7269. Phenylacetone

Nomenclature

CAS number: 103-79-7
1-Phenyl-2-propanone; benzyl methyl ketone.
C9H10O; mol wt 134.18.
C 80.56%, H 7.51%, O 11.92%.

Description and references

Prepn from phenylacetic and acetic acids: R. H. Pickard, J. Kenyon, J. Chem. Soc. 105, 1124 (1914); R. M. Herbst, R. H. Manske, Org. Synth. coll. vol. II, 389 (1943); from α-phenylacetoacetonitrile: P. L. Julian, J. J. Oliver, ibid. 391; from α-methyl-α-phenylethylene oxide: S. Danilow, E. Venus-Danilowa, Ber. 60, 1050 (1927); from diethyl malonate: H. G. Walker, C. R. Hauser, J. Am. Chem. Soc. 68, 1386 (1946). Conformational calculations: M. Hirota et al., Tetrahedron 39, 3091 (1983). Use as prochiral ketone in enantioselective hydrosilylation: H. Brenner et al., Ber. 117, 1330 (1984).

Chemical structure

Properties

Oil, mp -16 to -15°. bp760 214°; bp14 100-101°. d420 1.0157. nD 1.5174. uv max (ethanol): 258, 283 nm (ε 255, 150).

Note

This is a controlled substance: (immediate precursor) 21 CFR, 1308.12.

Use

In organic synthesis; production of benzyl radicals by photolysis.