2-Phenylethyl bromide

2-Phenylethyl bromide

Names
Preferred IUPAC name (2-Bromoethyl)benzene
Other names Phenethyl bromide
Identifiers
CAS Number	103-63-9  Y
3D model (JSmol)	Interactive image
ChemSpider	7383  Y
ECHA InfoCard	100.002.846
PubChem CID	7666
UNII	96O442668X  Y
CompTox Dashboard (EPA)	DTXSID1033876
InChI InChI=1S/C8H9Br/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2 Y Key: WMPPDTMATNBGJN-UHFFFAOYSA-N Y InChI=1/C8H9Br/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2 Key: WMPPDTMATNBGJN-UHFFFAOYAQ
SMILES BrCCc1ccccc1
Properties
Chemical formula	C8H9Br
Molar mass	185.064 g·mol−1
Appearance	Colorless liquid
Density	1.355 g/cm3
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 [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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. ^[1]

Upon reaction with hydrazine, phenelzine is produced.

It can be used to produce fentanyl and is on the Special Surveillance List of the DEA. ^[2]

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   978-3-527-30673-2.
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.