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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

Signal Word

Warning

Hazard Statements

H315,H317,H341,H361d,H373

Hazard Classifications

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

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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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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