Benzyl bromide

Benzyl bromide

Chembox new
Name = Benzyl bromide
ImageFileL1 = Benzyl-bromide-skeletal.svg
ImageSizeL1 = 120px
ImageNameL1 = Skeletal structure of the benzyl bromide molecule
ImageFileR1 = Benzyl-bromide-3D-vdW.png ImageSizeR1 = 100px
ImageNameR1 = 3D structure of the benzyl bromide molecule
IUPACName = Bromomethylbenzene
Section1 = Chembox Identifiers
CASNo = 100-39-0
PubChem = 7498
SMILES = BrCC1=CC=CC=C1
Section2 = Chembox Properties
Formula = C7H7Br
MolarMass = 171.04 g/mol
Density = 1.430 g/cm³
MeltingPt = -3 °C
BoilingPt = 198-199 °C

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.

Synthesis

Benzyl bromide can be synthesized by the bromination of toluene:

ee also

*Benzyl chloride

References


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