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92-52-4

Basic Information
CAS No.: 92-52-4
Name: Biphenyl
Article Data: 3215
Cas Database
Molecular Structure:
Molecular Structure of 92-52-4 (Biphenyl)
Formula: C12H10
Molecular Weight: 154.211
Synonyms: 1,1'-Biphenyl;Dipheny;Biphenyl(8CI);1,1'-Diphenyl;Bibenzene;Carolid AL;Diphenyl;NSC 14916;Phenylbenzene;Tetrosin LY;
EINECS: 202-163-5
Density: 0.997 g/cm3
Melting Point: 68-70 °C(lit.)
Boiling Point: 257.956 °C at 760 mmHg
Flash Point: 105.492 °C
Solubility: insoluble in water
Appearance: white crystals
Hazard Symbols: HarmfulXn, IrritantXi, DangerousN, FlammableF, ToxicT
Risk Codes: 36/37/38-50/53-67-65-62-48/20-11-39/23/24/25-23/24/25
Safety: 23-60-61-62-36/37-33-29-16-9-45
Transport Information: UN 3077 9/PG 3
PSA: 0.00000
LogP: 3.35360
Synthetic route
132-65-0

dibenzothiophene

92-52-4

biphenyl

Conditions
ConditionsYield
With Ni-MoS2 supported on γ-Al2O3 at 320℃; Temperature; Reagent/catalyst;100%
With 3-Hydroxy-1-methylpiperidine; nickel diacetate; sodium hydride In tetrahydrofuran at 65℃; for 1.25h;95%
With lithium aluminium tetrahydride; (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel In tetrahydrofuran at 55 - 60℃; for 48h; Product distribution; further reagent ratio;90%
108-86-1

bromobenzene

92-52-4

biphenyl

Conditions
ConditionsYield
With palladium diacetate; triethylamine; 2-diphenylphosphino-2'-methylbiphenyl In N,N-dimethyl-formamide at 100℃; for 5h; Ullmann reaction; Inert atmosphere;100%
With potassium carbonate In ethanol; water at 20℃; for 12h; Ullmann Condensation;100%
dibromobis(triphenylphosphine)nickel(II); tetraethylammonium iodide; zinc In tetrahydrofuran at 50℃; for 1.5h;99%
591-50-4

iodobenzene

92-52-4

biphenyl

Conditions
ConditionsYield
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 2h; Microwave irradiation;100%
With sodium tetraphenyl borate; sodium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 4h; Suzuki coupling; Inert atmosphere;99%
With potassium carbonate In ethanol; water at 80℃; for 4h; Reagent/catalyst; Solvent; Ullmann Condensation; Green chemistry;99.2%
2051-61-8

m-chlorobiphenyl

92-52-4

biphenyl

Conditions
ConditionsYield
With water In ethanol for 30h; Irradiation; Sealed tube; Inert atmosphere;100%
With water; potassium formate at 100℃; for 24h; Inert atmosphere;91%
With sodium hydroxide; Raney Ni-Al alloy In water at 60℃; for 2h; Irradiation;83%
92-66-0

4-bromo-1,1'-biphenyl

92-52-4

biphenyl

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; for 24h;100%
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran at -50℃; for 0.5h;
Stage #2: With phenylacetonitrile In tetrahydrofuran at -50 - 20℃; for 0.5h; Further stages;
99%
With [RhCl2(p-cymene)]2; potassium tert-butylate In isopropyl alcohol at 20 - 100℃; for 24h; Inert atmosphere;97%
100-58-3

phenylmagnesium bromide

92-52-4

biphenyl

Conditions
ConditionsYield
With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone at -20℃; Product distribution / selectivity;100%
With iron(III) chloride; 1,2-dichloro-ethane In tetrahydrofuran at 0℃; for 0.0833333h; Ionic liquid; Inert atmosphere;100%
With 1,2-bisperfluorotolyl-3,3,4,4,5,5-hexafluorocyclopentene In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere;99%
603-33-8

triphenylbismuthane

92-52-4

biphenyl

Conditions
ConditionsYield
With triethylamine; palladium diacetate In N,N,N,N,N,N-hexamethylphosphoric triamide at 65℃; for 0.166667h;100%
With para-bromotoluene; C22H25ClNPPdS; potassium carbonate In 1,4-dioxane at 100℃; for 6h; Inert atmosphere; Schlenk technique;48%
With 2-thioxo-3H-1,3-benzothiazole; copper diacetate; bis(dibenzylideneacetone)-palladium(0) In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;19 %Chromat.
507233-69-4, 594-30-9, 28719-54-2

triphenyl bismuth (2+); dichloride

92-52-4

biphenyl

Conditions
ConditionsYield
With triethylamine; palladium diacetate In tetrahydrofuran for 0.5h; Ambient temperature;100%
108-90-7

chlorobenzene

100-58-3

phenylmagnesium bromide

92-52-4

biphenyl

Conditions
ConditionsYield
nickel(II) In tetrahydrofuran for 18h; Product distribution; other catalyst, other solvents; other Grignard compounds and alkyl or vinyl halides;100%
With CpNi[1-(ethoxycarbonyl)methyl-3-(3,5-dimethylbenzyl)benzimidazolin-2-ylidene]Br In tetrahydrofuran at 25℃; for 3h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;97%
With Pd/Al(OH)3 In toluene at 140℃; for 36h; Kumada Cross-Coupling; Inert atmosphere;94%
108-90-7

chlorobenzene

98-80-6

phenylboronic acid

92-52-4

biphenyl

Conditions
ConditionsYield
With Cs2O3; PCy3 adduct of cyclopalladated ferrocenylimine In 1,4-dioxane at 100℃; for 15h; Suzuki cross-coupling reaction;100%
With dichloro(cycloocta-1,5-diene)palladium (II); 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); potassium carbonate In methanol for 0.166667h; Suzuki cross-coupling reaction; Microwave irradiation; Inert atmosphere;100%
With potassium carbonate In methanol at 100℃; for 0.0833333h; Suzuki-Miyaura Coupling; Microwave irradiation;100%
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    Product Name: Biphenyl Synonyms: PHENYL BENZENE;1,1'-biphenyl;1,1'-Diphenyl;DIPHENYL;'LGC' (1606);'LGC' (2610);FEMA 3129;BIPHENYL CAS: 92-52-4 MF: C12H10 MW: 154.21 EINECS: 202-163-5398- App

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    92-52-4

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Consensus Reports

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

Standards and Recommendations

OSHA PEL: TWA 0.2 ppm
ACGIH TLV: TWA 0.2 ppm
DFG MAK: 0.16 ppm (1 mg/m3)

Analytical Methods

For occupational chemical analysis use NIOSH: Biphenyl, 2530.

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.