Benzyltriethylammonium chloride is used as a catalyst in the preparation of 2-phenylbutyronitrile from phenyl acetonitrile. It is involved in the Knoevenagel condensation of carbonyl compounds with active methylene compounds to give olefinic products. It acts as a phase transfer catalyst used in the alkylation reaction. It reacts with 1H-Pyridine-2-thione to get 2-Benzylsulfanyl-pyridine.
Phase-transfer catalyst (see Appendix 2) which has found wide application in the generation of carbenes from haloforms and related precursors: Org. Synth. Coll., 7, 12 (1990); 8, 223 (1993). Dihalocarbenes have been used to convert primary amines (t-butylamine) to isonitriles: Org. Synth. Coll., 6, 232 (1988), and in the dehydration of amides, thioamides and oximes to nitriles: Tetrahedron Lett., 2121 (1973). Ureas give cyanamides.
For use in the formation of polysubstituted cyclopropanes by carbene-type addition to double bonds, see Ethyl chloroacetate, A15554.
For use in the dialkylation of malonate esters to give cyclopropane derivatives, see: Synthesis, 54 (1985); Org. Synth. Coll., 7, 411 (1993).
In combination with NaBr in acetonitrile, has been used for the mono-dealkylation of phosphonate diesters: Synthesis, 453 (1983).
Ramos, M. D.; Gomez, G. I. G.; Gonzalez, N. S. Immobilization of Candida rugosa lipase on bentonite modified with benzyltriethylammonium chloride. J. Mol. Catal. B: Enzym. 2014, 99, 79-84.
Wu, Y. C.; Leowanawat, P.; Sun, H. J.; Partridge, B. E.; Peterca, M.; Graf, R.; Spiess, H. W.; Zeng, X.; Ungar, G.; Hsu, C. S.; Heiney, P. A.; Percec, V. Complex Columnar Hexagonal Polymorphism in Supramolecular Assemblies of a Semifluorinated Electron-Accepting Naphthalene Bisimide. J. Am. Chem. Soc. 2015, 137 (2), 807-819.
Hazard Statements: H303-H315-H319-H335
May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.