Gourt Home::Gourt :: Trifluoroacetic acid
| Trifluoroacetic acid | |
|---|---|
| General | |
| Systematic name | trifluoroethanoic acid |
| Other names | perfluoroacetic acid trifluoracetic acid TFA |
| Molecular formula | C2HF3O2 |
| SMILES | FC(F)(F)C(O)=O |
| Molar mass | 114.03 g/mol |
| Appearance | colorless liquid |
| CAS number | * |
| Properties | |
| Density and phase | 1.5351 g/cm3, 20 °C |
| Solubility in water | miscible |
| Melting point | -15.4 °C; 257.75 K |
| Boiling point | 72.4 °C; 345.55 K |
| Acidity (pKa) | 0.3 |
| Viscosity | ? cP at ? °C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | corrosive |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: S: |
| RTECS number | ? |
| Related compounds | |
| Related compounds | acetic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Chemical infobox | |
Trifluoroacetic acid (TFA) is a strong, hygroscopic, non-oxidizing, organic acid with a molecular formula C2HF3O2. The molecular structure is similar to acetic acid, with substitution of three fluorine atoms on the methyl group. The electronic-withdrawing nature of the fluorine atoms stabilizes the dissociated anion, leading to stronger acidity compared to acetic acid. TFA is a reagent used frequently in organic synthesis due to its nature as an organic-soluble strong acid. It is also frequently used as a buffer in liquid chromatography for separation of organic compounds, particularly peptides and small proteins.
Synthesis
Electrofluorination of acetic acid with the Simons method is the best way to obtain trifluoroacetic acid. The anodic reaction of the electrolysis of a mixture of hydrogen fluoride and acetic acid below the voltage at which elemental fluorine (F2) develops is a mild reaction which leaves the carboxylic group intact.
External links
"Trifluoroacetic acid"
