| Identification | More | [Name]
Biphenyl | [CAS]
92-52-4 | [Synonyms]
1,1'-biphenyl
1,1'-Diphenyl
BIPHENYL
DIPHENYL
FEMA 3129
'LGC' (1606)
'LGC' (2610)
PHENYL BENZENE
Bibenzene
Carolid al
carolidal
cp390
Lemonene
mcs1572
Phenador-X
PHPH
Tetrosin ly
tetrosinly
Xenene
Diphenyl Mixture | [EINECS(EC#)]
202-163-5 | [Molecular Formula]
C12H10 | [MDL Number]
MFCD00003054 | [Molecular Weight]
154.21 | [MOL File]
92-52-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Biphenyl is a combustible, white flakes or
crystalline solid. Pleasant, characteristic odor. | [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 | [refractive index ]
1.475 | [Fp ]
113 °C
| [storage temp. ]
0-6°C
| [solubility ]
Soluble in alcohol and ether | [form ]
Crystalline Powder, Crystals or Flakes | [color ]
White to faint yellow | [Specific Gravity]
0.992 | [Odor]
pleasant odor | [Stability:]
Stable. Combustible. Incompatible with strong oxidising agents. | [explosive limit]
0.6%, 111°F | [Odor Type]
green | [Water Solubility ]
insoluble | [JECFA Number]
1332 | [Merck ]
14,3314 | [BRN ]
1634058 | [Henry's Law Constant]
2.92 at 25 °C (air stripping-GC, Destaillats and Charles, 2002) | [Dielectric constant]
20.0（Ambient） | [Exposure limits]
NIOSH REL: TWA 0.2 ppm, IDLH 100 mg/m3; OSHA PEL: TWA
0.2 ppm; ACGIH TLV: TWA 0.2 ppm. | [InChIKey]
ZUOUZKKEUPVFJK-UHFFFAOYSA-N | [LogP]
4.008 at 25℃ | [CAS DataBase Reference]
92-52-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Biphenyl(92-52-4) | [EPA Substance Registry System]
92-52-4(EPA Substance) |
| Hazard Information | Back Directory | [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 fl ui | [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. | [Reactivity Profile]
BIPHENYL(92-52-4) is incompatible with oxidizers. | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
CALL FOR MEDICAL AID. VAPOR, MIST OR DUST: Irritating to eyes, nose, throat and skin. Flush affected area with plenty of water. IF IN EYES, hold eyelids open and flush with plenty of water. SOLID OR LIQUID: Irritating to skin and eyes, nose and throat. Remove contaminated clothing and shoes. Flush affected areas with plenty water. IF IN EYES, hold eyelids open and flush with plenty of water. If swallowed, do not induce vomiting. Harmful if inhaled or swallowed. Causes irritation to eyes, skin and mucous membrane and upper respiratory tract. Causes central nervous system depression, paralysis and convulsion in animals. May cause headache, diffuse gastrointestinal pain, nausea, indigestion, numbness and aching of limbs, and general fatigue. Liver function test may show abnormalities. Chronic exposure is mostly characterized by central nervous system symptoms, fatigue, headache, tremor, insomnia, sensory impairment, and mood changes. Such symptoms are rare however. | [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 | [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. | [Fire Hazard]
Combustible. Emits toxic fumes under fire conditions. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way valve
or other proper respiratory medical device. Administer oxygen
if breathing is difficult. Remove and isolate contaminated
clothing and shoes. In case of contact with substance,
immediately flush skin or eyes with running water for at
least 20 minutes. For minor skin contact, avoid spreading
material on unaffected skin. Keep victim warm and quiet.
Effects of exposure (inhalation, ingestion or skin contact) to
substance may be delayed. Ensure that medical personnel
are aware of the material(s) involved and take precautions to
protect themselves. Medical observation is recommended
for 24 to 48 hours after breathing overexposure, as pulmonary
edema may be delayed. As first aid for pulmonary
edema, a doctor or authorized paramedic may consider
administering a drug or other inhalation therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1—Poisonous materials, Technical
Name Required. | [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. | [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). | [Application]
Biphenyl is an important organic raw material, which is widely used in medicine, pesticide, dye, liquid crystal materials and other fields. It can be used to synthesize plasticizers and preservatives, and can also be used to manufacture fuels, engineering plastics and high-energy fuels. Biphenyls are found in coal tar, crude oil and natural gas. The preparation methods of biphenyl include chemical synthesis of biphenyl by pyrolysis of benzene and separation and extraction of biphenyl from various coal tar oil fractions. The mass fraction of biphenyl in coal tar is 0.20% - 0.40%. Coal tar extraction and chemical synthesis coexist. Biphenyl is combustible. In case of high temperature, open fire and oxidant, it is dangerous to burn. It should be stored in a cool and ventilated warehouse away from kindling and heat source. It should be stored separately from oxidants and strong acids. It should be loaded and unloaded gently to keep the package intact. Biphenyl is used as heat exchanger and impregnator of fruit packaging paper. Biphenyl can be used in organic synthesis. Biphenyl is the raw material of engineering plastics polysulfone. It is used to prepare Trichlorobenzene and pentachlorophenyl. Biphenyl is used as heat carrier, preservative, dye and so on. Biphenyl is used as a reference material for chromatographic analysis. Biphenyl is the intermediate of rodenticides rodenticide modek and bromadine, and it is an organic carrier with good performance. | [Definition]
An organic compound having a structure
in which two phenyl groups are joined by a
C–C bond. | [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. | [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 | [Flammability and Explosibility]
Nonflammable | [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 | [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. | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N,Xn,F,T | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R62:Possible risk of impaired fertility.
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R11:Highly Flammable.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37:Wear suitable protective clothing and gloves .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S16:Keep away from sources of ignition-No smoking .
S9:Keep container in a well-ventilated place .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
2
| [RTECS ]
DU8050000
| [Autoignition Temperature]
570 °C | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29029030 | [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. | [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 | [Hazardous Substances Data]
92-52-4(Hazardous Substances Data) | [IDLA]
100 mg/m3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ethanol-->Sodium-->Benzene-->Bromobenzene-->COAL TAR-->Polishing oil | [Preparation Products]
Naphthalene-->6-BROMO-4-CHLOROQUINOLINE-->Bromadiolone-->2-Methyl-3-biphenylmethanol-->fluorescent whitening agent ATS-X-->2-Phenylphenol-->β-Estradiol-->4-Aminobiphenyl-->α-phenyl-2-p-tolylethylamine-->2-Phenylindole-->p-Terphenyl-->6-bromoquinolin-4(3H)-one-->4-Biphenylcarboxylic acid-->4-Phenylphenol-->6-CHLORO-2-(CHLOROMETHYL)-3-OXIDO-4-PHENYL-QUINAZOLINE-->brotianide-->3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol-->4-Bromobiphenyl-->2-(2-AMINO-4-BIPHENYL)PROPIONITRILE-->Bitertanol-->polyquinoxaline-->4-BENZYLBIPHENYL-->Raloxifene-->4-(chlorophenylmethyl)-1,1'-biphenyl-->4-Acetylbiphenyl-->3-[1,1'-Biphenyl]-4-yl-1,2,3,4-tetrahydro-1-naphthol-->4-BIPHENYLSULFONYL CHLORIDE-->4,4'-Bis(bromomethyl)biphenyl-->4,4'-Bis(chloromethyl)-1,1'-biphenyl-->4,4'-Diacetylbiphenyl-->Bifonazole-->4-Benzoylbiphenyl-->Fenbufen |
| Questions And Answer | Back Directory | [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]
Biphenyls are low toxic and irritating to humans. Its steam can stimulate eyes, nose and trachea, cause loss of appetite and vomiting, and has certain toxicity to the nervous system, digestive system and kidney. The oral LD50 of rats was 3.28g/kg. The maximum allowable concentration in the workplace is > 1mg / m3 (coexisting with diphenyl ether). It can stimulate, damage the heart, liver and kidney, and have toxic effects on the reproductive system of humans and other animals. This product has stimulating effect and damages myocardium, liver and kidney. LD50: 3280mg / kg in rats (25% olive oil solution) and 240mg / kg in rabbits. It exists in flue-cured tobacco, oriental tobacco and flue gas. | [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. | [Preparation]
High temperature coal tar contains about 3.0% biphenyl, which can be recovered from washing oil fraction. In 1926, Dow Chemical Company of the United States began to produce biphenyl by pyrolysis of benzene. Another source of biphenyl is the by-product of thermal dealkylation of toluene to benzene. With the development of this process, the byproduct biphenyl of this process has gradually become the main source of biphenyl. In the laboratory, the diazonium salt obtained by diazotization of aniline is added to benzene, and then the mixture is slowly added to sodium hydroxide solution, stirred for reaction, and the temperature slowly rises from below 5 ℃ to 30-35 ℃. Biphenyl is formed after reaction for 8 hours. |
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