CAS 598-99-2, Cat. No EN300-7592175
Reagent the precursor of dichlorocarbene
Methyl trichloroacetate is a versatile reagent primarily used as a precursor for dichlorocarbene generation1. The reagent reacts with alkali metal alkoxides (e.g., MeONa) to produce dichlorocarbene, which can undergo cycloaddition with alkenes, forming gem-dichlorocyclopropanes in high yields. It operates efficiently under mild reaction conditions (between -40 °C and room temperature) and exhibits higher yields compared to alternative methods of carbene formation. Depending on conditions of reaction with carbonyl, either to α-chloroglycidic esters or to α-chloro-α,β-unsaturated esters can be produced2.
Synonyms: acetic acid, trichloro-, methyl ester (6CI, 7CI, 8CI, 9CI); methyl α,α,α-trichloroacetate; trichloroacetic acid methyl ester; methyl trichloroacetate
Selected publications
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Ethyl Trichloroacetate.
Dormoy J.; Castro B. Encyclopedia of Reagents for Organic Synthesis 2001. DOI: 10.1002/047084289X.re117
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Fe(0)-Mediated Synthesis of Tri- and Tetra-Substituted Olefins from Carbonyls: An Environmentally Friendly Alternative to Cr(II).
Falck J.; Bejot R.; Barma D.; Bandyopadhyay A.; Joseph S.; Mioskowski C. J Org Chem 2006, 71 (21), 8178–8182. DOI: 10.1021/jo061445u