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2-Phenylethyl bromide

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2-Phenylethyl bromide
Names
Preferred IUPAC name (2-Bromoethyl)benzene
Other names Phenethyl bromide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.846 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H9Br/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2Key: WMPPDTMATNBGJN-UHFFFAOYSA-N
  • InChI=1/C8H9Br/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2Key: WMPPDTMATNBGJN-UHFFFAOYAQ
SMILES
  • BrCCc1ccccc1
Properties
Chemical formula C8H9Br
Molar mass 185.064 g·mol
Appearance Colorless liquid
Density 1.355 g/cm
Melting point −56 °C (−69 °F; 217 K)
Boiling point 221 °C (430 °F; 494 K)
Solubility in water Insoluble in water
Hazards
Flash point 89 °C (192 °F; 362 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Phenylethyl bromide is an organobromide with the formula C6H5CH2CH2Br. It is a colorless liquid, although older samples appear yellow. Analogous to the preparation of most 1-bromoalkanes, it is prepared by free-radical addition of hydrogen bromide to styrene. These conditions lead to anti-Markovnikov addition, giving the 1-bromo derivatives.

Upon reaction with hydrazine, phenelzine is produced.

It can be used to produce fentanyl and is on the Special Surveillance List of the DEA.

References

  1. Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. ISBN 978-3527306732.
  2. "Special Surveillance List of Chemicals, Products, Materials and Equipment Used in the Clandestine Production of Controlled Substances or Listed Chemicals". Archived from the original on April 20, 2011. Retrieved May 20, 2011.


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