Chemistry:Bromobenzene
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| Names | |||
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| Preferred IUPAC name
Bromobenzene[1] | |||
| Other names
Phenyl Bromide
Bromobenzol Monobromobenzene | |||
| Identifiers | |||
3D model (JSmol)
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| 1236661 | |||
| ChEBI | |||
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PubChem CID
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| 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 | |||
Refractive index (nD)
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1.5602 | ||
| Viscosity |
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| Hazards | |||
| GHS pictograms |   
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| GHS Signal word | Warning | ||
| H226, H315, H411 | |||
| P210, P233, P240, P241, P242, P243, P264, P273, P280, P302+352, P303+361+353, P321, P332+313, P362, P370+378, P391, P403+235, P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 51 °C (124 °F; 324 K) | ||
| 565 °C (1,049 °F; 838 K) | |||
| Related compounds | |||
Related halobenzenes
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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   ?)
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| Infobox references | |||
Bromobenzene is the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is C
6H
5Br. 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" (in EN). http://www.dguv.de/ifa/gestis/gestis-stoffdatenbank/index-2.jsp.
- ↑ Szymańska, J. A.; Piotrowski, J. K. (November 2000). "Hepatotoxicity of monobromobenzene and hexabromobenzene: effects of repeated dosage in rats". Chemosphere 41 (10): 1689–1696. doi:10.1016/s0045-6535(00)00064-3. ISSN 0045-6535. PMID 11057697. Bibcode: 2000Chmsp..41.1689S.
- ↑ National Research Council (1977) (in en). Drinking Water and Health: Volume 1. pp. 693. doi:10.17226/1780. ISBN 9780309026192. https://archive.org/details/drinkingwaterhea00asse.
- ↑ "TOXICOLOGICAL REVIEW OF BROMOBENZENE". U.S. Environmental Protection Agency. https://cfpub.epa.gov/ncea/iris/iris_documents/documents/toxreviews/1020tr.pdf.
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