2301. Cinnamoyl Chloride

Nomenclature

CAS number: 102-92-1
3-Phenyl-2-propenoyl chloride; benzylideneacetyl chloride; cinnamic acid chloride; 3-phenylacryloyl chloride.
C9H7ClO; mol wt 166.60.
C 64.88%, H 4.24%, Cl 21.28%, O 9.60%.

Description and references

Prepn from cinnamic acid: L. Claisen, P. J. Antweiler, Ber. 13, 2123 (1880); from sodium cinnamate: R. Adams, L. H. Ulich, J. Am. Chem. Soc. 42, 599 (1920). Commercial product is predominately the (2E)-form.

Chemical structure

Derivative

(2E)-Form.

Nomenclature

CAS number: 17082-09-6
trans-Cinnamoyl chloride.

Properties

Yellowish crystals. mp 35-36°; bp58 170-171°; bp25 154°; bp16 147°; bp2 101°; d445.3 1.1617; nD42.5 1.614. Corrosive. Moisture sensitive. Hydrolyzes upon contact with water.

Use

Titrimetric determination of small amts of water. Reagent in organic synthesis.