)

AQUATIC FATE: The important p-nitrobiphenyl degradation processes in water may be biodegradation and photolysis. A single biodegradation study has shown that p-nitrobiphenyl is significantly biodegradable with rapid microbial adaptation. p-Nitrobiphenyl has also been shown to photodegrade rapidly when diethylamine solutions are exposed to uv light above 290 nm. Photolysis in water may be important; however, kinetic rate data pertaining to environmental photolysis are not available to predict its relative significance. Estimated Koc values of 2680-3360 indicate that some partitioning from the water column to sediments and suspended material may occur. Moderate bioconcentration may be possible. Aquatic volatilization is expected to be relatively slow in comparison to other fate processes. Aquatic hydrolysis is not expected to be important. (SRC)

ATMOSPHERIC FATE: Based upon its chemical structure, p-nitrobiphenyl is expected to exist primarily in the vapor-phase in the ambient atmosphere, although a small percentage may be associated with the particulate-phase. Vapor-phase p-nitrobiphenyl is degraded in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals. Degradation via direct photolysis may also be important; however, kinetic rate data pertaining to environmental photolysis are not available to predict its relative significance. (SRC)

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

inhalation, skin absorption, ingestion, skin and/or eye contact

See Effects of long-term or repeated exposure.

MAY BE ABSORBED!

Redness.

headache, drowsiness, dizziness; dyspnea (breathing difficulty); ataxia, lassitude (weakness, exhaustion); methemoglobinemia; urinary burning; acute hemorrhagic cystitis; [potential occupational carcinogen]

THERE ARE NO DATA ON CARCINOGENICITY OF 4-NITROBIPHENYL IN MAN. HOWEVER, IT HAS BEEN USED IN PRODN OF 4-AMINOBIPHENYL, WHICH IS RECOGNIZED HUMAN BLADDER CARCINOGEN.

SUMMARY TOXICITY STATEMENT: /ACUTE/ ... MODERATE VIA ORAL ROUTE. MODERATE= MAY CAUSE REVERSIBLE OR IRREVERSIBLE CHANGES ... /TO EXPOSED TISSUE/, NOT NECESSARILY SEVERE ENOUGH TO CAUSE SERIOUS PHYSICAL IMPAIRMENT OR THREATEN LIFE.

THE INTERNATIONAL AGENCY FOR RESEARCH ON CANCER WORKING GROUP ON THE EVALUATION OF THE CARCINOGENIC RISK OF CHEMICALS TO MAN FOUND NO REPORTS ON CARCINOGENICITY OF 4-NITROBIPHENYL TO MAN. THE GROUP CONCLUDED THAT IT IS NOT POSSIBLE TO SEPARATE THE EXPOSURES TO 4-NITROBIPHENYL FROM EXPOSURES TO 4-AMINOBIPHENYL BECAUSE THE FORMER IS CONVERTED TO THE LATTER BY REDUCTION.

No data are currently available to suggest that p-nitrobiphenyl is currently manufactured, imported, used or sold on a commercial-scale in the United States. No data are available to suggest that p-nitrobiphenyl is inadvertently formed during any commercial process or in the environment. (SRC)

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. p-Nitrobiphenyl is included on this list.

THE PROFILES OF BLADDER EPITHELIUM DNA ADDUCTS QUANTIFIED AT VARIOUS TIMES AFTER TREATMENT OF MALE BEAGLE DOGS WITH ARYLAMINES INCL 4-NITROBIPHENYL WERE REMARKABLY SIMILAR TO PROFILES OBTAINED WHEN THE N-HYDROXYARYLAMINE METABOLITES OF THESE CARCINOGENS WERE REACTED WITH DNA IN VITRO AT PH 5. INCUBATION OF N-HYDROXYARYLAMINES WITH SALMONELLA TYPHIMURIUM STRAINS AND DETERMINATION OF THE RESULTING DNA ADDUCTS AND REVERSIONS SUGGEST THAT THE HYDROXYARYLAMINES ARE ULTIMATE BLADDER CARCINOGENS AND C8-DEOXYGUANOSINE SUBSTITUTION MAY REPRESENT AN INITIATING LESION IN BLADDER TUMOR FORMATION.

4-NITROBIPHENYL YIELDS 4-NITROSOBIPHENYL IN CAT. /FROM TABLE/

... IN RATS 4-NITROBIPHENYL WAS CONVERTED TO 4-AMINOBIPHENYL & 4-AMINOBIPHENYL-3-YL HYDROGEN SULFATE. ... IN VITRO 25% OF 4-NITROBIPHENYL ... REDUCED TO 4-AMINOBIPHENYL WITHIN 40 MIN DURING ANAEROBIC REDN IN PRESENCE OF RAT LIVER ENZYMES & NECESSARY COFACTORS.

SMALL AMT OF NON-ACETYLATED N-HYDROXY PRODUCTS HAVE BEEN IDENTIFIED IN URINE OF DOGS & MONKEYS GIVEN SINGLE DOSE OF 5 MG/KG BODY WT 4-NITROBIPHENYL ... .

Nitro polycyclic aromatic hydrocarbons are metabolized in vitro to genotoxic agents by way of ring oxidation or nitroreduction. The metabolism of compounds such as 4-nitrobiphenyl, ... in mammalian cells is described. The exact metabolic pathways depend upon the particular compound, but in each case the nitro group appears to play a critical role in the activation process. In oxidative metabolism, the location of the nitro group influences the regioselectivity of ring oxidtaion. Reduction may involve activation to reactive N-hydroxy arylamines.

4-Nitrobiphenyl is no longer manufactured, imported, used, or sold in the United States.

Used as a plasticizer for resins and polystyrene, a fungicide for textiles, and a wood preservative; [ACGIH] Used in the production of 4-Aminobiphenyl, a confirmed bladder carcinogen; [IARC] Formerly used in the production of 4-Aminobiphenyl; [Merck Index]

See carcinogens in 29CFR1910.1003 (Code of Federal Regulations).

Applying Wood Preservatives [Category: Other]

Formerly in prepn of p-biphenylamine.

1,1'-Biphenyl, 4-nitro-: ACTIVE

AS PLASTICIZER FOR RESINS, POLYSTYRENES, CELLULOSE ACETATE AND NITRATE, AS A FUNGICIDE FOR TEXTILES AND AS A PRESERVATIVE FOR WOOD.

PRESENCE, USE & MFR OF 4-NITROBIPHENYL IN FACTORIES IS PROHIBITED IN UK UNDER CARCINOGENIC SUBSTANCES REGULATIONS 1967- STATUTORY INSTRUMENT (1967), NUMBER 487. IT IS ALSO LISTED WITH 13 OTHER CMPD IN US FEDERAL REGISTER (USA GOVERNMENT, 1973) AS SUBJECT TO EMERGENCY TEMPORARY STD ON CERTAIN CARCINOGENS UNDER ORDER MADE BY OCCUPATIONAL SAFETY & HEALTH ADMIN, DEPT OF LABOR, ON 26 APRIL, 1973.