Phenacyl bromide

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)
Boiling point	136 °C (277 °F; 409 K) 18 mm Hg
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). verify (what is ?) 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

^ ^a ^b Phenacyl Bromide, TCI America
^ R. M. Cowper and L. H. Davidson. "Phenacyl bromide". Organic Syntheses; Collected Volumes, vol. 2, p. 480.
^ 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

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[TCI-1] 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.

[1]

[2]

[3]

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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51846^Y
ChEMBL	ChEMBL102953^Y
ChemSpider	6023^Y
ECHA InfoCard	100.000.659
PubChem CID	6259
UNII	754Y0U325I^Y
CompTox Dashboard (EPA)	DTXSID2049426
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
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
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). Y verify (what is ^YN ?) Infobox references