Cinnamoyl chloride Chemical Properties

Melting point:

35-37 °C (lit.)

Boiling point:

256-258 °C (lit.)

Density 

d445.3 1.1617

refractive index 

nD42.5 1.614

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

dioxane: 0.1 g/mL, clear

form 

Crystalline Solid

color 

White to yellow

Water Solubility 

DECOMPOSES

Merck 

13,2323

BRN 

606265

CAS DataBase Reference

102-92-1(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenoyl chloride, 3-phenyl-(102-92-1)

EPA Substance Registry System

2-Propenoyl chloride, 3-phenyl- (102-92-1)

Safety Information

Hazard Codes 

C

Risk Statements 

34-29-20-14

Safety Statements 

26-36/37/39-45-25-30-23-8

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

10-21

HazardClass 

8

PackingGroup 

III

HS Code 

29163990

MSDS

• Language:English Provider:3-Phenyl-2-propenoyl chloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Cinnamoyl chloride Usage And Synthesis

Chemical Properties

white to yellowish crystalline solid

Uses

Titrimetric determination of small amounts of water.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 714, 1955
Tetrahedron Letters, 14, p. 5121, 1973 DOI: 10.1016/S0040-4039(01)87403-7

Hazard

Skin irritant.

Synthesis

General procedure for the synthesis of 3-phenyl-2-propenyl chloride from trans-cinnamic acid: trans-cinnamic acid (1.0 mmol) was mixed with excess thionyl chloride (5 mL) and reacted at reflux for 2 hours. After completion of the reaction, the excess thionyl chloride was removed by vacuum concentration to obtain 3-phenyl-2-propenyl chloride in quantitative yield.

Purification Methods

Refractionate it in a vacuum until the distillate solidifies on cooling, and recrystallise it from pet ether. The trans-amide has m 145-150o (from H2O) [Beilstein 9 III 2711]. [Adams & Ulich J Am Chem Soc 42 605 1920, Bergmann et al. J Chem Soc 2524 1952, Beilstein 9 H 587, 9 I 233, 9 II 390, 9 III 2710, 9 IV 2020.]

References

[1] Tetrahedron, 2009, vol. 65, # 42, p. 8690 - 8696
[2] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 673 - 676
[3] Molecules, 2016, vol. 21, # 1,
[4] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748
[5] Patent: WO2007/141389, 2007, A1. Location in patent: Page/Page column 62

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