2-Phenylethyl bromide is an

organobromide Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon Chemical bond, bonded to bromine. The most pervasive is the naturally produ ...

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 Styrene is an organic compound with the chemical formula C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene is a colorless, oily liquid, although aged samples can appear yellowish. The compound evaporates easi ...

. These conditions lead to anti-

Markovnikov addition In organic chemistry, Markovnikov's rule or Markownikoff's rule describes the outcome of some addition reactions. The rule was formulated by Russian chemist Vladimir Markovnikov in 1870. Explanation The rule states that with the addition of a ...

, giving the 1-bromo derivatives. Upon reaction with hydrazine,

phenelzine Phenelzine, sold under the brand name Nardil among others, is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine family which is primarily used as an antidepressant and anxiolytic to treat depression and a ...

is produced. It can be used to produce

fentanyl Fentanyl is a highly potent synthetic piperidine opioid primarily used as an analgesic (pain medication). It is 30 to 50 times more Potency (pharmacology), potent than heroin and 50 to 100 times more potent than morphine. Its primary Medici ...

and is on the Special Surveillance List of the DEA.

References

{{organohalide-stub Bromoethyl compounds Phenyl compounds