NIOSH REL: TWA 0.2 ppm, IDLH 100 mg/m3; OSHA PEL: TWA
0.2 ppm; ACGIH TLV: TWA 0.2 ppm.
LogP：
4.008 at 25℃
物理描述：
Biphenyl appears as 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.
颜色/状态：
White scales
气味：
Pleasant, peculiar odor
蒸汽密度：
5.31 (USCG, 1999) (Relative to Air)
蒸汽压力：
8.93X10-3 mm Hg at 25 °C
亨利常数：
3.08e-04 atm-m3/mole
大气OH速率常数：
7.20e-12 cm3/molecule*sec
稳定性/保质期：
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<b><p>请注意：此物品易燃，请远离火源。</p></b>
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自燃温度：
540 °C
分解：
This substance decomposes on heating producing toxic gases, acrid smokes and fumes.
粘度：
0.98 cSt at 100 °C
燃烧热：
624.3 kJ/mol
汽化热：
397.0 J/g at 100 °C
电离电位：
7.95 eV
气味阈值：
low 0.0062 mg/cu m, high 0.3 mg/cu m
折光率：
Index of refraction: 1.475 @ 20 °C/D; 1.588 @ 75 °C/D
After rabbits ingested biphenyl... 64%... was accounted for in the urine primarily as the corresponding glucosiduronic acid and smaller amt of phenols and ether sulfates. From the urine, 4-hydroxybiphenyl, and 4-biphenyl glucosiduronic acid were isolated. ...Liver microsomal preparations from New Zealand White rabbits converted biphenyl into 2- and 4-hydroxybiphenyl. ...Other studies... /noted/ that the 4-isomer and practically no 2-isomer were found. ...The extent of 4-hydroxylation varies with species being poor in cat and trout high in mouse and coypus /(nutria)/. Ability to form 2-hydroxybiphenyl is almost absent in livers of adult rabbits and rats, guinea pigs, hens, trout and fox. Livers of mice, hamsters, cats, coypus, frogs, and young rabbits and rats form measurable amount of the 2-isomer ... .
Biphenyl ... was monohydroxylated by hamster-liver microsomes at positions 2 (minor) & 4; small quantities of 2,2'- & 4,4'-dihydroxybiphenyl were also tentatively identified.
It is metabolized in rat to 4-hydroxybiphenyl (30% of dose) & its glucuronide (20%), 4,4'- & 3,4-dihydroxybiphenyls (5% & 3% respectively) & 4-phenylphenylmercapturic acid (1.3%). Principal metabolite in rabbit, dog & mouse is also 4-hydroxybiphenyl, but mouse also excretes 2-hydroxybiphenyl in urine.
来源:Hazardous Substances Data Bank (HSDB)
代谢
苯巴比妥型诱导剂增加4-羟基联苯的形成，而3-甲基胆蒽型诱导剂增加2-羟基联苯的形成。
Phenobarbital type inducers increase 4-hydroxy biphenyl formation & 3-methylcholanthrene type inducers increase 2-hydroxy biphenyl formation.
Diphenyl is well absorbed through the gastrointestinal tract. It is rapidly metabolized to 4-hydroxybiphenyl, 4-phenyl-catechol and 4,4'-dihydroxyphenyl, which are excreted in urine and bile as glucuronide and mercapturic conjugates. The metabolites of diphenyl, mainly 4-hydroxybiphenyl, are excreted rapidly and almost exclusively in the urine. Acute oral toxicity is moderate. (T48, A588).
IDENTIFICATION: Biphenyl is an aromatic hydrocarbon and it is a colorless solid at room temperature. It is used as an intermediate in the production of a variety of compounds such as: emulsifiers, optical brighteners, crop protection products and plastics, as a dyestuff carrier in textiles and copying paper, as a solvent in pharmaceutical production and in the preservation of citrus fruits. Biphenyl occurs naturally in coal tar, crude oil and natural gas. HUMAN EXPOSURE: Exposure to high levels of biphenyl vapors or dusts in the workplace results in the irritation of the eyes and inflammation of the respiratory tract. Long-term exposure for several years to high level biphenyl concentrations caused damage to the liver and persistent neuronal changes. Direct skin contact may have played a part, in addition to uptake through the respiratory tract. ANIMAL/PLANT STUDIES: Biphenyl was well absorbed through the gastrointestinal tract. In those species examined, the metabolites of biphenyl, mainly 4-hydroxybiphenyl, are excreted rapidly and almost exclusively in the urine. Acute oral toxicity is moderate. It is non-irritating to the skin and only slightly irritating to the eyes. There is no evidence of dermal sensitization. Subchronic exposure by inhalation caused bronchopulmonary changes, whereas long term toxicity studies following inhalation were not identified in literature. In toxicological studies in which rodents have been administered diets containing biphenyl for various periods of time, effects on the urinary system have often been reported. A marked increase of formation of calculi, hyperplasia and desquamation effects have been observed in the urinary tract of male rats administered diets containing biphenyl. An increase in the occurrence of calculi and squamous metaplasia within the urinary bladder of female rats has also been observed, but at lower incidence than males. In male mice fed a diet containing biphenyl developed simple hyperplasia and popular or nodular dysplasia of the urinary bladder. Effects on blood chemistry and hematological parameters have also been observed in animals administered biphenyl orally; these effects occur in male and female rats and mice at intakes over those associated with the development of effects in the urinary bladder of male rats administered biphenyl. For non-neoplastic effects the lowest observed level (LOEL) was based on the development of alterations in hematological parameters (i.e. decreased hemoglobin concentration and hematocrit) in rats fed diets containing biphenyl. In vitro studies with bacteria provided no evidence of mutagenic potential for biphenyl with Saccharomyces cerevisiae D7, gene mutation and mitotic recombination were observed with or without metabolic activation. However, genetic toxicology testing in mammalian cells produced positive results in the presence of metabolic activation and negative results in the absence of metabolic activation. In female mice there were slight increased incidences of benign and malignant liver tumors in animals receiving biphenyl in the diet for 2 yr. An increased incidence of bladder tumors was observed in male rats, but not in female rats or male or female mice, administered high levels of biphenyl. However, observations of an increased incidence of histopathological effects and the formation of calculi within the urinary bladder, in absence of bladder tumors in female rats administered biphenyl for 2 yr, lack of data identifying a direct association between calculi formation, regenerative hyperplasia of the urothelium, and the development of bladder tumors within individual male animals and (3) the potential genotoxicity of biphenyl could suggest that the development of bladder tumors in the male rats may not have been entirely due to the effects associated with the formation of calculi within the urinary bladder. This observation and the hepatocarcinogenicity in female mice raises some concerns with respect to the carcinogenicity of biphenyl. Available data on the reproductive toxicity of biphenyl are limited. Results from a 3 generation study in rats, in which adverse effects such as decreased fertility, litter size, growth rate were noted, there was no evidence that biphenyl induced reproductive or developmental effects. Biphenyl has weak bactericidal and fungistatic properties. In toxicity studies on organisms of four trophic levels, the lowest no observed effect concentration (NOEC) was reported for the most sensitive species, Daphnia magna.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
毒性总结
联苯改变了线粒体膜的渗透性特性（A279）。
Biphenyl alters the permeability properties of mitochondrial membranes (A279).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
致癌性证据
癌症分类：D组 不可归入人类致癌性类别
Cancer Classification: Group D Not Classifiable as to Human Carcinogenicity
CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: No human data and inadequate studies in mice and rats. Results of genotoxicity tests are generally negative. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Inadequate.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌物分类
无致癌性迹象（未被国际癌症研究机构IARC列名）。
No indication of carcinogenicity (not listed by IARC). (L135)
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.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
上联：一年四季春常在；下联：万紫千红永开花；横批：喜迎新春。
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.
1.周国泰，化学危险品安全技术全书，化学工业出版社，1997 2.国家环保局有毒化学品管理办公室、北京化工研究院合编，化学品毒性法规环境数据手册，中国环境科学出版社.1992 3.Canadian Centre for Occupational Health and Safety,CHEMINFO Database.1998 4.Canadian Centre for Occupational Health and Safety, RTECS Database, 1989
Reactions of organometallic compounds, catalyzed by transition metal complexes. 7. Oxidative demercuration of arylmercury in the presence of complexes of palladium and rhodium
Nickel(II) N‐Heterocyclic Carbene Complexes: Versatile Catalysts for C–C, C–S and C–N Coupling Reactions
作者：Lourdes Benítez Junquera、Francys E. Fernández、M. Carmen Puerta、Pedro Valerga
DOI：10.1002/ejic.201700057
日期：2017.5.18
A variety of Ni(II) complexes with a wide range of electronic and steric properties, bearing picolyl-imidazolidene ligands (a-g) and Cp (2a-f) or Cp* (3a,c,g) groups, have been synthesised and characterised using NMR and single crystal X-ray crystallography. The complexes have been used as precatalysts for a wide range of catalytic transformations most likely involving a Ni0/NiII catalytic cycle. In
The nickel-catalyzed reductive cleavage of esters in the absence of an external reductant, which involves the cleavage of an inert acyl C–O bond in O-alkyl esters is reported.
Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various
Biphenyl-2-ols undergo regioselectivemono- and diarylation upon a treatment with aryl iodides in the presence of a palladium catalyst in DMF using Cs2CO3 as a base to produce 1,1′ : 2′,1″-terphenyl-2-ol and 2′,6′-diphenylbiphenyl-2-ol and their derivatives. The reaction of 1-naphthol selectively occurs at its 8-position to give 8-aryl-1-naphthols. In the reaction of 2-naphthol with aryl bromides, diarylated
A direct, mild and efficient trifluoromethylation of primary and secondary phosphines is achieved with easily accessible, cheap hypervalent iodine compounds acting as electrophilic CF(3)-transfer reagents.
