Sodium trichloroacetate

Sodium trichloroacetate is a chemical compound with a formula of CCl₃CO₂Na. It is used to increase sensitivity and precision during transcript mapping. It was previously used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.

Preparation

Sodium trichloroacetate is made by the neutralization of trichloroacetic acid with sodium hydroxide:

Reactions

Basicity

Sodium trichloroacetate is a weaker base than sodium acetate because of the electron-withdrawing nature of the trichloromethyl group. Sodium trifluoroacetate is likewise an even weaker base. Sodium trichloroacetate can easily be protonated in the presence of suitably strong acids:

Trichloromethyl-anion precursor

This reagent is useful for introducing the trichloromethyl group into other molecules. Decarboxylation produces the trichloromethyl anion, which is a sufficiently strong nucleophile to attack various carbonyl functional groups, such as aldehydes, carboxylic acid anhydrides, ketones, and acyl halides.