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Bromobenzene

Bromobenzene
Structure of bromobenzene
Space-filling model of bromobenzene
Names
Preferred IUPAC name
Bromobenzene
Other names
Phenyl Bromide;
Bromobenzol;
Monobromobenzene
Identifiers
108-86-1 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:3179 YesY
ChEMBL ChEMBL16068 YesY
ChemSpider 7673 YesY
ECHA InfoCard 100.003.295
KEGG C11036 YesY
PubChem 7961
RTECS number CY9000000
Properties
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
-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 R10, R38, R51/53
S-phrases (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 fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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  (what is YesYN ?)
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. The term bromobenzenes may occasionally be used to refer to a benzene containing any number of bromine atoms, or with additional substituents.

Bromobenzene is prepared industrially by the action of bromine on benzene in the presence of iron powder.

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.

It is a toxic substance and can cause liver and nervous system damage if inhaled, ingested, or absorbed through the skin.


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