Trifluoroacetic acid

• Catalog No.: L06374
• CAS Number: 76-05-1
• M. F.: C2HF3O2
• M. W.: 114.0233496
• Purity: 99%

SYNONYMS

• Title: 三氟乙酸
• IUPAC name: trifluoroacetic acid
• IUPAC Traditional name: trifluoroacetic acid
• Synonyms: TFA

DATABASE IDS

• MDL Number: MFCD00004169
• EC Number: 200-929-3
• Merck Index: 149681
• Beilstein Number: 742035
• CAS Number: 76-05-1

PROPERTIES

• Purity: 99%
• Boiling Point: 72-73°C
• Density: 1.480
• Melting Point: -15°C
• Refractive Index: 1.2840
• GHS Hazard statements: H314-H332-H412
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 20-35-52/53
• RTECS: AJ9625000
• Safety Statements: 9-26-27/28-45-61
• Storage Warning: Hygroscopic
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2699
• Packing Group: I

REFERENCES

• Carrying out the Curtius rearrangement of acyl azides in TFA leads directly to the trifluoroacetamide, which can be readily hydrolyzed to the free amine: Synthesis, 38 (1983).
• Strong organic acid, widely used in peptide synthesis to cleave N-Boc and t-butyl ester groups: Helv. Chim. Acta, 46, 870 (1963); see also Org. Synth. Coll., 9, 24, 268 (1998). For peptide reagents, see Appendix 6. For selective cleavage of Boc in the presence of Cbz (Z), using 70% TFA in water, see: Liebigs Ann. Chem., 749, 90 (1971). For selective cleavage of benzyl, benzhydryl and trityl ethers in the presence of ester functions, see: Synthesis, 249 (1983).
• Also catalyzes the cleavage of t-butyl groups from t-butylphenols, by reverse Friedel-Crafts reaction: Tetrahedron, 29, 4003 (1973). Similarly, hindered aryl ketones or aromatic carboxylic acids undergo deacylation: Synthesis, 979 (1985).
• With sodium nitrite, has been used for the cleavage of tosylhydrazones: Synthesis, 207 (1979); for nitrosation of anisole and derivatives, avoiding possible loss of the alkyl group: Acta Chem. Scand., 44, 152 (1990); for diazotization of weakly basic arylamines such as pentafluoroaniline or 3,5-dinitroaniline: Synthesis, 566 (1988); and in the presence of formamide, for deamination of arylamines: J. Chem. Soc., Perkin 1, 873 (1986).
• For use of TFA as a catalyst in the Meerwein-Ponndorf-Verley reduction, see Aluminum isopropoxide, 14007. For use in the modification of the reducing properties of borohydride, see Sodium borohydride, 13432. For use in the ionic hydrogenation, see Triethylsilane, A10320.