Description

Methyl 5-chloro-2-[(trifluoromethanesulfonyl)oxy]benzoate (CAS No. 494210-98-9) is a high-purity synthetic intermediate widely utilized in pharmaceutical and agrochemical research. This compound, with the molecular formula C₉H₆ClF₃O₅S, features a benzoate ester core functionalized with a reactive trifluoromethanesulfonyloxy (triflate) group at the 2-position and a chloro substituent at the 5-position. The triflate group serves as an excellent leaving group, enabling versatile cross-coupling reactions such as Suzuki, Stille, and Negishi couplings. Its methyl ester moiety further enhances its utility as a precursor for carboxylic acid derivatives. Supplied as a crystalline solid with ≥95% purity (HPLC), this reagent is rigorously tested for consistency and stability, making it ideal for demanding synthetic applications. Packaged under inert gas to ensure longevity, it is a critical building block for medicinal chemists and material scientists.

Properties

• CAS Number: 494210-98-9
• Complexity: 430
• IUPAC Name: methyl 5-chloro-2-(trifluoromethylsulfonyloxy)benzoate
• InChI: InChI=1S/C9H6ClF3O5S/c1-17-8(14)6-4-5(10)2-3-7(6)18-19(15,16)9(11,12)13/h2-4H,1H3
• InChI Key: IAQWISLAHGFNCH-UHFFFAOYSA-N
• Exact Mass: 317.9576566
• Molecular Formula: C9H6ClF3O5S
• Molecular Weight: 318.65
• SMILES: COC(=O)C1=C(C=CC(=C1)Cl)OS(=O)(=O)C(F)(F)F
• Topological: 78.1
• Monoisotopic Mass: 317.9576566
• Synonyms: 494210-98-9, Methyl 5-chloro-2-(trifluoromethylsulfonyloxy)benzoate, Methyl 5-chloro-2-[(trifluoromethanesulfonyl)oxy]benzoate, Benzoic acid, 5-chloro-2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester, SCHEMBL15826901, DTXSID10732623, DB-109436, A1-05440, Methyl 5-chloro-2-(((trifluoromethyl)sulfonyl)oxy)benzoate

Application

Methyl 5-chloro-2-[(trifluoromethanesulfonyl)oxy]benzoate is a key intermediate in the synthesis of bioactive molecules, particularly in the development of kinase inhibitors and antimicrobial agents. Its triflate group facilitates palladium-catalyzed cross-coupling reactions to construct complex biaryl scaffolds prevalent in drug discovery. Researchers also employ it to introduce chlorobenzoate motifs into polymers or ligands for catalysis. In agrochemistry, it serves as a precursor for herbicidal and fungicidal compounds.

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