Description

1-Cyclohexenyl trifluoromethanesulfonate (CAS No. 28075-50-5) is a high-purity, organosulfur compound with the molecular formula C₇H₉F₃O₃S. This reagent, also known as cyclohexenyl triflate, is a versatile trifluoromethanesulfonate ester widely used in organic synthesis and pharmaceutical research. It features a reactive cyclohexenyl group bonded to a triflyl (trifluoromethanesulfonyl) moiety, making it an excellent electrophile for nucleophilic substitution reactions, cross-coupling processes, and as a precursor for cyclohexenyl derivatives. The compound is supplied as a clear to pale-yellow liquid with high chemical stability when stored under inert conditions. Ideal for laboratory-scale applications, it is rigorously tested for purity (typically ≥95% by GC or NMR) and is packaged in amber glass vials to ensure longevity. Suitable for use under anhydrous conditions, this reagent is a valuable tool for researchers in medicinal chemistry, catalysis, and materials science.

Properties

• CAS Number: 28075-50-5
• Complexity: 323
• IUPAC Name: cyclohexen-1-yl trifluoromethanesulfonate
• InChI: InChI=1S/C7H9F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h4H,1-3,5H2
• InChI Key: WVSCRRLWRRANJY-UHFFFAOYSA-N
• Exact Mass: 230.02244980
• Molecular Formula: C7H9F3O3S
• Molecular Weight: 230.21
• SMILES: C1CCC(=CC1)OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 230.02244980
• Synonyms: 28075-50-5, 1-Cyclohexenyl trifluoromethanesulfonate, cyclohex-1-en-1-yl trifluoromethanesulfonate, cyclohexen-1-yl trifluoromethanesulfonate, cyclohexenyl triflate, Cyclohex-1-enyl trifluoromethanesulfonate, Cyclohex-1-en-1-yl trifluoromethanesulphonate, cyclohexenol triflate, MFCD06411281, NSC263694, SCHEMBL201444, CHEMBL342743, DTXSID80312855, Methanesulfonic acid, trifluoro-, 1-cyclohexen-1-yl ester, cyclohexenyl trifluoromethanesulfonate, AKOS015916119, NSC-263694, O-trifluoromethylsulfonyl-1-cyclohexenol, AS-42955, (cyclohexen-1-yl)trifluoromethyl sulfonate, 1-cyclohexen-1-yl trifluoromethanesulfonate, cyclohex-1-en-1-yltrifluoromethanesulfonate, CS-0089679, 1-Cyclohexenyl trifluoromethanesulfonate, 97%, trifluoro-methanesulfonic acid 1-cyclohexenyl ester, Trifluoromethanesulfonic acid cyclohex-1-enyl ester

Application

1-Cyclohexenyl trifluoromethanesulfonate is primarily employed as an electrophilic reagent in organic synthesis, enabling the introduction of the cyclohexenyl group into target molecules via Suzuki-Miyaura or Negishi cross-coupling reactions. It serves as a key intermediate in the preparation of cyclohexene-based pharmaceuticals, agrochemicals, and fine chemicals. The triflate group enhances reactivity in palladium-catalyzed transformations, making it useful for constructing complex cyclic frameworks. Additionally, it finds applications in polymer chemistry as a monomer for functionalized polyolefins.

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