Benzyl bromide
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
(Bromomethyl)benzene | |||
Other names
α-Bromotoluene
Benzyl bromide | |||
Identifiers | |||
3D model (
JSmol ) |
|||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
|
100.002.589 | ||
IUPHAR/BPS |
|||
PubChem CID
|
|||
UNII | |||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
Properties | |||
C7H7Br | |||
Molar mass | 171.037 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 | ||
log P | 2.92[2] | ||
Refractive index (nD)
|
1.5752 | ||
Hazards | |||
GHS labelling: | |||
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).
|
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 lachrymatory properties. The compound is a reagent for introducing benzyl groups.[3][4]
Synthesis and structure
Benzyl bromide can be synthesized by the bromination of
The structure has been examined by electron diffraction.[5]
Applications
Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive.[6] [7] Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ.[3] In some cases, benzyl serves as protecting group for alcohols and carboxylic acids.[8]
Safety
Benzyl bromide is a strong
See also
References
- ^ Merck Index (11th ed.). p. 1142.
- ^ "Benzyl bromide_msds".
- ^ ISBN 0-471-93623-5.
- Sigma Aldrich. sigmaaldrich.com. Retrieved 8 June 2017.
- .
- .
- .
- ^ "Benzyl bromide". chemicalbook.com. Retrieved 8 June 2017.