Description

Ethyl 4-(Trifluoromethylsulfonyloxy)benzoate (CAS No. 125261-30-5) is a high-purity synthetic organic compound with the molecular formula C₁₀H₉F₃O₅S. This ester derivative of benzoic acid features a trifluoromethylsulfonyloxy (-OSO₂CF₃) group at the para position, making it a valuable triflate (trifluoromethanesulfonate) reagent for advanced organic synthesis and pharmaceutical research. The compound is supplied as a crystalline solid or in solution, with rigorous QC ensuring >98% purity (HPLC). Its unique structure enables versatile reactivity in cross-coupling reactions, nucleophilic substitutions, and as a precursor for functionalized aromatic systems. Ideal for Suzuki-Miyaura, Heck, and Buchwald-Hartwig reactions. Store under inert atmosphere at -20°C to prevent hydrolysis.

Properties

• CAS Number: 125261-30-5
• Complexity: 404
• IUPAC Name: ethyl 4-(trifluoromethylsulfonyloxy)benzoate
• InChI: InChI=1S/C10H9F3O5S/c1-2-17-9(14)7-3-5-8(6-4-7)18-19(15,16)10(11,12)13/h3-6H,2H2,1H3
• InChI Key: IMOXRQSICNVOFP-UHFFFAOYSA-N
• Exact Mass: 298.01227904
• Molecular Formula: C10H9F3O5S
• Molecular Weight: 298.24
• SMILES: CCOC(=O)C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F
• Topological: 78.1
• Monoisotopic Mass: 298.01227904
• Synonyms: 125261-30-5, Benzoic acid, 4-[[(trifluoromethyl)sulfonyl]oxy]-, ethyl ester, ETHYL 4-(TRIFLUOROMETHANESULFONYLOXY)BENZOATE, SCHEMBL14720856, p-(ethoxycarbonyl)phenyl triflate, DTXSID60455951, HS-7515, p-(Ethoxycarbonyl)phenyl trifluoromethanesulfonate, 4-trifluoromethylsulfonyloxybenzoic acid ethyl ester

Application

This triflate ester serves as a key electrophile in palladium-catalyzed coupling reactions for constructing biaryl systems in drug discovery. The electron-withdrawing triflyloxy group enhances reactivity in SNAr reactions with amines and thiols. Researchers utilize it to introduce para-ester functionalization in materials science applications, particularly in liquid crystal and polymer synthesis. Its stability allows for storage as a bench-stable coupling partner.

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