Sodium trifluoroacetate is a chemical compound with a formula of CF₃CO₂Na. It is the

sodium salt Sodium salts are salts composed of a sodium cation and the conjugate base anion of some inorganic or organic acids. They can be formed by the neutralization of such acids with sodium hydroxide. Categorization Sodium salts can be categorized i ...

trifluoroacetic acid Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with ...

. It is used as a source of

trifluoromethylation Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notab ...

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 In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,...; ''carboxyla ...

. Strong acids such as

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid. It is a component of the gastric acid in the dig ...

or sulfuric acid can protonate the trifluoroacetate ion to

: :CF3CO2- + HCl -> CF3CO2H + Cl- :CF3CO2- + H2SO4 -> CF3CO2H + HSO4- In general, trifluoroacetate reacts in equilibrium with hydronium cations to form trifluoroacetic acid: :CF3CO2- + H3O+ <=>> CF3CO2H + H2O The general reaction with hydronium is in equilibrium due to the similarity in pK_a between trifluoroacetic acid and the hydronium ion.

Preparation

One convenient method is by dissolving an equivalent amount of sodium carbonate in 50% aqueous solution of trifluoroacetic acid. The solution is filtered and evaporated by

vacuum evaporation Vacuum evaporation is the process of causing the pressure in a liquid-filled container to be reduced below the vapor pressure of the liquid, causing the liquid to evaporate at a lower temperature than normal. Although the process can be applied to ...

(with special care to avoid decomposition of the salt by overheating). The solid obtained is dried under vacuum at 100 °C.

Uses

Sodium trifluoroacetate is a useful reagent for

. :

Trifluoromethylation with sodium trifluoroacetate

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References

Organic sodium salts Trifluoroacetates

Basicity

Preparation

Uses

See also

References