Sodium trichloroacetate is a chemical compound with a formula of CCl3CO2Na. It is a colorless, water-soluble solid.
Preparation Sodium trichloroacetate is made by the neutralization of trichloroacetic acid with sodium hydroxide:
CCl3CO2H + NaOH → CCl3CO2Na + H2O
Reactions 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 with suitably strong acids:
CCl3CO−2 + H2SO4 → CCl3CO2H + HSO−4 Heating induces decarboxylation and hydrolysis, yielding chloroform and sodium bicarbonate: CCl3CO2Na + H2O → HCCl3 + NaHCO3 Under anhydrous conditions, thermal decarboxylation produces the trichloromethyl anion, which is a sufficiently nucleophilic to add to carbonyl functional groups in aldehydes, carboxylic acid anhydrides, ketones, and acyl halides. It is thus a precursor for the Jocic–Reeve reaction.
Applications Sodium trichloroacetate is a commercial herbicide. It is also used in the dye industry. In the laboratory, it is used to increase sensitivity and precision during transcript mapping.
Safety Its use as a herbicide is regulated. The compound has a halflife of week in soils. It is of modest toxicity, with an LD50 (oral, rats) of grams/kg.
See also Sodium chloroacetate
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