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Sigma-Aldrich

Cinnamyl chloride

95%

Synonym(s):

(3-Chloropropenyl)benzene

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About This Item

Linear Formula:
C6H5CH=CHCH2Cl
CAS Number:
2687-12-9
Molecular Weight:
152.62
EC Number:
220-246-4
MDL number:
MFCD00000986
UNSPSC Code:
12352100
PubChem Substance ID:
24851258
NACRES:
NA.22

Quality Level

100

assay

95%

form

liquid

refractive index

n20/D 1.584 (lit.)

bp

108 °C/12 mmHg (lit.)

mp

−19 °C (lit.)

density

1.096 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC\C=C\c1ccccc1

InChI

1S/C9H9Cl/c10-8-4-7-9-5-2-1-3-6-9/h1-7H,8H2/b7-4+

InChI key

IWTYTFSSTWXZFU-QPJJXVBHSA-N

General description

Cinnamyl chloride reacts regioselectively with aryl and alkenylgold(I) phosphanes in the presence of palladium catalyst in THF to afford the α-substitution product†.

Application

Cinnamyl chloride was used in the enantioselective total synthesis of helioporins C and E, bioactive marine diterpenes.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Muta. 2 - Repr. 2 - Skin Irrit. 2 - Skin Sens. 1B - STOT RE 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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Juan Carlos Rueda et al.
Polymers, 12(6) (2020-06-26)
Stiff thermosensitive hydrogels (HG) were synthesized by self-crosslinking free radical polymerization of N,N-dimethylacrylamide (DMAA) and N-isopropylacrylamide (NIPAAm), adjusting the degree of swelling by carboxylate-containing sodium acrylate (NaAc) or a 2-oxazoline macromonomer (MM). The formation of hydrogels was possible due to
Wibke Lölsberg et al.
Organic letters, 14(23), 5996-5999 (2012-11-15)
A short and enantioselective total synthesis of helioporins C and E, which are bioactive marine diterpenes containing a serrulatane or amphilectane skeleton, was elaborated. The chirogenic step, i.e. a Cu(I)-catalyzed allylic alkylation of a cinnamyl chloride with methylmagnesium bromide, proceeded
Miguel Peña-López et al.
Organic & biomolecular chemistry, 10(8), 1686-1694 (2012-01-24)
Aryl and alkenylgold(I) phosphanes react regioselectively with allylic electrophiles such as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction

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