Bromobenzene

Bromobenzene
Structure of bromobenzene	Space-filling model of bromobenzene
Names
	Preferred IUPAC name Bromobenzene
	Other names Phenyl Bromide; Bromobenzol; Monobromobenzene
Identifiers
CAS Number	108-86-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1236661
ChEBI	CHEBI:3179 ;
ChEMBL	ChEMBL16068 ;
ChemSpider	7673 ;
ECHA InfoCard	100.003.295
EC Number	203-623-8;
KEGG	C11036 ;
PubChem CID	7961;
RTECS number	CY9000000;
UNII	CO4D5J547L;
UN number	2514
CompTox Dashboard (EPA)	DTXSID5024637 ;
	InChI InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H Key: QARVLSVVCXYDNA-UHFFFAOYSA-N ; InChI=1/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H Key: QARVLSVVCXYDNA-UHFFFAOYAB;
	SMILES c1ccc(cc1)Br;
Properties
Chemical formula	C6H5Br
Molar mass	157.010 g·mol−1
Appearance	Colourless liquid
Odor	Pleasant aromatic odor
Density	1.495 g cm−3, liquid
Melting point	−30.8 °C (−23.4 °F; 242.3 K)
Boiling point	156 °C (313 °F; 429 K)
Solubility in water	0.041 g/100 mL
Solubility	soluble in diethyl ether, alcohol, CCl4; miscible in chloroform, benzene, petroleum ether
Vapor pressure	4.18 mm Hg
Magnetic susceptibility (χ)	-78.92·10−6 cm3/mol
Refractive index (nD)	1.5602
Viscosity	1.080 mPa·s at 25 °C; 1.124 mPa·s at 20 °C;
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H411
Precautionary statements	P210, P233, P240, P241, P242, P243, P264, P273, P280, P302+P352, P303+P361+P353, P321, P332+P313, P362, P370+P378, P391, P403+P235, P501
NFPA 704 (fire diamond)	2 2 0
Flash point	51 °C (124 °F; 324 K)
Autoignition; temperature	565 °C (1,049 °F; 838 K)
Related compounds
Related halobenzenes	Fluorobenzene; Chlorobenzene; Iodobenzene
	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

Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is C₆H₅Br. It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis.

Synthesis and reactions

Bromobenzene is prepared by the action of bromine on benzene in the presence of Lewis acid catalysts such as aluminium chloride or ferric bromide.^[3]

Bromobenzene is used to introduce a phenyl group into other compounds. One method involves its conversion to the Grignard reagent, phenylmagnesium bromide. This reagent can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid.^[4] Other methods involve palladium-catalyzed coupling reactions, such as the Suzuki reaction. Bromobenzene is used as a precursor in the manufacture of phencyclidine.

Toxicity

Animal tests indicate low toxicity.^[5] Little is known about chronic effects.^[6]^[7]

For liver toxicity, the 3,4-epoxide is a proposed intermediate.^[8]

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 10, 31. doi:10.1039/9781849733069-00001. ISBN 978-0-85404-182-4.
^ Nayak, Jyoti N.; Aralaguppi, Mrityunjaya I.; Aminabhavi, Tejraj M. (2003). "Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of Ethyl Chloroacetate + Cyclohexanone, + Chlorobenzene, + Bromobenzene, or + Benzyl Alcohol at (298.15, 303.15, and 308.15) K". Journal of Chemical & Engineering Data. 48 (3): 628–631. doi:10.1021/je0201828. ISSN 0021-9568.
^ "Preparation of bromobenzene and iodobenzene". Journal of the Chemical Society, Abstracts. 38: 316. 1880. doi:10.1039/CA8803800307.
^ G. S. Hiers (1927). "Triphenylstibine". Org. Synth. 7: 80. doi:10.15227/orgsyn.007.0080.
^ e.V., Deutsche Gesetzliche Unfallversicherung. "IFA - Databases on hazardous substance (GESTIS): GESTIS database on hazardous substances". www.dguv.de. Retrieved 2018-03-29.
^ Szymańska, J. A.; Piotrowski, J. K. (November 2000). "Hepatotoxicity of monobromobenzene and hexabromobenzene: effects of repeated dosage in rats". Chemosphere. 41 (10): 1689–1696. Bibcode:2000Chmsp..41.1689S. doi:10.1016/s0045-6535(00)00064-3. ISSN 0045-6535. PMID 11057697.
^ National Research Council (1977). Drinking Water and Health: Volume 1. pp. 693. doi:10.17226/1780. ISBN 9780309026192. PMID 25121315.
^ "TOXICOLOGICAL REVIEW OF BROMOBENZENE" (PDF). Integrated Risk Information System. U.S. Environmental Protection Agency.

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 10, 31. doi:10.1039/9781849733069-00001. ISBN 978-0-85404-182-4.

[NayakAralaguppi2003-2] Nayak, Jyoti N.; Aralaguppi, Mrityunjaya I.; Aminabhavi, Tejraj M. (2003). "Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of Ethyl Chloroacetate + Cyclohexanone, + Chlorobenzene, + Bromobenzene, or + Benzyl Alcohol at (298.15, 303.15, and 308.15) K". Journal of Chemical & Engineering Data. 48 (3): 628–631. doi:10.1021/je0201828. ISSN 0021-9568.

[3] "Preparation of bromobenzene and iodobenzene". Journal of the Chemical Society, Abstracts. 38: 316. 1880. doi:10.1039/CA8803800307.

[4] G. S. Hiers (1927). "Triphenylstibine". Org. Synth. 7: 80. doi:10.15227/orgsyn.007.0080.

[5] .V., Deutsche Gesetzliche Unfallversicherung. "IFA - Databases on hazardous substance (GESTIS): GESTIS database on hazardous substances". www.dguv.de. Retrieved 2018-03-29.

[6] Szymańska, J. A.; Piotrowski, J. K. (November 2000). "Hepatotoxicity of monobromobenzene and hexabromobenzene: effects of repeated dosage in rats". Chemosphere. 41 (10): 1689–1696. Bibcode:2000Chmsp..41.1689S. doi:10.1016/s0045-6535(00)00064-3. ISSN 0045-6535. PMID 11057697.

[:6-7] National Research Council (1977). Drinking Water and Health: Volume 1. pp. 693. doi:10.17226/1780. ISBN 9780309026192. PMID 25121315.

[:1-8] "TOXICOLOGICAL REVIEW OF BROMOBENZENE" (PDF). Integrated Risk Information System. U.S. Environmental Protection Agency.

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