Benzyl bromide

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Benzyl bromide[1]
Skeletal structure of the benzyl bromide molecule 3D structure of the benzyl bromide molecule
Identifiers
CAS number 100-39-0 YesY
PubChem 7498
ChemSpider 13851576 YesY
ChEBI CHEBI:59858 YesY
ChEMBL CHEMBL1085946 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H7Br
Molar mass 171.03 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
Refractive index (nD) 1.5752
Hazards
Flash point 70 °C (158 °F; 343 K)
Except where noted otherwise, 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 as a war gas.

Synthesis[edit]

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]

References[edit]

  1. ^ Merck Index, 11th Edition, 1142