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Chloroacetonitrile is used in the electrochemical synthesis of cyanoacetic acid with carbon dioxide. It is involved in phase-transfer-catalyzed Darzen's condensation reaction with cyclohexanone. It is also used as an eluent additive in thermospray liquid chromatography/mass spectrometry. Further, it is used to prepare polysubstituted pyrido[1,2-a]benzimidazole by reacting with other reactant such as malononitrile, aromatic aldehyde and pyridine.
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).
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.
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).
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):
For use in vicarious nucleophilic substitution of hydrogen in nitro-substituted hetereocycles, see 2-Nitrothiophene, A17464.
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.
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.
Hazard Statements: H226-H301+H331-H310-H319
Flammable liquid and vapour. Toxic if swallowed. Toxic if inhaled. Fatal in contact with skin. Causes serious eye irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P262-P264b-P270-P271-P280-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P310-P311-P330-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician. Rinse mouth. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant