Description

2,2,2-Trifluoroethyl trifluoromethanesulfonate (CAS No. 6226-25-1) is a high-purity fluorinated sulfonate ester with the molecular formula C₃H₂F₆O₃S. This specialized chemical is widely used in organic synthesis, pharmaceuticals, and materials science due to its exceptional reactivity as a triflating agent. The compound features a trifluoroethyl group (-CH₂CF₃) and a trifluoromethanesulfonate (triflate, -OSO₂CF₃) moiety, making it an ideal reagent for introducing triflate groups in nucleophilic substitution reactions or as a precursor for advanced fluorinated materials.

Our product is rigorously tested to ensure ≥95% purity (GC) and is supplied in sealed, moisture-resistant packaging to maintain stability. It is compatible with anhydrous conditions and inert atmospheres, making it suitable for sensitive applications in catalysis, polymer chemistry, and electrochemistry. Synonyms include trifluoroethyl triflate, CF₃CH₂OTf, and Trifluoromethanesulfonic Acid 2,2,2-Trifluoroethyl Ester.

Key Features:

• High reactivity in SN₂ reactions and cross-coupling catalysis
• Low nucleophilicity of the triflate anion enhances leaving-group efficiency
• Stable under inert conditions but hydrolyzes in moisture
• Compatible with Grignard reagents, organolithium compounds, and transition-metal catalysts

Properties

• CAS Number: 6226-25-1
• Complexity: 254
• IUPAC Name: 2,2,2-trifluoroethyl trifluoromethanesulfonate
• InChI: InChI=1S/C3H2F6O3S/c4-2(5,6)1-12-13(10,11)3(7,8)9/h1H2
• InChI Key: RTMMSCJWQYWMNK-UHFFFAOYSA-N
• Exact Mass: 231.96288407
• Molecular Formula: C3H2F6O3S
• Molecular Weight: 232.10
• SMILES: C(C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 231.96288407
• Synonyms: 2,2,2-Trifluoroethyl trifluoromethanesulfonate, 458-390-7, 612-977-6, 6226-25-1, 2,2,2-Trifluoroethyltrifluoromethanesulfonate, 2,2,2-Trifluoroethyl triflate, Methanesulfonic acid, trifluoro-, 2,2,2-trifluoroethyl ester, Trifluoromethanesulfonic Acid 2,2,2-Trifluoroethyl Ester, MFCD00671579, 2,2,2-trifluoroethyl trifluoromethane sulfonate, 2,2,2-trifluoroethyl trifluoromethane-sulfonate, 2,2,2-Trifluoroethyl trifluoromethanesulfonate, 95%, C3H2F6O3S, Trifluoromethanesulfonic Acid 2,2,2-Trifluoroethyl Ester; 2,2,2-Trifluoroethanol Trifluoromethanesulfonate; 2,2,2-Trifluoroethyl trifluoromethanesulfonate; 2,2,2-Trifluoroethyl trifluoromethylsulfonate;, Trifluoroethyltriflate, trifluoroethyl triflate, CF3CH2OTf, trifluoroethanol triflate, CF3CH2OSO2CF3, KXY6L2J6TQ, F3CSO3CH2CF3, 2,2,2-trifluoroethyl trifluoromethanesulphonate, SCHEMBL26912, 2,2,2-trifluoroethyltriflate, 2,2,2-trifluorethyl triflate, DTXSID1073365, CS-B0885, SBB097874, trifluoroethyl trifluormethanesulfonate, AKOS005063773, trifluoroethyl trifluoromethanesulfonate, PB47912, trifluoroethyl trifluormethane sulphonate, trifluoroethyl trifluormethane-sulphonate, trifluoroethyl trifluoromethane sulphonate, trifluoroethyl trifluoromethane-sulphonate, AS-11398, T1604, 2,2,2-triflouroethyl trifluoromethanesulfonate, 2,2,2-trifluorethyl trifluoromethanesulfonate, 2,2,2-trifluoroethyl trifluoromethylsulfonate, 2,2,2-trifluoroethyl-trifluoromethylsulphonate, 2,2,2-trifluoroethyltrifluoromethanesulphonate, 2,2,2-Trifluoroethyltrifluoromethyl sulfonate, 2,2,2-trifluroethyl trifluoromethanesulfonate, 2.2.2-trifluoroethyl trifluoromethanesulfonate, EN300-31162, 2,2,2,-trifluorethyl trifluoromethanesulfonate, 2,2,2-trifluoro-ethyl trifluoromethanesulfonate, 2,2,2-trifluoroethyl trifluoromethanesul-fonate, 2,2,2-trifluoroethyl-trifluoro-methanesulfonate, 2,2,2-Trifluoroethyl-trifluoromethanesulfonate, 2,2,2-trifluoroethyl (trifluoromethyl)sulfonate, 2,2,2-trifluoroethyl trifluoromethane-sulphonate, Ethanol, 2,2,2-trifluoro-, trifluoromethanesulfonate, F0001-1665, Trifluoromethanesulfonic acid-2,2,2-trifluoroethyl ester, trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester, trifluoro-methanesulfonic acid 2,2,2-trifluoroethyl ester, trifluoro-methanesulphonic acid 2,2,2-trifluoro-ethyl ester, trifluoromethane sulfonic acid 2,2,2-trifluoroethyl ester, trifluoromethanesulfonic acid 2,2,2-trifluoro-ethyl ester, 1,1,1-trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester

2,2,2-Trifluoroethyl trifluoromethanesulfonate is primarily used as a triflating agent to convert alcohols or phenols into highly reactive triflate esters for subsequent nucleophilic displacement. In pharmaceutical research, it serves as a key intermediate for synthesizing fluorinated analogs of bioactive molecules. The compound also finds utility in polymer science for modifying fluoropolymer backbones and in electrochemical applications due to its stability in non-aqueous systems. Handle under nitrogen/argon to prevent hydrolysis.

Safety and Hazards

GHS Hazard Statements

• H301 (85.7%): Toxic if swallowed [Danger Acute toxicity, oral]
• H314 (86.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H315 (12.1%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (12.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H330 (85.7%): Fatal if inhaled [Danger Acute toxicity, inhalation]
• H335 (12.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (14.3%)
• Acute Tox. 3 (85.7%)
• Skin Corr. 1B (100%)
• Eye Dam. 1 (42.9%)
• Acute Tox. 2 (85.7%)
• Acute Tox. 4 (14.3%)
• Muta. 2 (14.3%)

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