Sodium trifluoroacetate

Sodium trifluoroacetate is a chemical compound with a formula of CF₃CO₂Na. It is the sodium salt of trifluoroacetic acid. It is used as a reagent in synthetic organic chemistry .

Basicity

With a pK_a of 0.23 for trifluoroacetic acid, the trifluoroacetate ion is an extremely weak base compared to acetic acid, which has a pK_a of 4.76. This is due to the electron-withdrawing effect of the three fluorine atoms adjacent the carboxylate group. Strong acids such as hydrochloric acid or sulfuric acid can protonate the trifluoroacetate ion to trifluoroacetic acid:
In general, trifluoroacetate reacts in equilibrium with hydronium cations to form trifluoroacetic acid:
The general reaction with hydronium is in equilibrium due to the similarity in pK_a between trifluoroacetic acid and the hydronium ion.

One convenient method is by dissolving an equivalent amount of sodium carbonate in a 50% aqueous solution of trifluoroacetic acid. The solution is filtered and evaporated by vacuum evaporation. The solid obtained is dried under vacuum at 100 °C.

Sodium trifluoroacetate is a useful reagent for trifluoromethylation.