Description

Trifluoroacetic anhydride (CAS 407-25-0) is a highly reactive and versatile fluorinated reagent with the molecular formula C₄F₆O₃. This colorless to pale yellow liquid is widely used in organic synthesis, particularly as a strong acylating and dehydrating agent. Its IUPAC name, (2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate, reflects its symmetrical anhydride structure derived from trifluoroacetic acid. With a boiling point of 39-40°C and a density of 1.511 g/mL at 25°C, it is moisture-sensitive and should be stored under inert conditions. Ideal for peptide coupling, esterification, and introducing trifluoroacetyl groups, this compound is a staple in pharmaceutical, agrochemical, and materials science research. Available in high-purity grades (≥99%), it is packaged in amber glass bottles to ensure stability.

Properties

• CAS Number: 407-25-0
• Complexity: 201
• IUPAC Name: (2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate
• InChI: InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10
• InChI Key: QAEDZJGFFMLHHQ-UHFFFAOYSA-N
• Exact Mass: 209.97516283
• Molecular Formula: C4F6O3
• Molecular Weight: 210.03
• SMILES: C(=O)(C(F)(F)F)OC(=O)C(F)(F)F
• Topological: 43.4
• Monoisotopic Mass: 209.97516283
• Physical Description: Liquid
• Vapor Pressure: 41.2 [mmHg]
• Synonyms: TRIFLUOROACETIC ANHYDRIDE, 407-25-0, Trifluoroacetic acid anhydride, Bis(trifluoroacetic) anhydride, Acetic acid, trifluoro-, anhydride, Perfluoroacetic anhydride, Trifluoroacetyl anhydride, Hexafluoroacetic anhydride, Anhydrid kyseliny trifluoroctove, 5ENA87IZHT, EINECS 206-982-9, NSC 96965, BRN 0746197, Anhydrid kyseliny trifluoroctove [Czech], NSC-96965, DTXSID90861920, EC 206-982-9, Acetic acid, 2,2,2-trifluoro-, 1,1′-anhydride, DTXCID90810771, Acetic acid, trifluoro, anhydride, Acetic acid, 2,2,2trifluoro, 1,1’anhydride, 206-982-9, TFAA, 2,2,2-trifluoroacetic anhydride, trifluoro acetic anhydride, (2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate, Trifluoroaceticanhydride, 2,2,2-trifluoroacetyl 2,2,2-trifluoroacetate, MFCD00000416, TRIFLUOROACETYL 2,2,2-TRIFLUOROACETATE, trifluoracetic anhydride, UNII-5ENA87IZHT, C4F6O3, trifiuoroacetic anhydnde, trifloroacetic anhydride, trifluoroactic anhydride, trifluroacetic anhydride, CF3COOCOCF3, triflouroacetic anhydride, trifluoroacteic anhydride, WLN: FXFFVOVXFFF, SCHEMBL52, trifluoro-acetic anhydride, trifluoroacetic anhyd ride, trifluoroaceticacidanhydride, tri-fluoro acetic anhydride, trifluoroacetic acidanhydride, trifluoroaceticacid anhydride, bis(trifluoroacetic)anhydride, trifloroacetic acid anhydride, trifluoracetic acid anhydride, trifluroacetic acid anhydride, CF3C(O)OC(O)CF3, trifluoroacetic acid-anhydride, (CF3CO)2O, O(COCF3)2, trifluoro acetic acid anhydride, trifluoro-acetic acid anhydride, (CF3 CO)2O, Trifluoroacetic anhydride, 99%, tri fluoro acetic acid anhydride, 2.2.2-trifluoroacetic anhydride, QAEDZJGFFMLHHQ-UHFFFAOYSA-, BCP08645, CS-B0891, NSC96965, SBB061685, STL299664, 2,2,2-trifluoroacetic acid anhydride, AKOS000121328, 2,2,2-trifluoro-acetic acid anhydride, FT16186, BP-11375, LS-12969, DB-004104, DB-049641, NS00006815, ST51047676, T0433, EN300-19297, D92342, (2,2,2-Trifluoroacetyl)2,2,2-trifluoroacetate, (2,2,2-trifluoroacetyl)-2,2,2-trifluoroacetate, Q411501, Trifluoroacetic anhydride, purum, >=99.0% (GC), Trifluoroacetic anhydride, ReagentPlus(R), >=99%, F0001-1151, Trifluoroacetic anhydride, for GC derivatization, >=99.0% (GC), InChI=1/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10

Application

Trifluoroacetic anhydride is primarily used as a powerful acylating agent in organic synthesis, enabling the introduction of trifluoroacetyl groups into various substrates. It serves as a key reagent in peptide synthesis for amino acid activation and N-terminal deprotection. The compound is also employed in analytical chemistry as a derivatization agent for GC-MS analysis of alcohols and amines. Additionally, it finds application in the preparation of trifluoromethylated compounds and as a solvent or catalyst in specialized reactions.

Safety and Hazards

GHS Hazard Statements

• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (21.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H332 (93%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H361d (18.4%): Suspected of damaging the unborn child [Warning Reproductive toxicity]
• H412 (51.8%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P203, P260, P261, P264, P264+P265, P271, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1A (100%)
• Eye Dam. 1 (21.9%)
• Acute Tox. 4 (93%)
• Repr. 2 (18.4%)
• Aquatic Chronic 3 (51.8%)

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