4-Nitro-1,1′-biphenyl

199.21

199.21

202-204-7

QM80NUW6WZ

1395

1324

2811

DTXSID9041522

YELLOW NEEDLES FROM ALC|WHITE NEEDLES|White to yellow, needle-like, crystalline solid.

2904209020

45.8

3.77

White Solid

1.2±0.1 g/cm3

114 °C

340 °C @ Press: 760 Torr

43 °C

1.605

Insoluble

Oral-Rat  LD50: 2230 mg/kg; Abdominal cavity-mouse  LD50: 347 mg/kg

Combustible; Fire breaks down toxic nitrogen oxide fumes

SWEETISH ODOR

UV: 373 (Sadtler Research Laboratories Spectral Collection) /Biphenyl, 2-nitro/|UV: 6834 (Sadtler Research Laboratories Spectral Collection) /Biphenyl, 3-nitro/

Insoluble in water.

Hydrocarbons, Aromatic

4-NITROBIPHENYL is incompatible with the following: Strong reducers (NIOSH, 2016).

Combustible Solid

III

6.1(b)

2811

45-51/53

53-45-61

DV5600000

T,N

Storeroom low temperature, ventilated, dry; fireproof; stored separately from strong oxidants

Stable. Incompatible with strong oxidizing agents.

P201, P202, P273, P281, P308+P313, P391, P405, P501

H350

Strong reducers.

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.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H350: May cause cancer [Danger Carcinogenicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|H350 (100%): May cause cancer [Danger Carcinogenicity]|Aggregated GHS information provided by 42 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P281, P308+P313, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)|Use water spray.

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)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possbility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|For more Personal Protective Equipment (PPE) (Complete) data for P-NITROBIPHENYL (6 total), please visit the HSDB record page.|(See protection codes)

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.

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.

Eye irritant.

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.

NIOSH recommends that 4-nitrobiphenyl be regulated as a potential human carcinogen.|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.

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.

Separated from strong reducing agents. Well closed.

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

The substance is irritating to the eyes.

This substance is probably carcinogenic to humans.

NO open flames.

PREVENT DISPERSION OF DUST! STRICT HYGIENE! AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

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

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.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

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.

p-Nitrobiphenyl was analyzed for, but not detected (detection limit 0.68-3.2 ug/g), in particulate material collected from the exhaust of a heavy-duty diesel engine(1).

moderately toxic

LD50 Rabbit oral 1.97 g/kg|LD50 Rat oral 2.23 g/kg

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)

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 rate constant for the gas-phase reaction between p-nitrobiphenyl and hydroxyl radicals can be estimated to be 2.36X10-12 cu cm/molecule-sec at 25 °C which corresponds to a half-life of about 6.8 days in an average atmosphere containing 5X10+5 OH radicals/cu cm(1,SRC). p-Nitrobiphenyl has a uv absorption max at 295 nm(2) which suggests a potential for direct photolysis in the environment(SRC). Exposure of p-nitrobiphenyl (6.7 g/L) in a diethylamine solvent to uv irradiation above 290 nm for 3 hr resulted in 99% degradation(3); the degradation products were primarily azo aromatics(3). Aromatic nitro compounds are generally resistant to hydrolysis in water at pH 5-9(4); therefore, p-nitrobiphenyl is not expected to hydrolyze in the environment(SRC).

Based upon an estimated log Kow of 3.77(1), the BCF for p-nitrobiphenyl can be estimated to be 432 from a recommended regression equation(2,SRC). This estimated BCF value suggests that moderate bioconcentration may occur(SRC).

Based upon an estimated log Kow of 3.77(1), the Koc for p-nitrobiphenyl can be estimated to range from 2680 to 3360 using various regression-derived equations(2,SRC). These Koc estimates indicate very low soil mobility(3).

The Henry's Law Constant for p-nitrobiphenyl can be estimated to be 3.54X10-6 atm-cu m/mole at 25 °C using a structure estimation method(1,SRC). This value of Henry's Law Constant indicates slow volatilization from environmental waters, although volatilization from shallow rivers may have some significance(2). The volatilization half-life from a model river (1 meter deep flowing 1 m/sec with a wind speed of 3 m/sec) has been estimated to be 14.8 days(2,SRC); however, this estimation neglects the potentially significant effect of adsorption(SRC). The volatilization half-life from an environmental pond, which considers the effect of adsorption, can be estimated to be 1453 days(3,SRC); if parameters are introduced into the pond model to exclude the adsorption effects of p-nitrobiphenyl's log Kow of 3.77, the volatilization half-life is reduced to 160 days(SRC).

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. p-Nitrobiphenyl was formerly used in the manufacture of 4-diphenylamine(1). No data are available to suggest that p-nitrobiphenyl is inadvertently formed during any commercial process or in the environment. Therefore, exposure to the general population is not likely to occur. Exposure may be possible through contact with hazardous waste which was disposed of in past years. Laboratory workers handling reagent grades of p-nitrobiphenyl may be subject to exposure through dermal contact or inhalation(SRC).

4-NITRODIPHENYL ... KNOWN TO READILY PENETRATE INTACT SKIN.

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.

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.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Headache, drowsiness, dizziness; dyspnea (breathing difficulty); ataxia, lassitude (weakness, exhaustion); methemoglobinemia; urinary burning; acute hemorrhagic cystitis; [potential occupational carcinogen] Target Organs: Bladder, blood (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)

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.

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.

4-nitrobiphenyl

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

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

See Effects of long-term or repeated exposure.

MAY BE ABSORBED!

Redness.

Bladder, blood

100% USED FORMERLY AS AN INT FOR 4-AMINOBIPHENYL (1970)

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.

AROMATIC NITRO CMPD MAY BE QUANTITATIVELY CONVERTED TO AROMATIC AMINES & ... DETERMINED USING GUIDELINES SUGGESTED FOR LATTER CLASS OF CMPD ... .|... EST OF 4-NITROBIPHENYL USING ABSORPTION SPECTROMETRY HAVE BEEN DEVELOPED. ...|GAS CHROMATOGRAPHY /ELECTRON CAPTURE NEGATIVE ION CHEMICAL IONIZATION MASS SPECTROMETRY WAS SHOWN TO BE A VERY SENSITIVE AND SELECTIVE DETERMINATION METHOD FOR NITRATED POLYCYCLIC AROMATIC HYDROCARBONS. THE DETECTION LIMIT WAS 1 PG INJECTED TO THE GAS CHROMATOGRAPH COLUMN USING SINGLE ION MONITORING. THE METHOD WAS DEMONSTRATED ON A SYNTHETIC MIXT CONTAINING NITRO-POLYCYCLIC AROMATIC HYDROCARBONS. AND ON A TOLUENE EXTRACT OF A FORMERLY COMMERCIAL CARBON BLACK.|NIOSH Method 273. Analyte: 4-nitrobiphenyl. Matrix: Air. Procedure: Analysis by gas chromatography. Method Evaluation: Method was validated over the range of 4 to 2200 ug/cu m using a 50-liter sample. Method detection limit: 0.05 ug/sample. Interferences: None identified.|For more Analytic Laboratory Methods (Complete) data for P-NITROBIPHENYL (6 total), please visit the HSDB record page.

Hazardous Air Pollutants (HAPs)