Wikipedia

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 Edit this at Wikidata
EC Number
  • 220-879-6
UNII
  • Key: UYCAUPASBSROMS-UHFFFAOYSA-M
  • InChI=1S/C2HF3O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1
  • C(C(=O)[O-])(F)(F)F.[Na+]
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
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, Irritant, Harmful to environment
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H300, H315, H319, H335, H410
P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
0
1
Flash point Non-flammable
Non-flammable
Related compounds
Other anions
 Sodium trichloroacetate
Other cations
 Lithium trifluoroacetate
Potassium trifluoroacetate
Related compounds
 Sodium formate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Basicity

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With a pKa of 0.23 for trifluoroacetic acid, the trifluoroacetate ion is an extremely weak base compared to acetic acid, which has a pKa 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 pKa between trifluoroacetic acid and the hydronium ion.

Preparation

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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

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Sodium trifluoroacetate is a useful reagent for trifluoromethylation.

 
The trifluoromethylation process with sodium trifluoroacetate.

See also

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References

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