Description

Trifluoromethanesulfonic anhydride (CAS No. 358-23-6), also known as triflic anhydride, is a highly reactive and versatile reagent widely used in organic synthesis and industrial applications. With the molecular formula C₂F₆O₅S₂ and IUPAC name trifluoromethylsulfonyl trifluoromethanesulfonate, this compound is a potent triflating agent known for its strong electrophilic properties. It is a colorless to pale yellow liquid with exceptional stability under anhydrous conditions, making it ideal for demanding synthetic procedures.

This high-purity anhydride is rigorously tested for quality, ensuring low moisture content and minimal impurities. It is packaged under inert gas to maintain reactivity and shelf life. Suitable for use in peptide coupling, polymerization catalysts, and as a superacid precursor, it is a staple in pharmaceutical, agrochemical, and materials science research. Handle with extreme care in a controlled environment due to its corrosive and moisture-sensitive nature.

Properties

• CAS Number: 358-23-6
• Complexity: 370
• IUPAC Name: trifluoromethylsulfonyl trifluoromethanesulfonate
• InChI: InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
• InChI Key: WJKHJLXJJJATHN-UHFFFAOYSA-N
• Exact Mass: 281.90913442
• Molecular Formula: C2F6O5S2
• Molecular Weight: 282.14
• SMILES: C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
• Topological: 94.3
• Monoisotopic Mass: 281.90913442
• Physical Description: Colorless hygroscopic liquid; Clear colorless liquid;
• Vapor Pressure: 8.0 [mmHg]
• Synonyms: Trifluoromethanesulfonic anhydride, Triflic anhydride, Trifluoromethanesulphonic anhydride, triflic acid anhydride, UNII-8W034LHG1U, TRIFLATE ANHYDRIDE, EINECS 206-616-8, Methanesulfonic acid, 1,1,1-trifluoro-, 1,1′-anhydride, CHEBI:48509, DTXSID501014629, 1,1,1-trifluoromethanesulfonic acid 1,1′-anhydride, DTXCID101437174, Methanesulfonic acid, trifluoro, anhydride, TRIFLUOROMETHANESULFONIC ANHYDRIDE [MI], 1,1,1Trifluoromethanesulfonic acid 1,1’anhydride, Methanesulfonic acid, 1,1,1trifluoro, 1,1’anhydride, un3265, wjkhjlxjjjathn-uhfffaoysa-n, 358-23-6, trifluoromethanesulfonic acid anhydride, trifluoromethanesulphonic acid anhydride, Methanesulfonic acid, trifluoro-, anhydride, trifluoromethylsulfonyl trifluoromethanesulfonate, MFCD00000408, trifluoromethanesulfonyl trifluoromethanesulfonate, 8W034LHG1U, trifluoromethane sulfonic anhydride, TF2O, (trifluoromethane)sulfonyl trifluoromethanesulfonate, C2F6O5S2, trifluoromethane sulfonic acid anhydride, OTf2, Triflic anhydride;Tf2O, Triflic anhydride solution, SCHEMBL160, (Tf)2O, trifluorometansulfonic anhydrid, (CF3SO2)2O, trifloromethanesulfonic anhydride, trifluormethanesulfonic anhydride, trifluormethansulphonic anhydride, trifluoromethanesufonic anhydride, trifluoromethansulfonic anhydride, Trifluoromethylsulfonic anhydride, trifluoromethanesulfonic-anhydride, trifluoromethanesulfonyl anhydride, trifluoromethansulphonic anhydride, trifluoromethylsulphonic anhydride, Triflouromethanesulfonic anhydride, trifluormethane sulfonic anhydride, Trifluoromethanesulfonic?Anhydride, trifluoromethyl sulfonic anhydride, trifluro methanesulfonic anhydride, trifluromethane sulfonic anhydride, trifiuoromethanesulphonic anhydride, trifluorornethanesulfonic anhydride, triflouromethane-sulfonic anhydride, trifluoro methanesulfonic anhydride, trifluoro-methanesulfonic anhydride, trifluoromethane-sulfonic anhydride, trifluoromethane-sulfonic-anhydride, Trifluoromethyl sulphonic anhydride, trifluoro-methanesulphonic anhydride, trifluoromethane sulphonic anhydride, trifluoromethane-sulphonic anhydride, BCP24336, CS-B0874, trifluoromethane -sulfonic anhydride, BBL036267, STL558688, trifluormethanesulfonic acid anhydride, trifluoromethylsulfonic acid anhydride, trifluoromethanesulfonic-acid anhydride, AKOS007930319, trifluormethane sulfonic acid anhydride, trifluoro-methansulfonic acid anhydride, FT01910, GS-3207, trifluoro-methanesulfonic acid anhydride, trifluoromethane-sulfonic acid anhydride, Trifluoromethanesulfonic anyhydride [MI], trifluoro methane sulfonic acid anhydride, BP-20541, Trifluoromethanesulfonic anhydride, >=99%, DB-009868, trifluormethylsulfonyl trifluormethansulfonat, NS00041402, T1100, EN300-50306, A822989, Q6128335, Trifluoromethanesulfonic anhydride (Triflic anhydride), trifluoromethylsulfonyl tris(fluoranyl)methanesulfonate, Trifluoromethanesulfonic anhydride, purum, >=98.0% (T), trifluoromethanesulfonic acid trifluoromethylsulfonyl ester

Application

Trifluoromethanesulfonic anhydride is extensively used as a triflating agent to introduce the triflyl group (–SO₂CF₃) into organic molecules, enhancing their reactivity in cross-coupling reactions. It serves as a powerful catalyst in Friedel-Crafts acylations and alkylations due to its superacidic properties. Additionally, it is employed in the synthesis of sulfonamides, sulfonate esters, and as a dehydrating agent in esterifications and nitrations.

Safety and Hazards

GHS Hazard Statements

• H272 (51.1%): May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing solids]
• H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]
• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (51.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H335 (68.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P210, P220, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P370+P378, P403+P233, P405, and P501

Hazard Classes and Categories

• Ox. Liq. 2 (51.1%)
• Acute Tox. 4 (98.2%)
• Skin Corr. 1B (100%)
• Eye Dam. 1 (51.1%)
• STOT SE 3 (68.7%)

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