Chloroacetonitrile, 98+%

General References:

1. Forms cyanomethyl esters with carboxylic acids, e.g. in the presence of Et₃N, which are a useful protection method; the esters are readily cleaved by Na₂S in aqueous acetone: Synth. Commun., 22, 693 (1992).
2. Good yields of ß-hydroxy nitriles have been obtained by Reformatsky-type reaction with aldehydes and ketones using Zn and TMS chloride: Tetrahedron Lett., 31, 2205 (1990). See Bromoacetonitrile, A13933.
3. In the presence of base, Darzens condensation with aldehydes and ketones, under conventional or phase-transfer conditions, gives glycidonitriles (cyano epoxides), readily converted to the homologated carboxylic acids, esters or aldehydes with loss of cyanide: J. Chem. Soc., Chem. Commun., 988 (1974); Coll. Czech. Chem. Commun., 53, 822 (1988).
4. Ritter reaction with tertiary alcohols yields 2-chloroacetamides which, on treatment with thiourea, provides a high-yield conversion of tertiary alcohols to the corresponding amines: Synthesis, 1709 (2000):
5. For use in vicarious nucleophilic substitution of hydrogen in nitro-substituted hetereocycles, see 2-Nitrothiophene, A17464.
6. Hoseini, S. J.; Nasrabadi, H.; Fath, R. H.; Moradi, Z.; Rashidi, M. Oxidative Addition of Propargyl Halides, Chloroacetonitrile, and Ethyl Chloroacetate to a Dimethylplatinum(II) Complex: Kinetic and DFT Studies. Organometallics 2014, 33 (7), 1689-1699.
7. Kimura, S. Y.; Komaki, Y.; Plewa, M. J.; Marinas, B. J. Chloroacetonitrile and N,2-Dichloroacetamide Formation from the Reaction of Chloroacetaldehyde and Monochloramine in Water. Environ. Sci. Technol. 2013, 47 (21), 12382-12390.