Bromobenzene
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| Names | |||
|---|---|---|---|
| IUPAC name
Bromobenzene | |||
| Other names
Phenyl Bromide; Bromobenzol; Monobromobenzene | |||
| Identifiers | |||
108-86-1  | |||
| ChEBI | CHEBI:3179 | ||
| ChEMBL | ChEMBL16068 | ||
| ChemSpider | 7673 | ||
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| Jmol-3D images | Image | ||
| KEGG | C11036 | ||
| PubChem | 7961 | ||
| RTECS number | CY9000000 | ||
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| Properties | |||
| Molecular formula |
C6H5Br | ||
| Molar mass | 157.01 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 | ||
| Refractive index (nD) |
1.5602 | ||
| Viscosity | 1.124 cP (20 °C) | ||
| Hazards | |||
| EU classification |  Xi  N | ||
| R-phrases | R10, R38, R51/53 | ||
| S-phrases | (S2), S61 | ||
| NFPA 704 | |||
| Flash point | 51 °C (124 °F; 324 K) | ||
| 565 °C (1,049 °F; 838 K) | |||
| Related compounds | |||
| Related Halogenobenzenes |
Fluorobenzene Chlorobenzene Iodobenzene | ||
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |||
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| Infobox references | |||
Bromobenzene is an aryl halide, C6H5Br, which can be formed by electrophilic aromatic substitution of benzene using bromine. It is a clear, colourless or pale yellow liquid. It is soluble in methanol and diethyl ether, and very slightly soluble in cold water.[1] The term bromobenzenes may occasionally be used to refer to a benzene containing any number of bromine atoms, or with additional substituents.
Synthesis
Bromobenzene is prepared industrially by the action of bromine on benzene in the presence of iron powder.
Uses
Bromobenzene is used to introduce a phenyl group via palladium-catalyzed coupling reactions such as the Suzuki reaction.
Bromobenzene can be used to prepare the corresponding Grignard reagent, phenylmagnesium bromide. This can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid.
Bromobenzene is used as a precursor in the manufacture of Phencyclidine.
Pharmacology
It is a toxic substance and can cause liver and nervous system damage if inhaled, ingested, or absorbed through the skin.[2]