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| Trifluoroacetic acid | |
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| IUPAC name | 1,1,1-Trifluoroethanoic acid |
| Other names | Perfluoroacetic acid Trifluoroethanoic acid TFA |
| Identifiers | |
| CAS number | 76-05-1 |
| RTECS number | AJ9625000 |
| SMILES |
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| ChemSpider ID | |
| Properties | |
| Molecular formula | C2HF3O2 |
| Molar mass | 114.02 g/mol |
| Appearance | colorless liquid |
| Density | 1.5351 g/cm3, 20 °C |
| Melting point |
-15.4 °C; 257.75 K |
| Boiling point |
72.4 °C; 345.55 K |
| Solubility in water | miscible |
| Acidity (pKa) | 0.3 |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Highly corrosive |
| NFPA 704 |
 1
3
1
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| R-phrases | R20 R35 R52/53 |
| S-phrases | S9 S26 S27 S28 S45 S61 |
| Flash point | -3 °C |
| Related compounds | |
| Related compounds | Acetic acid Trichloroacetic acid Perfluorononanoic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Trifluoroacetic acid (TFA) is the chemical compound with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the three very electronegative fluorine atoms. Relative to acetic acid, TFA is almost 100,000-fold more acidic. TFA is widely used in organic chemistry.
Uses
TFA is a reagent used frequently in organic synthesis because of a combination of convenient properties: volatility, solubility in organic solvents, and its strength.1 It is also less oxidizing than sulfuric acid but more readily available in anhydrous form than hydrochloric acid. One complication to its use is that TFA forms an azeotrope with water with a boiling point of 105 °C.
It is also used as a ion pairing agent in liquid chromatography for separation of organic compounds, particularly peptides and small proteins. It is a versatile solvent for NMR spectroscopy (for materials stable in acid).
The derived acid anhydride, trifluoroacetic anhydride (TFAA), [CF3C(O)]2O, is a common reagent for introducing the trifluoracetyl group.
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.
References
- ^ Eidman, K. F.; Nichols, P. J. "Trifluoroacetic Acid" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289
Wikipedia content modification information:
- This page was last modified on 25 November 2008, at 05:50.
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