Bromobenzene

Bromobenzene is an aryl halide, C6H5Br. It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis.

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
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, benzene
miscible in chloroform, benzene
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 diamond
2
2
0
Flash point 51 °C (124 °F; 324 K)
565 °C (1,049 °F; 838 K)
Related compounds
Related Halogenobenzenes
 Fluorobenzene
Chlorobenzene
Iodobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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 are proposed intermediates.[8]

See also

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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