Phenacyl bromide

Phenacyl bromide
IUPAC name 2-Bromo-1-phenylethanone
Other names 2-Bromoacetophenone; α-Bromoacetophenone; Bromomethyl phenyl ketone
Identifiers
CAS number	70-11-1 Y
PubChem	6259
ChemSpider	6023 Y
ChEBI	CHEBI:51846 Y
ChEMBL	CHEMBL102953 Y
Jmol-3D images	Image 1
SMILES O=C(c1ccccc1)CBr
InChI InChI=1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 Y Key: LIGACIXOYTUXAW-UHFFFAOYSA-N Y InChI=1/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 Key: LIGACIXOYTUXAW-UHFFFAOYAV
Properties
Molecular formula	C8H7BrO
Molar mass	199.04 g mol−1
Appearance	Colorless solid
Melting point	50 °C[1]
Boiling point	136 °C / 18mmHg[1]
Hazards
Main hazards	Toxic(T)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Phenacyl bromide is the organic compound with the formula C₆H₅C(O)CH₂Br. This colourless solid is a powerful lachrymator as well as a useful precursor to other organic compounds.

It is prepared by bromination of acetophenone:^[2]

C₆H₅C(O)CH₃ + Br₂ → C₆H₅C(O)CH₂Br + HBr

The compound was first reported in 1871.^[3]

References

1. ↑ 1.0 1.1 Phenacyl Bromide, TCI America
2. ↑ R. M. Cowper and L. H. Davidson, "Phenacyl bromide", Org. Synth. ; Coll. Vol. 2: 480 
3. ↑ A. Emmerling and C. Engler (1871). "Ueber einige Abkömmlinge des Acetophenons". Ber. 4 (1): 147–149. doi:10.1002/cber.18710040149.