Benzyl bromide

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Benzyl bromide[1]
Skeletal structure of the benzyl bromide molecule
3D structure of the benzyl bromide molecule
Names
Preferred IUPAC name
(Bromomethyl)benzene
Other names
α-Bromotoluene
Benzyl bromide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.589
UNII
Properties
C7H7Br
Molar mass 171.04 g·mol−1
Appearance colorless liquid
Odor 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 organic solvents
1.5752
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
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).
N verify (what is YesYN ?)
Infobox references

Benzyl bromide is an organic compound with the formula C6H5CH2Br. The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lacrymatory properties. The compound is a reagent for introducing benzyl groups.[2][3]

Synthesis and structure[edit]

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

Darstellung Benzylbromid.svg

The structure has been confirmed by electron diffraction.[4]

Applications[edit]

Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups. The reaction is often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide.[2] In many cases, benzyl serves as protecting group for alcohols and carboxylic acids.[5]

Safety[edit]

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 combat and in training due to its irritating yet non-lethal nature.

See also[edit]

References[edit]

  1. ^ Merck Index (11th ed.). p. 1142. 
  2. ^ a b William E. Bauta (2001). "Benzyl Bromide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb047. 
  3. ^ "Benzyl bromide". Sigma Aldrich. sigmaaldrich.com. Retrieved 8 June 2017. 
  4. ^ Vilkov, L. V.; Sadova, N. I. (March 1976). "Electron diffraction study on the molecular structure of benzyl chloride and benzyl bromide in the vapour phase". Journal of Molecular Structure. 31 (1): 131–142. doi:10.1016/0022-2860(76)80124-X. Retrieved 8 June 2017. 
  5. ^ "Benzyl bromide". chemicalbook.com. Retrieved 8 June 2017.