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Cinnamoyl chloride

Product NameCinnamoyl chloride
CAS102-92-1
MFC9H7ClO
MW166.6
EINECS203-065-5
MOL File102-92-1.mol

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
InChI	1S/C9H7ClO/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6+
InChIKey	WOGITNXCNOTRLK-VOTSOKGWSA-N
SMILES	ClC(=O)\C=C\c1ccccc1
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
TSCA	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29163990
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B

MSDS

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

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

140-10-3

102-92-1

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

Cinnamoyl chloride

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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