Description

2,3,5-Trimethylphenyl trifluoromethanesulfonate (CAS No. 209684-76-4) is a high-purity organic sulfonate ester with the molecular formula C₁₀H₁₁F₃O₃S. This compound is widely utilized as a versatile reagent in synthetic organic chemistry, particularly in electrophilic aromatic substitution reactions and as a precursor for advanced intermediates. Its triflate group (–OSO₂CF₃) serves as an excellent leaving group, enabling efficient coupling reactions in cross-coupling methodologies (e.g., Suzuki, Heck, and Stille reactions). The 2,3,5-trimethylphenyl moiety enhances steric and electronic control in regioselective transformations. Supplied as a clear to pale-yellow liquid or low-melting solid, this reagent is rigorously tested for purity (typically ≥95% by GC or NMR) and is packaged under inert conditions to ensure stability. Ideal for pharmaceutical, agrochemical, and materials science research.

Properties

• CAS Number: 209684-76-4
• Complexity: 358
• IUPAC Name: (2,3,5-trimethylphenyl) trifluoromethanesulfonate
• InChI: InChI=1S/C10H11F3O3S/c1-6-4-7(2)8(3)9(5-6)16-17(14,15)10(11,12)13/h4-5H,1-3H3
• InChI Key: LHQZARNRZVJSBM-UHFFFAOYSA-N
• Exact Mass: 268.03809987
• Molecular Formula: C10H11F3O3S
• Molecular Weight: 268.25
• SMILES: CC1=CC(=C(C(=C1)OS(=O)(=O)C(F)(F)F)C)C
• Topological: 51.8
• Monoisotopic Mass: 268.03809987
• Synonyms: 2,3,5-Trimethylphenyl trifluoromethanesulfonate, 209684-76-4, (2,3,5-trimethylphenyl) trifluoromethanesulfonate, 2,3,5-TrimethylphenylTrifluoromethanesulfonate, Trifluoromethanesulfonic Acid 2,3,5-Trimethylphenyl Ester; 1,1,1-Trifluoromethansulfonic Acid 2,3,5-Trimethylphenyl Ester;, starbld0021171, SCHEMBL6740755, Methanesulfonic acid, trifluoro-, 2,3,5-trimethylphenyl ester

Application

2,3,5-Trimethylphenyl trifluoromethanesulfonate is a key reagent in palladium-catalyzed cross-coupling reactions for constructing complex biaryl systems. It is employed in the synthesis of liquid crystals, OLED materials, and pharmaceutical intermediates due to its robust triflate leaving group. Researchers also use it to introduce trimethylphenyl motifs into polymers or small molecules for steric tuning.

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