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C19651

Sigma-Aldrich

Chloroacetonitrile

99%

Synonym(s):

α-Chloroacetonitrile, 2-Chloroacetonitrile, Chloromethyl cyanide, Cyanomethyl chloride, Monochloroacetonitrile

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About This Item

Linear Formula:
ClCH2CN
CAS Number:
107-14-2
Molecular Weight:
75.50
Beilstein:
506028
EC Number:
203-467-0
MDL number:
MFCD00001885
UNSPSC Code:
12352100
PubChem Substance ID:
24892453
NACRES:
NA.22

vapor density

3 (vs air)

vapor pressure

1.78 psi ( 20 °C)

Assay

99%

form

liquid

refractive index

n20/D 1.422 (lit.)

bp

124-126 °C (lit.)

density

1.193 g/mL at 25 °C (lit.)

SMILES string

ClCC#N

InChI

1S/C2H2ClN/c3-1-2-4/h1H2

InChI key

RENMDAKOXSCIGH-UHFFFAOYSA-N

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Application

Chloroacetonitrile can be used:
  • For the synthesis of ionic liquids containing nitrile functionalized imidazolium salts.
  • For the synthesis of cyanomethyl dodecyl trithiocarbonate, a reversible addition-fragmentation chain transfer (RAFT) agent.
  • As an alkylating reagent for the synthesis of derivatives of triazolyl thiazoles to be used as anti-tuberculosis agents.
  • As a reagent in photo Meerwein addition reaction for amino-arylation of alkenes.
  • As an esterifying agent in the synthesis of a cytotoxic natural product: apicularen A.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

129.2 °F

Flash Point(C)

54 °C

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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Synthesis and characterization of ionic liquids incorporating the nitrile functionality.
Zhao D, et al.
Inorganic Chemistry, 43(6), 2197-2205 (2004)
Synthesis of new S-derivatives of clubbed triazolyl thiazole as anti-Mycobacterium tuberculosis agents.
Shiradkar MR, et al.
Bioorganic & Medicinal Chemistry, 15(12), 3997-4008 (2007)
Thiocarbonylthio end group removal from RAFT-synthesized polymers by radical-induced reduction.
Chong YK, et al.
Macromolecules, 40(13), 4446-4455 (2007)
Total synthesis of (-)-apicularen A.
Su Q and Panek JS
Journal of the American Chemical Society, 126(8), 2425-2430 (2004)
The photoredox-catalyzed Meerwein addition reaction: intermolecular amino-arylation of alkenes.
Prasad Hari D, et al.
Angewandte Chemie (International Edition in English), 53(3), 725-728 (2014)
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