trifluoroacetyl 2,2,2-trifluoroacetate

• ChemBase ID: 99501
• Molecular Formular: C4F6O3
• Molecular Mass: 210.0314192
• Monoisotopic Mass: 209.97516318
• SMILES: FC(F)(F)C(=O)OC(=O)C(F)(F)F
• Canonical SMILES: O=C(C(F)(F)F)OC(=O)C(F)(F)F
• InChI: InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10
• InChIKey: QAEDZJGFFMLHHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trifluoroacetyl 2,2,2-trifluoroacetate
• IUPAC Traditional name: trifluoroacetic anhydride
• Synonyms: Trifluoroacetic anhydride 99%; 2,2,2-Trifluoroacetic anhydride; TFAA; Trifluoroacetic anhydride; TRIFLUOROACETIC ANHYDRIDE; 三氟乙酸酐

Database IDs

• CAS Number: 407-25-0
• EC Number: 206-982-9
• MDL Number: MFCD00000416
• Beilstein Number: 746197
• PubChem SID: 162085766; 24889536; 24846727
• PubChem CID: 9845
• Wikipedia Title: Trifluoroacetic_anhydride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9521378
• LogD (pH = 7.4): 1.9521378
• Log P: 1.9521378
• Molar Refractivity: 24.1024 cm^3
• Polarizability: 9.386645 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: clear, colorless liquid
• Melting Point: -63°C; -65 °C(lit.); -65°C; -65°C
• Boiling Point: 39- 40°C; 39°C; 39.5-40 °C(lit.); 39-40°C; 39-40°C; 40°C
• Density: 1.487 g/ml; 1.487 g/mL; 1.498 g/ml; 1.503; 1.511; 1.511 g/mL at 20 °C(lit.)
• Refractive Index: 1.269; 1.2690; n20/D 1.3(lit.)
• Vapor Pressure: 6.28 psi ( 20 °C)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Corrosive/Harmful/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: AJ9800000
• European Hazard Symbols: Corrosive (C)
• UN Number: 1760; 3265; UN3265
• German water hazard class: 2
• Hazard Class: 8
• Packing Group: 1; I
• Australian Hazchem: 2X
• Risk Statements: 14-20-35-52/53; 35; R:14-34; R:35
• Safety Statements: 20-26-36/37/39-45-60; 26-36/37/39-43-45-61; S:26-27/28-36/37/39-46-64; S:27/28-30-36/37/39-45
• EU Classification: C9
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H318; H314-H332; H314-H332-H412
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P273-P280-P305 + P351 + P338-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 3265 8/PG 1
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ~99%; ≥99%; ≥99.0% (GC); 95+%; 97%; 99+%
• Grade: for GC derivatization; puriss. p.a.; purum; ReagentPlus®
• Derivatization reagent for: Acetylations; Acylations; Esterifications
• Linear Formula: (CF3CO)2O

DETAILS

MP Biomedicals - 02190285

Clear, colorless liquid
Purity: ~99%
1 ml = approx. 1.49 g

MP Biomedicals - 05219309

MP Biomedicals Rare Chemical collection

Apollo Scientific Ltd - PC7170

Useful trifluoroacetylating agent for the protectionof alcohols & amines: Helv.Chim.Acta., 37, 443 (1954)Ask for a bulk quote. Packaged in Safebreak bottles

Sigma Aldrich - 106232

Packaging
10×1 g in ampule
3 kg in glass bottle
25 kg in comp drum
25, 100, 500 g in glass bottle
Application
For the preparation of N- and O-trifluoroacetyl derivatives of a wide range of biologically active compounds for GC analysis. Also used in the oxidation of aldehydes to acids, esters, or amides.1
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 91719

Other Notes
For the protection of prim. and sec. amines; derivatives are more volatile1

Sigma Aldrich - 91720

Other Notes
Powerful activator in the DMSO oxidation of alcohols to carbonyl compounds1,2

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