description Chemical Properties Reactions Uses Production Method Toxicity Limited use
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Biphenyl

description Chemical Properties Reactions Uses Production Method Toxicity Limited use
Product Name
Biphenyl
CAS No.
92-52-4
Chemical Name
Biphenyl
Synonyms
PHPH;cp390;Xenene;mcs1572;Lemonene;DIPHENYL;BIPHENYL;Bibenzene;carolidal;FEMA 3129
CBNumber
CB2491271
Molecular Formula
C12H10
Formula Weight
154.21
MOL File
92-52-4.mol
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Biphenyl Property

Melting point:
68-70 °C (lit.)
Boiling point:
255 °C (lit.)
Density 
0.992
vapor density 
5.31 (vs air)
vapor pressure 
9.46 mm Hg ( 115 °C)
FEMA 
3129 | BIPHENYL
refractive index 
1.475
Flash point:
113 °C
storage temp. 
Store below +30°C.
solubility 
Soluble in alcohol and ether
form 
Crystalline Powder, Crystals or Flakes
Specific Gravity
0.992
color 
White to faint yellow
Odor
pleasant odor
explosive limit
0.6%, 111°F
Water Solubility 
insoluble
Merck 
14,3314
JECFA Number
1332
BRN 
1634058
Henry's Law Constant
2.92 at 25 °C (air stripping-GC, Destaillats and Charles, 2002)
Exposure limits
NIOSH REL: TWA 0.2 ppm, IDLH 100 mg/m3; OSHA PEL: TWA 0.2 ppm; ACGIH TLV: TWA 0.2 ppm.
Stability:
Stable. Combustible. Incompatible with strong oxidising agents.
InChIKey
ZUOUZKKEUPVFJK-UHFFFAOYSA-N
CAS DataBase Reference
92-52-4(CAS DataBase Reference)
NIST Chemistry Reference
Biphenyl(92-52-4)
EPA Substance Registry System
Biphenyl (92-52-4)
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Safety

Hazard Codes 
Xi,N,Xn,F,T
Risk Statements 
36/37/38-50/53-67-65-62-48/20-11-39/23/24/25-23/24/25-52/53
Safety Statements 
23-60-61-62-36/37-33-29-16-9-45
RIDADR 
UN 3077 9/PG 3
WGK Germany 
2
RTECS 
DU8050000
Autoignition Temperature
570 °C
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29029030
Hazardous Substances Data
92-52-4(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 3280 mg/kg (Deichmann)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H370Causes damage to organs

H372Causes damage to organs through prolonged or repeated exposure

H373May cause damage to organs through prolonged or repeated exposure

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P311Call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

P391Collect spillage. Hazardous to the aquatic environment

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
35800
Product name
Biphenyl
Purity
PESTANAL , analytical standard
Packaging
1g
Price
$17.6
Updated
2021/03/22
Sigma-Aldrich
Product number
8.03090
Product name
Biphenyl
Purity
for synthesis
Packaging
100 g
Price
$21.09
Updated
2021/03/22
Sigma-Aldrich
Product number
48161
Product name
Biphenyl solution
Purity
certified reference material, 2000?μg/mL in methanol
Packaging
1 mL
Price
$33.2
Updated
2021/03/22
Sigma-Aldrich
Product number
8.03090
Product name
Biphenyl
Purity
for synthesis
Packaging
1 kg
Price
$50.87
Updated
2021/03/22
Sigma-Aldrich
Product number
PHR2358
Product name
Biphenyl
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1G
Price
$149
Updated
2021/03/22
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Biphenyl Chemical Properties,Usage,Production

description

Biphenyl is also called phenyl benzene, it is formed by two connected phenyl compounds, is white or colorless to light yellow crystal plate, industrial products is slightly yellow with special fragrance. The melting temperature is 69.2 ℃, boiling point is 69.2 ℃. Insoluble in water, but soluble in organic solvents. Commonly used for organic synthesis precursor, is one of the key components of the organic high temperature heating medium. Its derivatives include benzidine, diphenyl ether, eight bromine diphenyl ether, polychlorinated biphenyls, etc.

Natural biphenyl exists in coal tar, crude oil and natural gas, the mass fraction is 0.20% to 0.20% in coal tar, current preparation methods of biphenyl include coal tar extraction and chemical synthesis.
The chemical bond in the middle of biphenyls can rotate freely, but if there were bulky groups in the four orthos, restricts rotation and would produce resistance isomer. This type of compounds (such as BINAP) can be used as a chiral ligands. substituted biphenyl by Suzuki reaction and Ullmann coupling reactions.
Biphenyl is a kind of important organic raw materials, widely used in medicine, pesticides, dyes, liquid crystal materials, etc. Can be used in the synthesis of plasticizer, preservatives, can also be used to make fuel, engineering plastic and high energy fuel.

Chemical Properties

Biphenyl is a white or slightly yellow scaly crystal, has a unique fragrance. Insoluble in water, acid and alkali, soluble in alcohol, ether, benzene and other organic solvents.

Reactions

Biphenyl is a neutral molecule and fairly non-reactive due to lack of functional group. However, biphenyl participates in many of the reactions that are typical for benzene, for example, substitution reactions upon treatment with halogens in the presence of a Lewis acid. Also, it is required to convert biphenyls into the structural analogs containing the active groups in order for it to be able to use for synthetic intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, plastics and pharmaceuticals (Johansson and Olsen, 2008). For this, it is important to consider the o,p-directing and/or mdirecting effect, especially when substitution at a specific position is desired i.e. mono, di-, tri- or tetra- substitutions. It is possible to acetylate the carboxylic part, also various other biphenyl derivative synthesis are possible by carrying out the amination, halogenation, sulphonation, alkylation, hydroxylation, metal complexation etc.

Uses

Biphenyl is used in organic syntheses, heat transfer fluids, dye carriers, food preservatives, as an intermediate for polychlorinated biphenyls, and as a fungistat in the packaging of citrus fruits.
Biphenyl with high thermal stability and low vapor pressure, long often alone or with diphenyl ether and blend to used as heating medium. Component of biphenyl and terphenyl (including Biphenyl 13%, terphenyl 61%) can effectively absorb radiation, can be used as a heating medium for nuclear power plant. And three terphenyl([91-94-4]) is the byproduct of benzene pyrolysis to produce Biphenyl, according to the different reaction conditions, the proportion of the reaction product of biphenyl and terphenyl within a certain range of change, in general, Biphenyl: terphenyl=78:1. Biphenyl is used as a carrier, and its derivatives of ethyl biphenyl, diethyl biphenyl and triethyl biphenyl senior can be used as solvents, used in pressure sensitive dye solvent of carbon paper.

Production Method

Biphenyl occurs naturally in coal tar, crude oil, and natural gas and can be isolated from these sources via distillation. It can also be synthesized synthetically by using a Grignard reagent such as phenylmagnesium bromide and reacting it with bromobenzene, reacting fluorobenzene with phenyl lithium or reacting benzyne with phenyl lithium as follows.
Ullmann et al. (1904), discovered that heating iodobenzene with a copper powder catalyst leads to the formation of biphenyl with high purity. Meanwhile, this reaction has become a textbook case and it is widely used in synthetic chemistry due to its versatility in the association of substituted phenyls to complex biphenyl derivatives.
The synthesis of biphenyl out of iodobenzene on copper essentially consists of three steps: dissociation of iodobenzene (C6H5I) to phenyl (C6H5) and iodine, diffusion of phenyl to find another phenyl as a reaction partner, and association to form biphenyl (C12H10). The dissociation of iodobenzene by thermal activation takes place at 180 K and biphenyl is formed at 210 K for multilayer (Weiss et al., 1998) and 300 K for submonolayer iodobenzene on Cu(III) [Yang et al., 1995; Xi and Bent, 1992].

Toxicity

ADI 0~0.05 mg/kg (under some conditions 0.05~0.25 mg/kg FAO/WHO, 2001).
LD50 3.28~5.04 g/kg (mice, through the mouth).

Limited use

FAO/WHO, the United States and Canada regulations, its residual ≤110 mg/kg or less; Japan, France, Germany, the Netherlands, rules ≤70 mg/kg or less.

Description

Biphenyl, also called diphenyl, consists of two benzene rings joined by a single bond. It exists as colorless to yellowish crystals, has a distinctive odor, and occurs naturally in oil, natural gas, and coal tar.

Chemical Properties

1,1'-Biphenyl is a clear colorless liquid with a pleasant odor and stable organic compound. It is combustible at high temperatures, producing carbon dioxide and water when combustion is complete. Partial combustion produces carbon monoxide, smoke, soot, and low molecular weight hydrocarbons. It is used extensively in the production of heat-transfer fl uids, for example, as an intermediate for polychlorinated biphenyls, and dye carriers for textile dyeing. It is also used as a mold retardant in citrus fruit wrappers, in the formation of plastics, optical brighteners, and hydraulic fluids.

Physical properties

White scales with a pleasant but peculiar odor. Odor threshold concentration is 0.83 ppb (quoted, Amoore and Hautala, 1983).

Occurrence

Reported found in coal tar, bilberry, carrots, peas, potato, bell pepper, rum, cocoa, tomato, coffee, roasted peanuts, olive (Olea europae), buckwheat and tamarind (Tamarindus indica L).

Uses

Biphenyl is used as an antifungal agent to preserve citrus fruit, in citrus wrappers to retard mold growth, in heat transfer fluids, in dye carriers for textiles and copying paper, as a solvent in pharmaceutical production, in optical brighteners, and as an intermediate for the production of a wide range of organic compounds.

Uses

Biphenyl is used to prevent fungal attack on stored citrus fruit. It is impregnated into fruit wraps.

Uses

As heat transfer agent; fungistat for oranges (applied to inside of shipping container or wrappers); in organic syntheses.

Definition

ChEBI: A benzenoid aromatic compound that consists of two benzene rings connected by a single covalent bond. Biphenyl occurs naturally in coal tar, crude oil, and natural gas. Formerly used as a fungicide for citrus crops.

Definition

An organic compound having a structure in which two phenyl groups are joined by a C–C bond.

Preparation

By thermal dehydrogenation of benzene.

Aroma threshold values

Detection: 0.5 ppb

Synthesis Reference(s)

Journal of the American Chemical Society, 83, p. 1251, 1961 DOI: 10.1021/ja01466a056
Tetrahedron Letters, 25, p. 391, 1984 DOI: 10.1016/S0040-4039(00)99891-5

General Description

A clear colorless liquid with a pleasant odor. Flash point 180°F. Insoluble in water. Vapors are heavier than air. Used to manufacture other chemicals and as a fungicide.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Biphenyl is incompatible with oxidizers.

Health Hazard

Exposures to 1,1’-biphenyl cause acute effects with symptoms that include, but are not limited to, polyuria, accelerated breathing, lacrimation, anorexia, weight loss, muscular weakness, coma, fatty liver cell degeneration, and severe nephrotic lesions. Exposure to biphenyl fumes for short periods of time causes nausea, vomiting, irritation of the eyes and respiratory tract, and bronchitis. Breathing small amounts of 1,1’-biphenyl over long periods of time causes damage to the liver and the nervous system of exposed workers. Breathing the mists, vapors, or fumes may irritate the nose, throat, and lungs. Depending on the concentration and duration of exposure, the symptoms include, but are not limited to, sore throat, coughing, labored breathing, sneezing, a burning sensation, and the effects of CNS depression. Symptoms may include headache, excitation, euphoria, dizziness, incoordination, drowsiness, light-headedness, blurred vision, fatigue, tremors, convulsions, loss of consciousness, coma, respiratory arrest, and death, depending on the concentration and duration of exposure

Fire Hazard

Combustible. Emits toxic fumes under fire conditions.

Safety Profile

Poison by intravenous route.Moderately toxic by ingestion. A powerful irritant byinhalation in humans. Human systemic effects byinhalation of very small amounts: flaccid paralysis, nauseaor vomiting, and other unspecified gastrointestinal effects.Que

Potential Exposure

Biphenyl is a fungicide (pesticide). It is also used as a heat transfer agent, dye carrier, and as an intermediate in organic synthesis.

Source

Present in coal tar at a concentration of 2.72 mg/g (Lao et al., 1975). Detected in woodpreserving creosotes at a concentration of 2.1 wt % (Nestler, 1974). Typical concentration of biphenyl in a heavy pyrolysis oil is 2.3 wt % (Chevron Phillips, May 2003).

Environmental Fate

Biological. Reported biodegradation products include 2,3-dihydro-2,3-dihydroxybi phenyl, 2,3-dihydroxybiphenyl, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate, 2-hydroxy- 3-phenyl-6-oxohexa-2,4-dienoate, 2-oxopenta-4-enoate, phenylpyruvic acid (Verschueren, 1983), 2-hydroxybiphenyl, 4-hydroxybiphenyl and 4,4′-hydroxybiphenyl (Smith and Rosazza, 1974). Under aerobic conditions, Beijerinckia sp. degraded biphenyl to cis-2,3- dihydro-2,3-dihydroxybiphenyl. In addition, Oscillatoria sp. and Pseudomonas putida degraded biphenyl to 4-hydroxybiphenyl and benzoic acid, respectively (Kobayashi and Rittman, 1982). The microbe Candida lipolytica degraded biphenyl into the following products: 2-, 3- and 4-hydroxybiphenyl, 4,4′-dihydroxybiphenyl and 3-methoxy-4-hydrox ybiphenyl (Cerniglia and Crow, 1981). With the exception of 3-methoxy-4-hydroxybiphe nyl, these products were also identified as metabolites by Cunninghanella elegans (Dodge et al., 1979). In activated sludge, 15.2% mineralized to carbon dioxide after 5 days (Freitag et al., 1985).
Photolytic. A carbon dioxide yield of 9.5% was achieved when biphenyl adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 hours. Irradiation of biphenyl (λ >300 nm) in the presence of nitrogen monoxide resulted in the formation of
Chemical/Physical. The aqueous chlorination of biphenyl at 40°C over a pH range of 6.2 to 9.0 yielded o-chlorobiphenyl and m-chlorobiphenyl (Snider and Alley, 1979). In an acidic aqueous solution (pH 4.5) containing bromide ions and a chlorinatin
Biphenyl will not hydrolyze since it has no hydrolyzable functional group.

Metabolic pathway

Biphenyl is a stable compound. It has a restricted use as a fungistat applied to citrus packing material. This has generated studies on its toxicity and metabolism in mammals and residue studies in stored fruit. Only limited information on its environmental fate has been published.

storage

1,1’-Biphenyl should be kept stored in tightly closed containers in a cool, dry, isolated, and properly ventilated area, away from heat, sources of ignition, incompatibles, and contact with strong oxidizers.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.

Purification Methods

Crystallise biphenyl from EtOH, MeOH, aqueous MeOH, pet ether (b 40-60o) or glacial acetic acid. Free it from polar impurities by passage through an alumina column in *benzene, followed by evaporation. The residue has been purified by distillation in a vacuum and by zone refining. Treatment with maleic anhydride removes anthracene-like impurities. It has been recrystallised from EtOH followed by repeated vacuum sublimation and passage through a zone refiner. [Taliani & Bree J Phys Chem 88 2351 1984, Beilstein 5 H 576, 5 I 271, 5 II 479, 5 III 1726, 5 IV 1807.]

Degradation

Biphenyl is not subject to hydrolysis.

Incompatibilities

Mist may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Precautions

Occupational workers should be careful during use and chemical management because the fi nely dispersed particles of 1,1’-biphenyl form explosive mixtures in air

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Biphenyl Suppliers

Kingfirst Chemical (Nanjing) Co.,Ltd
Tel
+86-025-84522992 84524602 13805186390
Fax
+86 025 84521617
Email
marketing@kingfirstchem.com
Country
China
ProdList
74
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58
Shanghai Yanze Chemical Co., Ltd.
Email
379052146@qq.com
Country
CHINA
ProdList
69
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58
Jobachem Suzhou Co., Ltd
Tel
0512-62927368
Email
xiaomin.cheng@jobachem.com;jing.ding@jobachem.com
Country
China
ProdList
44
Advantage
58
Shanghai Jiaoze Industrial Co., LTD
Tel
021-37318802-
Fax
021-37318802
Email
liangpanpan@sh-jiaoze.com
Country
China
ProdList
202
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58
Shanghai zhiping biology science and technology co., ltd
Tel
Email
494972302@qq.com
Country
China
ProdList
18
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58
Creasyn Finechem(Tianjin) Co., Ltd.
Tel
022-83945878-
Fax
022-83945176
Email
export@creasyn.com
Country
China
ProdList
731
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68
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
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76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30159
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View Lastest Price from Biphenyl manufacturers

Shijiazhuang tongyang Import and Export Co., LTD
Product
Biphenyl 92-52-4
Price
US $26.00/KG
Min. Order
1g
Purity
99.9%
Supply Ability
500000kgs
Release date
2021-08-13
Hebei Guanlang Biotechnology Co., Ltd.
Product
Nisin 92-52-4
Price
US $1.00/PCS
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-08-09
Baoji Guokang Bio-Technology Co., Ltd.
Product
Biphenyl 92-52-4
Price
US $2910.00/T
Min. Order
1T
Purity
98%
Supply Ability
1-200mt
Release date
2021-06-09

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