Description

2-(Trimethylsilyl)phenyl trifluoromethanesulfonate (CAS No. 88284-48-4) is a high-purity organosilicon reagent with the molecular formula C₁₀H₁₃F₃O₃SSi. This specialized compound features a trimethylsilyl group ortho-positioned to a highly reactive trifluoromethanesulfonate (triflate) leaving group, making it an exceptionally versatile intermediate in advanced organic synthesis. The triflate group’s superior leaving ability enables efficient nucleophilic substitution reactions, while the sterically hindered silyl moiety provides unique reactivity patterns. Supplied as a moisture-sensitive liquid under inert atmosphere packaging, this reagent is ideal for palladium-catalyzed cross-couplings, Lewis acid-mediated transformations, and stereoselective C-C bond formations. Our product undergoes rigorous QC testing (GC, NMR, moisture analysis) to ensure ≥98% purity for demanding synthetic applications in pharmaceutical development, materials science, and asymmetric catalysis research.

Properties

• CAS Number: 88284-48-4
• Complexity: 381
• IUPAC Name: (2-trimethylsilylphenyl) trifluoromethanesulfonate
• InChI: InChI=1S/C10H13F3O3SSi/c1-18(2,3)9-7-5-4-6-8(9)16-17(14,15)10(11,12)13/h4-7H,1-3H3
• InChI Key: XBHPFCIWRHJDCP-UHFFFAOYSA-N
• Exact Mass: 298.03067647
• Molecular Formula: C10H13F3O3SSi
• Molecular Weight: 298.36
• SMILES: C[Si](C)(C)C1=CC=CC=C1OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 298.03067647
• Synonyms: 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate, 88284-48-4, DTXSID00391985, DTXCID50342846, 629-383-8, 2-(Trimethylsilyl)phenyl Triflate, (2-trimethylsilylphenyl) trifluoromethanesulfonate, MFCD00799598, 2-(Trimethylsilyl)phenyltrifluoromethanesulfonate, C10H13F3O3SSi, (TRIMETHYLSILYL)PHENYL TRIFLATE, Methanesulfonic acid, trifluoro-, 2-(trimethylsilyl)phenyl ester, SCHEMBL1713611, BCP10118, AKOS015856668, CS-W007378, DS-16426, SY057456, DB-023683, T2089, 2-(trimethylsilyl)phenyl trifluoromethane-sulfona, 2-(trimethylsilyl)phenyl trifluoromethane sulfonate, 2-(trimethylsilyl)phenyl trifluoro-methane sulfonate, 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate, 97%, Trifluoromethanesulfonic Acid 2-(Trimethylsilyl)phenyl Ester

Application

This reagent serves as a key building block in transition metal-catalyzed reactions, particularly for constructing biaryl systems through Suzuki-Miyaura couplings. The ortho-silyl group directs metalation while the triflate enables subsequent cross-coupling, making it valuable for synthesizing sterically hindered pharmaceutical intermediates. In materials science, it functions as a precursor for silicon-containing conjugated polymers. The compound also finds use in developing silicon-tethered substrates for radical cyclization studies.

Safety and Hazards

GHS Hazard Statements

• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1B (100%)
• Eye Dam. 1 (100%)

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