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Benzyl bromide

Benzyl bromide


IUPAC name	Bromomethylbenzene
Identifiers
CAS number	100-39-0
SMILES	BrCC1=CC=CC=C1
Properties
Molecular formula	C₇H₇Br
Molar mass	171.04 g/mol
Density	1.430 g/cm³
Melting point	-3 °C
Boiling point	198-199 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Benzyl bromide, or α-bromotoluene, is an organic compound consisting of a benzene ring substituted with a bromomethyl group. It can be prepared by the bromination of toluene at room temperature in air, using manganese(IV) oxide as a heterogeneous catalyst. It is a colorless liquid that is decomposed slowly in water.

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Benzyl bromide is used in organic synthesis for the introduction of the benzyl protecting group for alcohols and carboxylic acids.

Benzyl bromide is a strong lachrymator and is also intensely irritating to skin and mucous membranes. Because of these properties, it has been used as a war gas.