Biphenyl

For the compound including hydroxyl groups, see Bisphenol.
"Lemonene" redirects here. For the monoterpene in citrus oil, see Limonene.
Biphenyl
Skeletal formula
Space filling model showing its twisted conformation
sample
Names
Preferred IUPAC name
1,1′-Biphenyl
Other names
  • Biphenyl
  • Phenylbenzene
  • Xenene
Identifiers
3D model (JSmol)
3DMet
1634058
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.967 Edit this at Wikidata
EC Number
  • 202-163-5
E number E230 (preservatives)
3808
KEGG
RTECS number
  • DU8050000
UNII
UN number 3077
  • InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H checkY
    Key: ZUOUZKKEUPVFJK-UHFFFAOYSA-N checkY
  • InChI=1/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
    Key: ZUOUZKKEUPVFJK-UHFFFAOYAV
  • c1ccccc1-c2ccccc2
Properties
C12H10
Molar mass 154.212 g·mol−1
Appearance Colorless to pale-yellow crystals
Odor pleasant[1]
Density 1.04 g/cm3[2]
Melting point 69.2 °C (156.6 °F; 342.3 K)[2]
Boiling point 255 °C (491 °F; 528 K)[2]
4.45 mg/L[2]
Vapor pressure 0.005 mmHg (20°C)[1]
−103.25·10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H335, H410
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 113 °C (235 °F; 386 K)[2]
540 °C (1,004 °F; 813 K)[2]
Explosive limits 0.6–5.8%[1]
Lethal dose or concentration (LD, LC):
2400 mg/kg (oral, rabbit)
3280 mg/kg (oral, rat)
1900 mg/kg (oral, mouse)
2400 mg/kg (oral, rat)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 1 mg/m3 (0.2 ppm)[1]
REL (Recommended)
 TWA 1 mg/m3 (0.2 ppm)[1]
IDLH (Immediate danger)
 100 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene[4] or BP) is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen (the site at which it is attached) may use the prefixes xenyl or diphenylyl.[5]

It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula (C6H5)2. It is notable as a starting material for the production of polychlorinated biphenyls (PCBs), which were once widely used as dielectric fluids and heat transfer agents.

Biphenyl is also an intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, and plastics. Biphenyl is insoluble in water, but soluble in typical organic solvents. The biphenyl molecule consists of two connected phenyl rings.

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0239". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ "Diphenyl". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 4 December 2014. Retrieved 17 March 2015.
  4. ^ "Biphenyl". NIST Chemistry WebBook. US National Institute of Standards and Technology. An obscure name, according to "Limonene". Molecule of the Week Archive. American Chemical Society. Nov 1, 2021.
  5. ^ "Beilsteins Handbuch der organischen Chemie, Volume 5".