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C22369

Sigma-Aldrich

2-Chloroacrylonitrile

98%

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About This Item

Linear Formula:
CH2=CClCN
CAS Number:
920-37-6
Molecular Weight:
87.51
Beilstein:
773744
MDL number:
MFCD00001858
UNSPSC Code:
12352100
PubChem Substance ID:
24892478
NACRES:
NA.22

Quality Level

200

Assay

98%

form

liquid

refractive index

n20/D 1.429 (lit.)

bp

88-89 °C (lit.)

mp

−65 °C (lit.)

density

1.096 g/mL at 25 °C (lit.)

SMILES string

ClC(=C)C#N

InChI

1S/C3H2ClN/c1-3(4)2-5/h1H2

InChI key

OYUNTGBISCIYPW-UHFFFAOYSA-N

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Application

Common reagent in cycloaddition reactions.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Aquatic Acute 1 - Aquatic Chronic 3 - Carc. 1B - Eye Dam. 1 - Flam. Liq. 2 - Resp. Sens. 1 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

42.8 °F - closed cup

Flash Point(C)

6 °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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The Journal of Organic Chemistry, 58, 5200-5200 (1993)
Journal of the Chemical Society. Chemical Communications, 814-814 (1993)
Asymmetric conjugate addition of oxindoles to 2-chloroacrylonitrile: a highly effective organocatalytic strategy for simultaneous construction of 1,3-nonadjacent stereocenters leading to chiral pyrroloindolines.
Xin Li et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(48), 14290-14294 (2010-12-01)
A G Craan et al.
Toxicology, 56(1), 47-61 (1989-05-31)
The nephrotoxicity of glutathione (GSH) pathway metabolites derived from toluene (TOL), styrene (STYR), bromobenzene (BB), acrylonitrile (ACLN) and 2-chloroacrylonitrile (CACLN) were compared with that of dichlorovinylcysteine (DCVC), using renal brush border and basal-lateral uptake parameters as indices. Cysteine conjugates and
Yi Wang et al.
Journal of the American Chemical Society, 128(12), 3928-3930 (2006-03-23)
Catalytic tandem asymmetric reactions constitute a powerful strategy for the asymmetric construction of nonadjacent stereocenters in acyclic molecules directly from achiral precursors. In this Communication, we report a highly enantioselective and diastereoselective addition of trisubstituted carbon donors to 2-chloroacrylonitrile catalyzed
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