Sodium trifluoroacetate

Sodium trifluoroacetate
Names
	IUPAC name Sodium trifluoroacetate
	Other names Sodium perfluoroacetate ; Sodium 2,2,2-trifluoroacetate
Identifiers
CAS Number	2923-18-4;
3D model (JSmol)	Interactive image;
ChemSpider	68703;
ECHA InfoCard	100.018.982
EC Number	220-879-6;
PubChem CID	517019;
UNII	255JUV5YVI;
CompTox Dashboard (EPA)	DTXSID0062715 ;
	InChI Key: UYCAUPASBSROMS-UHFFFAOYSA-M; InChI=1S/C2HF3O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1;
	SMILES C(C(=O)[O-])(F)(F)F.[Na+];
Properties
Chemical formula	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
Solubility in water	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:
Pictograms
Signal word	Danger
Hazard statements	H300, H315, H319, H335, H410
Precautionary statements	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)	2 0 1
Flash point	Non-flammable
Autoignition; temperature	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). Infobox references

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]

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:

{\ce {CF3CO2- + HCl -> CF3CO2H + Cl-}}

{\ce {CF3CO2- + H2SO4 -> CF3CO2H + HSO4-}}

In general, trifluoroacetate reacts in equilibrium with hydronium cations to form trifluoroacetic acid:

{\ce {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 (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.

References

^ 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.
^ Prakash, G. K. Surya; Mathew, Thomas (2010), "Sodium Trifluoroacetate", Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289x.rn01136, ISBN 9780470842898

[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

[1]

[2]

Basicity

Preparation

Uses

See also

References