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 source of trifluoromethylations.[1]

Sodium trifluoroacetate
Names
IUPAC name
Sodium trifluoroacetate
Other names
Sodium perfluoroacetate
Sodium 2,2,2-trifluoroacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.982
EC Number
  • 220-879-6
UNII
Properties
C2F3NaO2
Molar mass 136.005 g·mol−1
Appearance White crystalline powder
Density 1.49 g mL−1
Melting point 207 °C (405 °F; 480 K)
Boiling point Decomposes
625 g/L
Solubility soluble in alcohol, acetonitrile, dimethylformamide and most of polar organic solvents
Acidity (pKa) 0.23 (conjugate acid)
Hazards
Main hazards Toxic, Irritant, Harmful to environment
GHS pictograms
GHS Signal word Danger
H300, H315, H319, H335, H400, H410
P261, P264, P270, P271, P273, P280, P301+310, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P391, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
0
2
1
Flash point Non-flammable
Non-flammable
Related compounds
Other anions
 Sodium trichloroacetate
Related compounds
 Sodium formate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Basicity

With the pKa of 0.23 for trifluoroacetic acid (compared to acetic acid, which has a pKa of 4.76), the trifluoroacetate ion is clearly a much weaker base. This is because of the electron-withdrawing effect on the 3 fluorine atoms adjacent to the carbon atom. With strong acids, such as hydrochloric acid or sulfuric acid, the trifluoroacetate ion can be protonated:

It also partially reacts with hydronium cations to form the acid:

The equilibrium is not complete because of the smaller pKa difference of the acid and hydronium.

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 (with special care to avoid decomposition of the salt by overheating). The solid obtained is dried under vacuum at 100 °C.[2]

Uses

Sodium trifluoroacetate is a useful reagent for trifluoromethylation.

The trifluoromethylation process with sodium trifluoroacetate.

See also

References
  1. "Trifluoromethylation of carbonyl compounds with sodium trifluoroacetate". Journal of Fluorine Chemistry. 126 (6): 937–940. June 2005. doi:10.1016/j.jfluchem.2005.04.012.
  2. Prakash, G. K. Surya; Mathew, Thomas (2010), "Sodium Trifluoroacetate", Encyclopedia of Reagents for Organic Synthesis, American Cancer Society, doi:10.1002/047084289x.rn01136, ISBN 9780470842898
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