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407-25-0 - Trifluoroacetic anhydride, 99+% - TFAA - A13614 - Alfa Aesar

A13614 Trifluoroacetic anhydride, 99+%

CAS Number
407-25-0
Synonyms
TFAA

Size Price ($) Quantity Availability
25g 19.98
100g 48.41
500g 149.35
2500g 564.25
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Trifluoroacetic anhydride, 99+%

MDL
MFCD00000416
EINECS
206-982-9

Chemical Properties

Formula
C4F6O3
Formula Weight
210.03
Melting point
-65°
Boiling Point
39-40°
Density
1.503
Refractive Index
1.2690
Sensitivity
Moisture Sensitive
Solubility
Miscible with benzene, dichloromethane, diethyl ether, dimethylformamide, terahydrofuran and acetonitrile.

Applications

Trifluoroacetic anhydride is used for the introduction of trifluoroacetyl group in organic synthesis. It is involved in the preparation of N- and O-trifluoroacetyl derivatives of a wide range of biologically active compounds for gas chromatography analysis. It plays an important role as desiccant for trifluoroacetic acid. It is also used in the oxidation of aldehydes to acids, esters, amides as well as in the protection of alcohols and amines. In addition, it is used as analytical reagents, solvents and dehydration condensing agent. It serves as an intermediate of fluorine fine chemicals, pharmaceuticals and agrochemicals.

Notes

Hygroscopic and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents, strong bases, strong acids, and alcohols.

Literature References

Trifluoroacetylating agent for protection of alcohols and amines: Helv. Chim. Acta., 37, 443 (1954); Tetrahedron, 43, 5583 (1987); Tetrahedron Lett., 28, 4737 (1987), useful, e.g. as volatile derivatives in GC: J. Chromat., 43, 129 (1969); 61, 225 (1971); 93, 223, 447 (1974); D. R. Knapp, Handbook of Analytical Derivatisation Reactions, Wiley, N.Y. (1979); Handbook of Derivatives for Chromatography, 2nd ed., K. Blau and J. M. Halket, Eds., Wiley, Chichester (1993).

Trifluoroacetyl esters are rapidly hydrolyzed at pH 7: Tetrahedron Lett., 1039 (1963). Trifluoroacetamides are also readily hydrolyzed e.g. by mild base; selective cleavage of a trifluoroacetamide can be achieved in the presence of a methyl ester: J. Org. Chem., 54, 2498 (1989). For the racemization-free removal of the N-trifluoroacetyl group from peptides by NaBH4, see: Chem. Ber., 103, 2437 (1970).

In pyridine and dichloromethane or ether, converts acid chlorides to trifluoromethyl ketones in good yields via a trifluoroacyl ketene intermediate: Tetrahedron, 51, 2573 (1995). The method has been extended to the synthesis of a range of trifluoromethylated heterocycles: Tetrahedron, 51, 2585 (1995):

Mild conversion of aryl halides to aryl trifluoromethyl ketones via Pd catalyzed stannylation: Synlett, 165 (1995).

In pyridine, dehydrates carboxamides or aldoximes to nitriles: Tetrahedron Lett., 1813 (1977); Synthesis, 56, (1979). With triethylamine, effects the dehydration of aldols to enones, where other methods are less successful: Org. Synth. Coll., 8, 210 (1993).

For the ɑ-trifluoroacetylation of a phosphonium salt in a route to perfluoroalkyl acetylenes, see: Org. Synth. Coll., 9, 436 (1998). For reaction scheme, see (Ethoxycarbonyl­methyl)­triphenyl­phosphonium bromide, A16347.

Alternative to Oxalyl­ chloride, A18012, for activation of Dimethyl­ sulfoxide, A13280 in the low temperature Swern oxidation of alcohols to aldehydes or ketones: J. Org. Chem., 41, 957 (1976); Tetrahedron, 34, 1651 (1978). This reagent often gives cleaner reactions and improved yields, e.g. in the synthesis of a sensitive 1,2-dione from the diol: J. Org. Chem., 52, 4851 (1987).

Jones, D. H.; Smith, K.; Elliott, M. C.; El-Hiti, G. A. Factors affecting reactions of trialkylcyanoborates with imidoyl chlorides/trifluoroacetic anhydride. Tetrahedron 2015, 71 (36), 6285-6289.

Shibakami, M.; Tsubouchi, G.; Sohma, M.; Hayashi, M. One-pot synthesis of thermoplastic mixed paramylon esters using trifluoroacetic anhydride. Carbohydr. Polym. 2015, 119, 1-7.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H332-H402-H412

Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if inhaled. Harmful to aquatic life. Harmful to aquatic life with long lasting effects.

Precautionary Statements: P260-P261-P273-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
746197
Hazard Class
8
Packing Group
I
Harmonized Tariff Code
2915.90
TSCA
Yes
RTECS
AJ9800000

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