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Hydrocinnamoyl chloride

Product NameHydrocinnamoyl chloride
CAS645-45-4
MFC9H9ClO
MW168.62
EINECS211-443-6
MOL File645-45-4.mol

Chemical Properties

Melting point	−7-−5 °C(lit.)
Boiling point	107 °C11 mm Hg(lit.)
Density	1.135 g/mL at 25 °C(lit.)
vapor pressure	6.893Pa at 25℃
refractive index	n20/D 1.5265(lit.)
Flash point	227 °F
storage temp.	Inert atmosphere,2-8°C
solubility	Chloroform (Slightly)
form	Liquid
color	deep greenish-yellow
Water Solubility	Soluble in water (reacts), and ether.
Sensitive	Moisture Sensitive
BRN	742586
InChI	1S/C9H9ClO/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2
InChIKey	MFEILWXBDBCWKF-UHFFFAOYSA-N
SMILES	ClC(=O)CCc1ccccc1
LogP	1.73
CAS DataBase Reference	645-45-4(CAS DataBase Reference)
NIST Chemistry Reference	Benzenepropanoyl chloride(645-45-4)
EPA Substance Registry System	Benzenepropanoyl chloride (645-45-4)

Safety Information

Hazard Codes	C
Risk Statements	20-34-29-14
Safety Statements	26-36/37/39-45-8-30-23
RIDADR	UN 3265 8/PG 2
WGK Germany	3
RTECS	MW5652395
F	10-21
TSCA	TSCA listed
HazardClass	8
PackingGroup	II
HS Code	29163900
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Inhalation Aquatic Chronic 3 Skin Irrit. 2

MSDS

Provider	Language
3-Phenylpropionyl chloride	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

clear colorless to light yellow liquid

Uses

Hydrocinnamoyl chloride has been used in:

enantioselective synthesis of the antifouling agent, (+)-maculalactone A
synthesis of hydrocinnamoyl-farnesyl-L-cysteine methyl ester

Uses

Hydrocinnamoyl chloride is a derivative of phenylpropionic acid used in the preparation of a wide range of pharmaceutical compounds such as antivirals and antitumor agents.

Uses

3-Phenylpropionyl Chloride is a derivative of phenylpropionic acid used in the preparation of a wide range of pharmaceutical compounds such as antivirals and antitumor agents.

General Description

Reduction of hydrocinnamoyl chloride at mercury cathodes in acetonitrile containing tetraalkylammonium perchlorates has been investigated by cyclic voltammetry.

Flammability and Explosibility

Not classified

Synthesis

501-52-0

645-45-4

General procedure for the synthesis of hydrocinnamoyl chloride from hydrogenated cinnamic acid: To a 200 mL flask equipped with a stir bar and an argon inlet septum were added hydrogenated cinnamic acid (5.00 g, 33.3 mmol), N,N-dimethylformamide (DMF, 0.1 mL), and dichloromethane (CH2Cl2, 30 mL). Oxalyl chloride ((COCl)2, 2 M in CH2Cl2, 20.0 mL, 40.0 mmol) was slowly added to the resulting solution over 30 min. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by vacuum concentration to afford 3-phenylpropionyl chloride (74, 5.9 g, yellow oil) in 100% yield. The purity of the product was confirmed to be 99% by high performance liquid chromatography (HPLC) analysis (mobile phase ratio: water:acetonitrile:methanol = 15:10:75) with a retention time of 5.3 min.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2899 - 2903
[2] Patent: WO2013/101911, 2013, A2. Location in patent: Page/Page column 57
[3] Arkivoc, 2018, vol. 2018, # 5, p. 334 - 347
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3825 - 3830
[5] Journal of the American Chemical Society, 1980, vol. 102, # 20, p. 6311 - 6314

Hydrocinnamoyl chloride

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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