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Merck
CN

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

Key Documents

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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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR0801
MKBN6229V
BCBF8760V
MKBH5728
BCBF8760

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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)
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
E Eder et al.
Mutation research, 322(4), 321-328 (1994-10-01)
2-Chloroacrolein and 2-bromoacrolein are very potent direct mutagens not requiring metabolic activation in Salmonella typhimurium strains TA 100 and TA 1535. Mutagenic activities decrease with increasing degree of methyl substitution at carbon atom C-3 of the acrolein moiety from 2-chloroacrolein
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