Description

Propan-2-yl 4-[(trifluoromethanesulfonyl)oxy]benzoate (CAS No. 475585-05-8) is a high-purity specialty chemical with the molecular formula C₁₁H₁₁F₃O₅S. This compound, also known by its IUPAC name propan-2-yl 4-(trifluoromethylsulfonyloxy)benzoate, is a trifluoromethanesulfonate (triflate) ester derivative of isopropyl 4-hydroxybenzoate. It features a reactive triflate leaving group, making it a valuable intermediate in organic synthesis, particularly in palladium-catalyzed cross-coupling reactions. The presence of both the electron-withdrawing triflate group and the ester functionality enhances its utility in constructing complex molecular architectures. Supplied as a crystalline solid or in solution, this reagent is rigorously tested for purity (typically ≥95% by HPLC or GC) and is packaged under inert atmosphere to ensure stability. Ideal for pharmaceutical research, materials science, and advanced synthetic chemistry applications.

Properties

• CAS Number: 475585-05-8
• Complexity: 430
• IUPAC Name: isopropyl 4-(trifluoromethylsulfonyloxy)benzoate
• InChI: InChI=1S/C11H11F3O5S/c1-7(2)18-10(15)8-3-5-9(6-4-8)19-20(16,17)11(12,13)14/h3-7H,1-2H3
• InChI Key: SMUCFWVIIMNEQK-UHFFFAOYSA-N
• Exact Mass: 312.02792911
• Molecular Formula: C11H11F3O5S
• Molecular Weight: 312.26
• SMILES: CC(C)OC(=O)C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F
• Topological: 78.1
• Monoisotopic Mass: 312.02792911
• Synonyms: 475585-05-8, Propan-2-yl 4-[(trifluoromethanesulfonyl)oxy]benzoate, DTXSID90785258

Application

Propan-2-yl 4-[(trifluoromethanesulfonyl)oxy]benzoate serves as a versatile building block in Suzuki-Miyaura and other transition metal-catalyzed cross-coupling reactions to form biaryl compounds. The triflate group acts as an excellent leaving group for nucleophilic aromatic substitution reactions. Researchers utilize this compound in the synthesis of liquid crystals and advanced organic materials due to its ability to introduce benzoate moieties with precise regiochemistry. Its stability under various conditions makes it particularly valuable for multi-step synthetic routes in medicinal chemistry.

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