Bromobenzene

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Bromobenzene

IUPAC name Bromobenzene
Other names Phenyl Bromide; Bromobenzol; Monobromobenzene
Identifiers
CAS number	108-86-1^Y
PubChem	7961
ChemSpider	7673^Y
KEGG	C11036^Y
ChEBI	CHEBI:3179^Y
ChEMBL	CHEMBL16068^Y
RTECS number	CY9000000
Jmol-3D images	Image 1
SMILES c1ccc(cc1)Br
InChI InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H^Y Key: QARVLSVVCXYDNA-UHFFFAOYSA-N^Y InChI=1/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H Key: QARVLSVVCXYDNA-UHFFFAOYAB
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
Solubility in water	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 (n_D)	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	2 2 0
Flash point	51 °C; 124 °F; 324 K
Autoignition temperature	565 °C; 1,049 °F; 838 K
Related compounds
Related Halogenobenzenes	Fluorobenzene Chlorobenzene Iodobenzene
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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]

References

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