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.
Preparationedit
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]
^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, ISBN9780470842898
April 14, 2024
sodium, trifluoroacetate, chemical, compound, with, formula, cf3co2na, sodium, salt, trifluoroacetic, acid, used, source, trifluoromethylations, namesiupac, name, other, names, sodium, perfluoroacetate, sodium, trifluoroacetateidentifierscas, number, 2923, mod. 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 NamesIUPAC name Sodium trifluoroacetateOther names Sodium perfluoroacetate Sodium 2 2 2 trifluoroacetateIdentifiersCAS Number 2923 18 43D model JSmol Interactive imageChemSpider 68703ECHA InfoCard 100 018 982EC Number 220 879 6PubChem CID 517019UNII 255JUV5YVICompTox Dashboard EPA DTXSID0062715InChI Key UYCAUPASBSROMS UHFFFAOYSA MInChI 1S C2HF3O2 Na c3 2 4 5 1 6 7 h H 6 7 q 1 p 1SMILES C C O O F F F Na PropertiesChemical formula C 2F 3Na O 2Molar mass 136 005 g mol 1Appearance White crystalline powderDensity 1 49 g mL 1Melting point 207 C 405 F 480 K Boiling point DecomposesSolubility in water 625 g LSolubility soluble in alcohol acetonitrile dimethylformamide and most of polar organic solventsAcidity pKa 0 23 conjugate acid HazardsOccupational safety and health OHS OSH Main hazards Toxic Irritant Harmful to environmentGHS labelling PictogramsSignal word DangerHazard statements H300 H315 H319 H335 H410Precautionary 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 P501NFPA 704 fire diamond 201Flash point Non flammableAutoignitiontemperature Non flammableRelated compoundsOther anions Sodium trichloroacetateOther cations Lithium trifluoroacetatePotassium trifluoroacetateRelated compounds Sodium formateExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Basicity 2 Preparation 3 Uses 4 See also 5 ReferencesBasicity editWith 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 CF3CO2 HCl CF3CO2H Cl displaystyle ce CF3CO2 HCl gt CF3CO2H Cl nbsp CF3CO2 H2SO4 CF3CO2H HSO4 displaystyle ce CF3CO2 H2SO4 gt CF3CO2H HSO4 nbsp In general trifluoroacetate reacts in equilibrium with hydronium cations to form trifluoroacetic acid CF3CO2 H3O CF3CO2H H2O displaystyle ce CF3CO2 H3O lt gt gt CF3CO2H H2O nbsp The general reaction with hydronium is in equilibrium due to the similarity in pKa between trifluoroacetic acid and the hydronium ion Preparation editOne 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 editSodium trifluoroacetate is a useful reagent for trifluoromethylation nbsp The trifluoromethylation process with sodium trifluoroacetate See also editSodium fluoroacetate Trifluoroacetic acid Sodium acetateReferences edit 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 Retrieved from https en wikipedia org w index php title Sodium trifluoroacetate amp oldid 1198598323, wikipedia, wiki, book, books, library,
