1137. Benzylideneacetone

Nomenclature

CAS number: 122-57-6; 1896-62-4 ((E)-form) ; 937-53-1 ((Z)-form)
4-Phenyl-3-buten-2-one; acetocinnamone; benzalacetone; cinnamyl methyl ketone; methyl styryl ketone.
C10H10O; mol wt 146.19.
C 82.16%, H 6.89%, O 10.94%.

Description and references

Prepn from acetone and benzaldehyde: L. Claisen, A. Claparede, Ber. 14, 2460 (1881); K. V. Auwers, ibid. 45, 2764 (1912); N. L. Drake, P. Allen, Jr., Org. Synth. 3, 17 (1923). Purification by steam distillation: Fromm, Haas, Ann. 394, 291 (1912). Absorption spectrum: F. Baker, J. Chem. Soc., Trans. 91, 1490 (1907) DOI; E. C. C. Baly, K. Schafer, ibid. 93, 1808 (1908) DOI. Prepn of isomers: G. Gamboni et al., Helv. Chim. Acta 38, 255 (1955) DOI.

Chemical structure

Properties

Lustrous plates on vacuum distillation. Coumarin type odor; sweet, pungent taste. Irritant. mp 41.5°. d1515 1.0377; d445.2 1.0097. bp760 261°; bp200 211°; bp100 187.8°; bp40 161.3°; bp20 143.8°; bp10 127.4°; bp5 112.2°; bp1.0 81.7°. nD45.9 1.5836. Freely sol in alcohol, benzene, chloroform, ether; sparingly sol in water, petr ether.

Use

In perfumery; as flavoring agent. Reagent in organic syntheses.