73. Acetophenone

Nomenclature

CAS number: 98-86-2
1-Phenylethanone; phenyl methyl ketone; acetylbenzene; hypnone.
C8H8O; mol wt 120.15.
C 79.97%, H 6.71%, O 13.32%.

Description and references

Made from benzene and acetylchloride in presence of aluminum chloride; catalytically from acetic and benzoic acids. Prepn from benzene and acetic anhydride: Adams, J. Am. Chem. Soc. 46, 1889 (1924); A. I. Vogel, Practical Organic Chemistry (Longmans, London, 3rd ed., 1959) p 730; Gattermann-Wieland, Die Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 297. Toxicity study: H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol. 30, 63 (1948).

Chemical structure

Properties

Liquid. Forms laminar crystals at low temp. mp 20.5°. d1515 1.033. bp 202°. nD20 1.5339. Flash pt, closed cup: 170.6°F (77°C); open cup: 180°F (82.2°C). Slightly sol in water; freely in alcohol, chloroform, ether, fatty oils, glycerol. Sol in concd H2SO4 with orange color. LD50 orally in rats: 0.90 g/kg (Smyth, Carpenter).

Use

In perfumery to impart an orange-blossom-like odor; catalyst for the polymerization of olefins; in organic syntheses, esp. as photosensitizer.