Bromobenzene
Structure of bromobenzene
Structure of bromobenzene
Space-filling model of bromobenzene
Space-filling model of bromobenzene
Names
Preferred IUPAC name
Bromobenzene[1]
Other names
Phenyl Bromide
Bromobenzol
Monobromobenzene
Identifiers
3D model (JSmol)
1236661
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.295 Edit this at Wikidata
EC Number
  • 203-623-8
KEGG
RTECS number
  • CY9000000
UNII
  • InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H checkY
    Key: QARVLSVVCXYDNA-UHFFFAOYSA-N checkY
  • InChI=1/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H
    Key: QARVLSVVCXYDNA-UHFFFAOYAB
  • c1ccc(cc1)Br
Properties
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)
0.041 g/100 mL
Solubility soluble in diethyl ether, alcohol, CCl4
miscible in chloroform, benzene, petroleum ether
Vapor pressure 4.18 mm Hg
-78.92·10−6 cm3/mol
1.5602
Viscosity
  • 1.080 mPa·s at 25 °C[2]
  • 1.124 mPa·s at 20 °C
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
Warning
H226, H315, H411
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 51 °C (124 °F; 324 K)
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).
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Bromobenzene is 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

  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.
  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. ^ e.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.
  7. ^ National Research Council (1977). Drinking Water and Health: Volume 1. pp. 693. doi:10.17226/1780. ISBN 9780309026192. PMID 25121315.
  8. ^ "TOXICOLOGICAL REVIEW OF BROMOBENZENE" (PDF). Integrated Risk Information System. U.S. Environmental Protection Agency.
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