Biphenyl

Biphenyl
Names
	Preferred IUPAC name 1,1′-Biphenyl
	Other names Biphenyl; Phenylbenzene; Xenene;
Identifiers
CAS Number	92-52-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1634058
ChEBI	CHEBI:17097 ;
ChEMBL	ChEMBL14092 ;
ChemSpider	6828 ;
ECHA InfoCard	100.001.967
EC Number	202-163-5;
E number	E230 (preservatives)
Gmelin Reference	3808
KEGG	C06588 ;
PubChem CID	7095;
RTECS number	DU8050000;
UNII	2L9GJK6MGN ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID4020161 ;
	InChI InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H Key: ZUOUZKKEUPVFJK-UHFFFAOYSA-N ; InChI=1/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H Key: ZUOUZKKEUPVFJK-UHFFFAOYAV;
	SMILES c1ccccc1-c2ccccc2;
Properties
Chemical formula	C12H10
Molar mass	154.212 g·mol−1
Appearance	Colorless to pale-yellow crystals
Odor	pleasant
Density	1.04 g/cm3
Melting point	69.2 °C (156.6 °F; 342.3 K)
Boiling point	255 °C (491 °F; 528 K)
Solubility in water	4.45 mg/L
Vapor pressure	0.005 mmHg (20°C)
Magnetic susceptibility (χ)	−103.25·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H410
Precautionary statements	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)	1 1 0
Flash point	113 °C (235 °F; 386 K)
Autoignition; temperature	540 °C (1,004 °F; 813 K)
Explosive limits	0.6–5.8%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2400 mg/kg (oral, rabbit); 3280 mg/kg (oral, rat); 1900 mg/kg (oral, mouse); 2400 mg/kg (oral, rat)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 1 mg/m3 (0.2 ppm)
REL (Recommended)	TWA 1 mg/m3 (0.2 ppm)
IDLH (Immediate danger)	100 mg/m3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0239". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c ^d ^e ^f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ "Diphenyl". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 4 December 2014. Retrieved 17 March 2015.
^ "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.
^ "Beilsteins Handbuch der organischen Chemie, Volume 5".

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0239". National Institute for Occupational Safety and Health (NIOSH).

[GESTIS-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".

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Names



Preferred IUPAC name 1,1′-Biphenyl
Other names Biphenyl Phenylbenzene Xenene
Identifiers
CAS Number	92-52-4^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1634058
ChEBI	CHEBI:17097^Y
ChEMBL	ChEMBL14092^Y
ChemSpider	6828^Y
ECHA InfoCard	100.001.967
EC Number	202-163-5
E number	E230 (preservatives)
Gmelin Reference	3808
KEGG	C06588^Y
PubChem CID	7095
RTECS number	DU8050000
UNII	2L9GJK6MGN^Y
UN number	3077
CompTox Dashboard (EPA)	DTXSID4020161
InChI InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H^Y Key: ZUOUZKKEUPVFJK-UHFFFAOYSA-N^Y InChI=1/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H Key: ZUOUZKKEUPVFJK-UHFFFAOYAV
SMILES c1ccccc1-c2ccccc2
Properties
Chemical formula	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]
Solubility in water	4.45 mg/L^[2]
Vapor pressure	0.005 mmHg (20°C)^[1]
Magnetic susceptibility (χ)	−103.25·10⁻⁶ cm³/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H410
Precautionary statements	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)	1 1 0
Flash point	113 °C (235 °F; 386 K)^[2]
Autoignition temperature	540 °C (1,004 °F; 813 K)^[2]
Explosive limits	0.6–5.8%^[1]
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	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). N verify (what is ^YN ?) Infobox references