187186

Sigma-Aldrich

Cinnamyl chloride

95%

Synonym(s):
(3-Chloropropenyl)benzene
Linear Formula:
C6H5CH=CHCH2Cl
CAS Number:
Molecular Weight:
152.62
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

95%

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.

Packaging

5, 100 g in glass bottle

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T+

Risk Statement

22-26-34-43

Safety Statement

26-28-36/37/39-45

RIDADR

UN 1760 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

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...
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...
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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