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Biphenyl(CAS No. 92-52-4)

Biphenyl C12H10 (cas 92-52-4) Molecular Structure

92-52-4 Structure

Identification and Related Records

【Name】
Biphenyl
【CAS Registry number】
92-52-4
【Synonyms】
Diphenyl Mixture
Diphenyl
【EINECS(EC#)】
202-163-5
【Molecular Formula】
C12H10 (Products with the same molecular formula)
【Molecular Weight】
154.21
【Inchi】
InChI=1/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
【InChIKey】
ZUOUZKKEUPVFJK-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC=C(C=C1)C2=CC=CC=C2
【MOL File】
92-52-4.mol

Chemical and Physical Properties

【Appearance】
White crystals
【Density】
0.992
【Melting Point】
68.5-71℃
【Boiling Point】
255℃
【Refractive Index】
1.475
【Flash Point】
113℃
【Water】
insoluble
【Solubilities】
Insoluble
【Color/Form】
White scales
Colorless leaflets
Pure biphenyl is a white crystalline solid that separates from solvents as plates or monoclinic prismatic crystals. Commercial samples are often slightly yellow or tan in color.
【Stability】
Stable. Combustible. Incompatible with strong oxidising agents.
【HS Code】
29029030
【Storage temp】
0-6°C
【Spectral properties】
Index of refraction: 1.475 @ 20 deg C/D; 1.588 @ 75 deg C/D
MAX ABSORPTION (ALCOHOL): 247 NM (LOG E= 4.24); SADTLER REF NUMBER: 783 (IR, PRISM); 163 (IR, GRATING)
Intense mass spectral peaks: 154 m/z (100%), 153 m/z (31%), 152 m/z (28%), 76 m/z (17%)
IR: 6024 (Coblentz Society Spectral Collection)
UV: 255 (Sadtler Research Laboratories Spectral Collection)
13C NMR: 90 (Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York)
NMR: 289 (Varian Associates NMR Spectra Catalogue)
MASS: 60914 (NIST/EPA/MSDC Mass Spectral Data base, 1990 version)
【Computed Properties】
Molecular Weight:154.2078 [g/mol]
Molecular Formula:C12H10
XLogP3:4
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:1
Exact Mass:154.07825
MonoIsotopic Mass:154.07825
Topological Polar Surface Area:0
Heavy Atom Count:12
Formal Charge:0
Complexity:100
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Ring Count:2
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38;R50/53
【Safety Statements 】
S23;S60;S61
【HazardClass】
9
【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
In acute exposure, diphenyl causes eye and skin irritation... .
Causes irritation to eyes, skin, and mucous membrane and upper respiratory tract.
【Cleanup Methods】
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.
Remove all ignition sources. Ventilate area of spill. For small quant, sweep onto paper or other suitable material, place in an appropriate container and burn in a safe place (such as a fume hood). Large quant may be reclaimed; however, if this is not practical, use a procedure similar to that for small quant.
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.
AEROBIC: Numerous screening studies with activated sludge as microbial inoculum, conducted to assess the biodegradation potential of biphenyl, have shown that the compound is biodegradable(1-5). Biphenyl, at 100 mg/l, reached 66% of the theoretical BOD after 2 weeks using an activated sludge inoculum(6). Acclimation of the microbial population may increase the biodegradation rate of biphenyl(5).
ANAEROBIC: The biodegradation of biphenyl was very slow under anaerobic conditions(1). Biphenyl at 50 mg COD/l under aerobic conditions was readily biodegraded; under anoxic/nitrate or anaerobic/methane generating conditions biphenyl was not biodegraded(2). Biphenyl was degraded using anaerobic batch reactors, rate not specified(3).
【Transport】
UN 3077
【Fire Fighting Procedures】
Carbon dioxide, dry chemical, water spray, mist, fog.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.
【Fire Potential】
Slight when exposed to heat or flame; can react with oxidizing materials.
【Formulations/Preparations】
PHPH
XENENE
LEMONENE
PHENADOR-X
Carolid AL
Bulk molten or flaked, technical grades (99.9% purity). /Monsanto Co/
95% and 99% molten or flake grades. /Sybron Chemicals, Inc/
Technical grade of 93-97% purity. High purity is greater than or equal to 99.9% purity.
【Reactivities and Incompatibilities】
Reacts with oxidants causing fire and explosion hazard.
Dust explosion possible if in powder form, mixed with air.
【Other Preventative Measures】
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
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.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
Avoid prolonged skin contact. Keep away from eyes. Do not inhale spray mist.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Wash away any material which may have contacted the body with copious amounts of water or soap and water.
The basic ventilation methods are local exhaust ventilation and dilution or general ventilation.
【Protective Equipment and Clothing】
Appropriate garments, gloves, and respiratory equipment should be available.
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 possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. /Molten/
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.] /Molten/
Respirator Recommendations: Up to 10 mg/cu m: (Assigned protection factor= 10) Any chemical cartridge respirator with organic vapor cartridge(s) in combination with a dust and mist filter/ (Assigned protection factor = 10) Any supplied-air respirator.
Respirator Recommendations: Up to 25 mg/cu m: (Assigned protection factor = 25) Any supplied-air respirator operated in a continuous flow mode. (Substance reported to cause eye irritation or damage; may require eye protection)/ (Assigned protection factor = 25) Any powered, air-purifying respirator with organic vapor cartridge(s) in combination with a dust and mist filter. (Substance reported to cause eye irritation or damage; may require eye protection).
Respirator Recommendations: Up to 50 mg/cu m: (Assigned protection factor = 50) Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter/(Assigned protection factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter/(Assigned protection factor = 50) Any powered, air-purifying respirator with a tight-fitting facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. (Substance reported to cause eye irritation or damage; may require eye protection)./(Assigned protection factor = 50) Any self-contained breathing apparatus with a full facepiece/(Assigned protection factor = 50) Any supplied-air respirator with a full facepiece.
Respirator Recommendations: Up to 100 mg/cu m: (Assigned protection factor = 2000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode.
Respirator Recommendations: Emergency or planned entry into unknown concn or IDLH conditions: (Assigned protection factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode/(Assigned protection factor = 10,000 0) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape: (Assigned protection factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter/ Any appropriate escape-type, self-contained breathing apparatus.
【Specification】

The Biphenyl ,?with cas registry number of 92-52-4,?has other registry numbers including?56481-93-7,?72931-46-5. It belongs to?classification codes which are?(1)Agricultural Chemical ; (2)Fungicide, bactericide, wood preservative ; (3)Fungicides, industrial ; (4)Human Data ; (5)Mutation data ; (6)Pesticides ; (7)Skin / Eye Irritant ; (8)TSCA Flag T [Subject to the Section 4 test rule under TSCA] ; (9)Tumor data ; (10)Unspecified / Unclassified pesticide. Its systematic name is called biphenyl?. And its IUPAC name is known as 1,1'-biphenyl . This chemical is stable but?incompatible with strong oxidising agents. Store it at temperature of 0-6°C.

Physical properties about this chemical are:?(1) ACD/LogP: 3.98 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): 3.98 ; (4) ACD/LogD (pH 7.4): 3.98 ; (5) ACD/BCF (pH 5.5): 618.76 ; (6) ACD/BCF (pH 7.4): 618.76 ; (7) ACD/KOC (pH 5.5): 3465.55 ; (8) ACD/KOC (pH 7.4): 3465.55 ; (9) #H bond acceptors: 0 ; (10) #H bond donors: 0 ; (11) #Freely Rotating Bonds: 1 ; (12) Index of Refraction: 1.571; (13) Molar Refractivity: 50.84 cm3 ; (14) Molar Volume: 154.7 cm3 ; (15) Surface Tension: 36.6 dyne/cm; (16) Density: 0.996 g/cm3 ; (17) Flash Point: 105.5 °C ; (18) Enthalpy of Vaporization: 47.55 kJ/mol ; (19) Boiling Point: 258 °C at 760 mmHg ; (20) Vapour Pressure: 0.0227 mmHg at 25°C ; (21) Refractive index: 1.475.

Preparation of?Biphenyl : this chemical can be prepared by?dibenzothiophene .


This reaction will need reagents N-methyl-3-hydroxypiperidine, NaH, Ni (OAc)2, solvent tetrahydrofuran at temperature 65 ℃. The reaction time is 1.25 hours. The yield is about 95%.

Uses of?Biphenyl : (1)it?is commonly used as the raw materials for engineering plastics polysulfone which is used to produce trichloro biphenyl, biphenyl pentachlorophenol,and can be used as heat carrier, preservatives, dyes, etc. (2) it can be used to produce other chemicals such as?bicyclohexyl .


This reaction?occurs at temperature 160 ℃ using reagents MmNi3.5Co0.7Al0.8H4 under reaction pressure 3677.5. The reaction time is 3 hours. The yield is about 95%.

When you are using this chemical, please be cautious about it as the following:
Poison by intravenous route. Moderately toxic by ingestion. A powerful irritant by inhalation in humans. Human systemic effects by inhalation of very small amounts: flaccid paralysis, nausea or vomiting, and other unspecified gastrointestinal effects. Questionable carcinogen with experimental tumorigenic and neoplastigenic data. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO2, dry chemical, water spray, mist, fog. When heated to decomposition it emits acrid smoke and fumes.

You can still convert the following datas into molecular structure:
(1)SMILES:c1cc(ccc1)c2ccccc2;
(2)InChI:InChI=1/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H;
(3)InChIKey:ZUOUZKKEUPVFJK-UHFFFAOYAV

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral > 2600mg/kg (2600mg/kg) ? "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A166, Pg. 1983,
human TCLo inhalation 4400ug/m3 (4.4mg/m3) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES
Archives of Environmental Health. Vol. 26, Pg. 70, 1973.
mouse LD50 intravenous 56mg/kg (56mg/kg) ? U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00198,
mouse LD50 oral 1900mg/kg (1900mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. Vol. 24, Pg. 268, 1983.
rabbit LD50 oral 2400mg/kg (2400mg/kg) ? Nagoya Shiritsu Daigaku Igakkai Zasshi. Journal of the Nagoya City University Medical Association. Vol. 28, Pg. 983, 1977.
rabbit LD50 skin > 5010mg/kg (5010mg/kg) ? Monsanto Co. Toxicity Information.
rat LC inhalation > 200mg/m3 (200mg/m3) ? Monsanto Co. Toxicity Information.
rat LD50 oral 2140mg/kg (2140mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION
National Technical Information Service. Vol. OTS0546109,
rat LD50 unreported 4500mg/kg (4500mg/kg) ? Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(5), Pg. 6, 1988.

【Octanol/Water Partition Coefficient】
log Kow = 4.01
【Report】

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory. Community Right-To-Know List.

【Disposal Methods】
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.
The following wastewater treatment technologies have been investigated for biphenyl: concentration process: Activated carbon.
The following wastewater treatment technologies have been investigated for biphenyl: Concentration process: Resin adsorption.
Incineration: Package in paper cartons or dissolve in a flammable solvent (waste alcohols) and burn in an approved incinerator.
By making package of diphenyl in paper or other flammable material and burning in a suitable combustion chamber. By dissolving diphenyl in a flammable solvent (such as alc) and atomizing in a suitable combustion chamber.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

... By heating bromobenzene and sodium, with subsequent distillation. /As well as/ by slowly passing benzene through a red-hot iron tube
/Produced/ by passing benzene vapors over ferroso-ferric or lead oxide at high temp, in small quantities.
... Suppliers recover biphenyl from high boiler fractions that accompany the hydrodealkylation of toluene to benzene. Numerous hydrodealkylation processes have been developed. Most have the common feature that toluene or other alkylbenzene plus hydrogen is passed under pressure through a tubular reactor at high temperature. Methane and benzene are the principal products formed. Dealkylation conditions are sufficiently severe to cause some dehydrocondensation of benzene and toluene molecules. Approximately 1 kg of biphenyl per 100 kg of benzene is produced.
High purity biphenyl is currently produced ... by direct dehydrocondensation of benzene.
Xylenol, mixed (fractionation/alkali extraction; co-produced with o-phenylphenol.
Diphenyl is made by the vapor-phase, noncatalytic pyrolysis of benzene in a tubular steel coil reactor at 600 to 800 deg C and atmospheric pressure for a contact time of 0.4 to 1.5 seconds. Yields are 85 to 90 percent.
Biphenyl is produced by reaction of phenylmagnesium bromide with 1,4-dimethyl-2,3-dibromobutane in an inert solvent.
U.S. Production

This chemical is listed as a High Production Volume (HPV) (65FR81686; http://www.epa.gov/opptintr/chemrtk/hpvchmlt.htm). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438; http://www.epa.gov/oppt/iur/index.htm).
(1988) No data provided
The 1990 figure is probably on the order of 16 million kg/yr.
【Usage】

Fungicide.

【Sampling Procedures】
NIOSH Method S24. Analyte: Biphenyl. Matrix: Air. Procedure: Adsorption on tenax gas chromatography. Flow Rate: 0.50 l/min or less. Sample Size: 30 liters.
NIOSH Method 2530. Analyte: Biphenyl. Matrix: Air. Sampler: Solid sorbent tube (Tenax GC, 20 mg/10 mg). Flow Rate: 0.01 to 0.5 l/min: Sample size; 30 liters. SHIPMENT: Routine. Sample Stability: 95% recovery after 7 days at room temperature.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
【Biomedical Effects and Toxicity】
Diphenyl is absorbed through the skin, the mucous membranes, and pulmonary system. It is metabolized in the liver to water-soluble hydroxy derivatives. Diphenyl is excreted unchanged by the biliary system of the rat when stimulated with phenobarbital intraperitoneally at 70 mg/kg for 4 days.
(14)C-Biphenyl was orally administered to rats and urine was collected. After 96 hours 92% of the radioactivity had been excreted. Urinary excretion accounted for more than 84% of the administered label (75.8% within 24 hours) and fecal excretion for 7.3% (5.8% within 24 hours) of the radioactivity.
The biliary excretion of metabolites of biphenyl ... was shown ... to be increased by pre-treatment with hepatic-microsomal-enzyme inducers and to be decreased by enzyme inhibitors after dosing with parent compounds, but no effect was observed after dosing with metabolites.
In rats, rabbits, and pigs, most biphenyl metabolites are excreted in the urine. Following an oral dose of 100 mg (14C)biphenyl/kg body weight, rats excreted 82% of the administered radioactivity (76% in urine) within 24 h. The recovery rate after 4 days was 92%, with 7% of the administered radioactivity detected in the feces and traces in the exhaled air. Eight days after administration, radioactivity in the tissues was 0.6% of the applied dose. In none of the species examined was unmetabolized biphenyl found in the urine.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 870-3,300(2), indicate that biphenyl is expected to have low to slight mobility in soil(SRC). Volatilization of biphenyl from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 3.08X10-4 atm-cu m/mole(3); however the importance of this process decreases with increasing soil depth(5). Biphenyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.93X10-3 mm Hg(4). However, adsorption to soil is expected to attenuate volatilization(SRC). As biphenyl absorbs very little light at wavelengths greater than 290 nm(5), direct photolysis should not be important(SRC). Test results indicate that biodegradation in soil is variable with 86% mineralized to carbon dioxide in 98 days using a Flanagan silt loam soil, and in an Altamont soil, 81% of biphenyl initially applied mineralized after 24 days(6). Acclimation plays a role in the rate as biodegradation amounted to 36% in 2 weeks in a diesel oil contaminated soil containing 31 mg/k biphenyl(7).
AQUATIC FATE: Based on a classification scheme(1), Koc values of 870 to 3,300(2), indicate that biphenyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 3.08X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hrs and 6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 41 days if adsorption is considered(5). According to a classification scheme(6), a BCF range of 280-4,500(7-10) suggests the potential for bioconcentration in aquatic organisms is high to very high(SRC). Biodegradation may be an important environmental fate process under aerobic conditions, as indicated by a reported half-life of 2-3 days in a river die-away test(11); however, the compound may be resistant to biodegradation under anaerobic conditions(12). Biodegradation of biphenyl may be very slow in unpolluted seawater(13).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), biphenyl, which has a vapor pressure of 8.93X10-3 mm Hg at 25 deg C(2), is expected to exist as a vapor in the ambient atmosphere. Vapor-phase biphenyl 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 2 days(SRC), calculated from its rate constant of 7.20X10-12 cu cm/molecule-sec at 25 deg C(3). Biphenyl has been found partly in the particle-sorbed phase in the atmosphere(4); therefore, particulate-phase biphenyl may be physically removed from the air by dry deposition(SRC). As biphenyl absorbs very little light at wavelengths above 290 nm(5) direct photolysis in air may not be an important process(SRC).

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