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249440

Sigma-Aldrich

Hydrocinnamoyl chloride

98%

Synonym(s):

3-Phenylpropionyl chloride

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About This Item

Linear Formula:
C6H5CH2CH2COCl
CAS Number:
645-45-4
Molecular Weight:
168.62
Beilstein:
742586
EC Number:
211-443-6
MDL number:
MFCD00000748
UNSPSC Code:
12352100
PubChem Substance ID:
24854993
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.5265 (lit.)

bp

107 °C/11 mmHg (lit.)

mp

−7-−5 °C (lit.)

density

1.135 g/mL at 25 °C (lit.)

functional group

acyl chloride
phenyl

SMILES string

ClC(=O)CCc1ccccc1

InChI

1S/C9H9ClO/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

InChI key

MFEILWXBDBCWKF-UHFFFAOYSA-N

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General description

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

Application

Hydrocinnamoyl chloride has been used in:
  • enantioselective synthesis of the antifouling agent, (+)-maculalactone A
  • synthesis of hydrocinnamoyl-farnesyl-L-cysteine methyl ester

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H315,H331,H412

Hazard Classifications

Acute Tox. 3 Inhalation - Aquatic Chronic 3 - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBF5666V
STBD0575V
STBB3456V
STBB8993V
STBB3456

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Electrochemical reduction of phenylacetyl chloride and hydrocinnamoyl chloride at mercury cathodes in acetonitrile.
Mubarak MS, et al.
Journal of Electroanalytical Chemistry, 350(1), 205-216 (1993)
Onovughode T Oboh et al.
Journal of biochemical and molecular toxicology, 22(1), 51-62 (2008-02-15)
The C-terminal --COOH of prenylated proteins is methylated to --COOCH3. The --COOCH3 ester forms are hydrolyzed by prenylated methylated protein methyl esterase (PMPMEase) to the original acid forms. This is the only reversible step of the prenylation pathway. PMPMEase has
Richard J Duffy et al.
The Journal of organic chemistry, 74(13), 4772-4781 (2009-05-21)
A novel class of small spirocyclic heterocycles, spiroepoxy-beta-lactones (1,4-dioxaspiro[2.3]-hexan-5-ones), is described that exhibit a number of interesting reactivity patterns. These spiroheterocycles, including an optically active series, are readily synthesized by epoxidation of ketene dimers (4-alkylidene-2-oxetanones) available from homo- or heteroketene
Abbas D Farahani et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 20(7), 972-983 (2019-02-21)
To investigate the role of the capping group in the solution and solid-state self-assembly of short peptide amphiphiles, dialanine and diphenylalanine have been linked via the N-terminus to a benzene (phenyl) and 3-naphthyl capping groups using three different methylene linkers;

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