Benzyl bromide

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Benzyl bromide
IUPAC name	Bromomethylbenzene
Identifiers
CAS number	[100-39-0]
PubChem	7498
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.

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.

[edit] Synthesis

Benzyl bromide can be synthesized by the bromination of toluene:

[edit] See also

• Benzyl chloride

[edit] References

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