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]

Applications

Some of the known applications of phenacyl bromide include the following list of agents: Levamisole,^[4] Solpecainol,^[5] Fanetizole, Nomifensine, Fendosal (page 170),^[6]^[7]^[8] Trepipam,^[9] Furaprofen, Hexocyclium.^[10]

References

1 2 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.
↑ Raeymaekers, A. H. M., Allewijn, F. T. N., Vandenberk, J., Demoen, P. J. A., Van Offenwert, T. T. T., Janssen, P. A. J. (July 1966). "Novel Broad-Spectrum Anthelmintics. Tetramisole 1 and Related Derivatives of 6-Arylimidazo[2,1-b]thiazole". Journal of Medicinal Chemistry. 9 (4): 545–551. doi:10.1021/jm00322a023.
↑ Berényi, E., Blaskó, G., Nógrádi, M., Petócz, L. (1991). "Solpecainol Hydrochloride < Rec INNM >". Drugs of the Future. 16 (6): 514. doi:10.1358/dof.1991.016.06.140471. ISSN 0377-8282. Retrieved 28 August 2026.
↑ Lednicer, D., Mitscher, L. A. (1984). The organic chemistry of drug synthesis. 3. Wiley. ISBN 9780471092506.
↑ Castañer, J., Arrigoni-Martelli, E. (1976). "Fendosal". Drugs of the Future. 1 (7): 320. doi:10.1358/dof.1976.001.07.68110. ISSN 0377-8282. Retrieved 28 August 2026.
↑ Anderson, V. B., Agnew, M. N., Allen, R. C., Wilker, J. C., Lassman, H. B., Novick, W. J. (February 1976). "Carboxyarylindoles as nonsteroidal antiinflammatory agents". Journal of Medicinal Chemistry. 19 (2): 318–325. doi:10.1021/jm00224a023. Retrieved 28 August 2026.
↑ Hieble, JP; Wilson III, JW; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.
↑ Zaugg, H. E., Michaels, R. J., Glenn, H. J., Swett, L. R., Freifelder, M., Stone, G. R., Weston, A. W. (June 1958). "Tertiary Carbinols of the Piperazine Series. I". Journal of the American Chemical Society. 80 (11): 2763–2768. doi:10.1021/ja01544a047.

External links

Media related to Phenacyl bromide at Wikimedia Commons
Photo of phenacyl bromide crystals

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[TCI-1] 1 2 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.

[4] Raeymaekers, A. H. M., Allewijn, F. T. N., Vandenberk, J., Demoen, P. J. A., Van Offenwert, T. T. T., Janssen, P. A. J. (July 1966). "Novel Broad-Spectrum Anthelmintics. Tetramisole 1 and Related Derivatives of 6-Arylimidazo[2,1-b]thiazole". Journal of Medicinal Chemistry. 9 (4): 545–551. doi:10.1021/jm00322a023.

[5] Berényi, E., Blaskó, G., Nógrádi, M., Petócz, L. (1991). "Solpecainol Hydrochloride < Rec INNM >". Drugs of the Future. 16 (6): 514. doi:10.1358/dof.1991.016.06.140471. ISSN 0377-8282. Retrieved 28 August 2026.

[6] Lednicer, D., Mitscher, L. A. (1984). The organic chemistry of drug synthesis. 3. Wiley. ISBN 9780471092506.

[7] Castañer, J., Arrigoni-Martelli, E. (1976). "Fendosal". Drugs of the Future. 1 (7): 320. doi:10.1358/dof.1976.001.07.68110. ISSN 0377-8282. Retrieved 28 August 2026.

[8] Anderson, V. B., Agnew, M. N., Allen, R. C., Wilker, J. C., Lassman, H. B., Novick, W. J. (February 1976). "Carboxyarylindoles as nonsteroidal antiinflammatory agents". Journal of Medicinal Chemistry. 19 (2): 318–325. doi:10.1021/jm00224a023. Retrieved 28 August 2026.

[9] Hieble, JP; Wilson III, JW; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.

[10] Zaugg, H. E., Michaels, R. J., Glenn, H. J., Swett, L. R., Freifelder, M., Stone, G. R., Weston, A. W. (June 1958). "Tertiary Carbinols of the Piperazine Series. I". Journal of the American Chemical Society. 80 (11): 2763–2768. doi:10.1021/ja01544a047.

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