Benzyl bromide
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
(Bromomethyl)benzene | |||
| Other names
α-Bromotoluene Benzyl bromide | |||
| Identifiers | |||
| 3D model (JSmol) |
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.002.589 | ||
| PubChem CID |
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| UNII | |||
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| 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 | ||
| Refractive index (nD) |
1.5752 | ||
| Hazards | |||
| GHS pictograms |  | ||
| 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). | |||
 verify (what is  ?) | |||
| 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
Benzyl bromide can be synthesized by the bromination of toluene under conditions suitable for a free radical halogenation:
The structure has been confirmed by electron diffraction.[4]
Applications
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
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
References
- ↑ Merck Index (11th ed.). p. 1142.
- 1 2 William E. Bauta (2001). "Benzyl Bromide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb047.
- ↑ "Benzyl bromide". Sigma Aldrich. sigmaaldrich.com. Retrieved 8 June 2017.
- ↑ 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.
- ↑ "Benzyl bromide". chemicalbook.com. Retrieved 8 June 2017.