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76-05-1 - Trifluoroacetic acid, 99% - TFA - L06374 - Alfa Aesar

L06374 Trifluoroacetic acid, 99%

CAS-Nummer
76-05-1
Synonyme
TFA

Größe Preis ($) Menge Verfügbarkeit
25ml 29,70
100ml 50,50
500ml 147,00
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Trifluoroacetic acid, 99%

MDL
MFCD00004169
EINECS
200-929-3

Chemische Eigenschaften

Formel
C2HF3O2
Molmasse
114.02
Schmelzpunkt
-15°
Siedepunkt
72-73°
Dichte
1.480
Brechungsindex
1.2840
Sensitivität
Hygroscopic
Löslichkeit
Miscible with ether, acetone, ethanol, benzene, hexane and carbon tetrachloride.

Anwendungen

The combination of properties like solubility in most of the solvents, volatility, catalytic property, and strong acidity with non-oxidizing nature makes it a widely used reagent in organic synthesis. Trifluoroacetic acid is an important building block in the synthesis of pharmaceuticals, agrochemicals and performance products. It is a precursor to many fluorinated compounds, and widely used in peptide synthesis and other organic transformations involving deprotection of t-BOC group. TFA finds use as an ion pairing agent in liquid chromatography, as a solvent in NMR spectroscopy and as a calibrant in mass spectrometry.

Bemerkungen

Trifluoroacetic acid (TFA) is a stable, hygroscopic, volatile and low-boiling organic acid. Storage in a cool place is recommended.

Literaturverweise

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).

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).

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.

López, S. E.; Salazar, J. Trifluoroacetic acid: Uses and recent applications in organic synthesis. J. Fluorine Chem. 2013, 156, 73-100.

Natu, A. D.; Burde, A. S.; Limaye, R. A.; Paradkar, M. V. Acceleration of the Dakin reaction by trifluoroacetic acid. J. Chem. Res. 2014, 38 (6), 325-386.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H332-H314

Harmful if inhaled. Causes severe skin burns and eye damage.

Sicherheitshinweise: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,9681
Beilstein
742035
Gefahrenklasse
8
Verpackungsgruppe
I
Harmonized Tariff Code
2915.90
TSCA
Yes
RTECS
AJ9625000

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