Benzyl bromide

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Benzyl bromide[1]
Skeletal structure of the benzyl bromide molecule
3D structure of the benzyl bromide molecule
Preferred IUPAC name
Other names
Benzyl bromide
3D model (Jmol)
ECHA InfoCard 100.002.589
Molar mass 171.04 g·mol−1
Appearance colorless liquid
Odor very sharp and pungent
Density 1.438 g/cm3
Melting point −3.9 °C (25.0 °F; 269.2 K)
Boiling point 201 °C (394 °F; 474 K)
Solubility soluble in benzene, CCl4
miscible in ethanol, ether
Flash point 70 °C (158 °F; 343 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox 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 in chemical warfare, both in actual combat and in training due to its irritating yet non-lethal nature.


Benzyl bromide can be synthesized by the bromination of toluene under conditions suitable for a free radical halogenation:

Darstellung Benzylbromid.svg

N-Bromosuccinimide may also be used in place of elemental bromine.

See also[edit]


  1. ^ Merck Index (11th ed.). p. 1142.