[A13614] CAS 407-25-0 | Trifluoroacetic anhydride, 99+%

CAS : 407-25-0
UN# : UN3265
MDL : MFCD00000416
Hazard Class : 8
EINECS : 206-982-9
Packing Group : I

Other name :

TFAA

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. Store under Nitrogen.
Form : Liquid
Solubility : Miscible with benzene, dichloromethane, diethyl ether, dimethylformamide, terahydrofuran and acetonitrile.

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).

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.Other References:Beilstein: 746197UN#: UN3265

Grade Specifications

Grade Specifications

Hazard Statements : H314-H318Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501aDo not breathe dust/fume/gas/mist/vapours/spray.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.