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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.)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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