Benzyl bromide

Benzyl bromide[1]
IUPAC name Bromomethylbenzene
Identifiers
CAS number	100-39-0 Y
PubChem	7498
ChemSpider	13851576 Y
ChEBI	CHEBI:59858 Y
ChEMBL	CHEMBL1085946 Y
Jmol-3D images	Image 1 Image 2
SMILES BrCc1ccccc1 c1ccc(cc1)CBr
InChI InChI=1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 Y Key: AGEZXYOZHKGVCM-UHFFFAOYSA-N Y InChI=1/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 Key: AGEZXYOZHKGVCM-UHFFFAOYAM
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

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

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

See also

• Benzyl chloride

References