Phenacyl bromide

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.

Phenacyl bromide

Names
Preferred IUPAC name 2-Bromo-1-phenylethan-1-one
Other names 2-Bromo-1-phenylethanone 2-Bromoacetophenone α-Bromoacetophenone Bromomethyl phenyl ketone
Identifiers
CAS Number	70-11-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51846
ChEMBL	ChEMBL102953
ChemSpider	6023
ECHA InfoCard	100.000.659
PubChem CID	6259
UNII	754Y0U325I
CompTox Dashboard (EPA)	DTXSID2049426
InChI InChI=1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 Key: LIGACIXOYTUXAW-UHFFFAOYSA-N InChI=1/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 Key: LIGACIXOYTUXAW-UHFFFAOYAV
SMILES O=C(c1ccccc1)CBr
Properties
Chemical formula	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
Main hazards	Toxic(T)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. Phenacyl Bromide, TCI America
2. R. M. Cowper and L. H. Davidson. "Phenacyl bromide". Organic Syntheses.; Collective Volume, 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.

External links

• Media related to Phenacyl bromide at Wikimedia Commons