TMCE

CAS 26189-59-3, Cat. No EN300-367467
Reagent for chlorination and cyclization

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1-Chloro-N,N,2-trimethylpropenylamine (TMCE) is a powerful α-chloroenamine reagent that enables mild, neutral, and highly chemoselective chlorination of a broad range of substrates¹. It cleanly converts primary, secondary, benzylic, allylic, and propargylic alcohols into the corresponding chlorides with high yields and complete inversion of configuration, while leaving acid- and oxidation-sensitive groups intact. TMCE also transforms carboxylic acids into acid chlorides at low temperatures without racemization, and activates acids for coupling with organometallic reagents to give ketones. The keteniminium chloride generated in situ engages electron-rich partners in [2+2] cycloadditions to form β-lactams and reacts with azides, cyanides, phosphites, and metal carbonyl anions to give diverse products. Despite this broad reactivity, TMCE is shelf-stable when kept dry under nitrogen.

Synonyms: 1-сhloro-N,N,2-trimethylpropenylamine; (1-chloro-2-methylprop-1-en-1-yl)dimethylamine; TMCE