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Merck
CN

249440

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24854993
EC Number:
211-443-6
Beilstein/REAXYS Number:
742586
MDL number:
MFCD00000748
Assay:
98%
Form:
liquid

Key Documents

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form

liquid

assay

98%

SMILES string

ClC(=O)CCc1ccccc1

InChI key

MFEILWXBDBCWKF-UHFFFAOYSA-N

InChI

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

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

Quality Level

100

Related Categories

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBF5666V
STBD0575V
STBB3456V
S63890
STBB8993V

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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
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
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)
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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