Phenacyl bromide

Phenacyl bromide
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2-Bromo-1-phenylethan-1-one
Other names
2-Bromo-1-phenylethanone
2-Bromoacetophenone
α-Bromoacetophenone
Bromomethyl phenyl ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.659 Edit this at Wikidata
UNII
  • InChI=1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 checkY
    Key: LIGACIXOYTUXAW-UHFFFAOYSA-N checkY
  • InChI=1/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
    Key: LIGACIXOYTUXAW-UHFFFAOYAV
  • O=C(c1ccccc1)CBr
Properties
C8H7BrO
Molar mass 199.047 g·mol−1
Appearance Colorless solid
Melting point 50 °C (122 °F; 323 K)[1]
Boiling point 136 °C (277 °F; 409 K) 18 mm Hg[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic(T)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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. ^ a b Phenacyl Bromide, TCI America
  2. ^ R. M. Cowper and L. H. Davidson. "Phenacyl bromide". Organic Syntheses; Collected Volumes, vol. 2, p. 480.
  3. ^ A. Emmerling and C. Engler (1871). "Ueber einige Abkömmlinge des Acetophenons". Ber. 4 (1): 147–149. doi:10.1002/cber.18710040149.


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