Bromobenzene

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Bromobenzene
Structure of bromobenzene
Space-filling model of bromobenzene
Names
Preferred IUPAC name
Bromobenzene[1]
Other names
Phenyl Bromide
Bromobenzol
Monobromobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.295
KEGG
RTECS number CY9000000
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 1.124 cP (20 °C)
Hazards
Irritant Xi Dangerous for the Environment (Nature) N
R-phrases (outdated) R10, R38, R51/53
S-phrases (outdated) (S2), S61
NFPA 704
Flammability code 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 fuelHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 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 ☑Y☒N ?)
Infobox references

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

Synthesis and reactions[edit]

Bromobenzene is prepared by the action of bromine on benzene in the presence of Lewis acid catalysts such as ferric bromide.

Bromobenzene is used to introduce a phenyl groups 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.[2] Other methods involve palladium-catalyzed coupling reactions such as the Suzuki reaction. Bromobenzene is used as a precursor in the manufacture of phencyclidine.

Toxicity[edit]

Animal tests indicate low toxicity.[3] Little is known about chronic effects.[4][5]

For liver toxicity, the 3,4-epoxide are proposed intermediates.[6]

See also[edit]

References[edit]

  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. ^ G. S. Hiers (1927). "Triphenylstibine". Org. Synth. 7: 80. doi:10.15227/orgsyn.007.0080.CS1 maint: Uses authors parameter (link)
  3. ^ e.V., Deutsche Gesetzliche Unfallversicherung. "IFA - Databases on hazardous substance (GESTIS): GESTIS database on hazardous substances". www.dguv.de. Retrieved 2018-03-29.
  4. ^ Szymańska, J. A.; Piotrowski, J. K. (November 2000). "Hepatotoxicity of monobromobenzene and hexabromobenzene: effects of repeated dosage in rats". Chemosphere. 41 (10): 1689–1696. ISSN 0045-6535. PMID 11057697.
  5. ^ Council, National Research (1977-01-01). Drinking Water and Health,: Volume 1. p. 693. doi:10.17226/1780. ISBN 9780309026192.
  6. ^ Integrated Risk Information System, U.S. Environmental Protection Agency. "TOXICOLOGICAL REVIEW OF BROMOBENZENE" (PDF). U.S. Environmental Protection Agency.