Description

2,5-Bis(trimethylsilyl)-1,4-phenylene Bis(trifluoromethanesulfonate) (CAS No. 613676-07-6) is a high-purity organosilicon compound with the molecular formula C₁₄H₂₀F₆O₆S₂Si₂. This specialized reagent features a phenylene core functionalized with two trifluoromethanesulfonate (triflate) groups and two trimethylsilyl (TMS) moieties, making it a valuable building block for advanced organic synthesis and materials science applications. The triflate groups are excellent leaving groups, while the TMS groups provide steric protection and influence electronic properties. Supplied as a stable solid with >95% purity (GC), this compound is ideal for use in cross-coupling reactions, polymer chemistry, and as a precursor for functional materials. Packaged under inert gas to ensure stability, it is suitable for researchers in pharmaceutical development, catalysis, and advanced material design.

Properties

• CAS Number: 613676-07-6
• Complexity: 746
• IUPAC Name: [4-(trifluoromethylsulfonyloxy)-2,5-bis(trimethylsilyl)phenyl] trifluoromethanesulfonate
• InChI: InChI=1S/C14H20F6O6S2Si2/c1-29(2,3)11-7-10(26-28(23,24)14(18,19)20)12(30(4,5)6)8-9(11)25-27(21,22)13(15,16)17/h7-8H,1-6H3
• InChI Key: BZSLFYMKJPECFT-UHFFFAOYSA-N
• Exact Mass: 518.01440274
• Molecular Formula: C14H20F6O6S2Si2
• Molecular Weight: 518.6
• SMILES: C[Si](C)(C)C1=CC(=C(C=C1OS(=O)(=O)C(F)(F)F)[Si](C)(C)C)OS(=O)(=O)C(F)(F)F
• Topological: 104
• Monoisotopic Mass: 518.01440274
• Synonyms: 2,5-bis(trimethylsilyl)-1,4-phenylene bis(trifluoromethanesulfonate), 613676-07-6, 835-742-1, [4-(trifluoromethylsulfonyloxy)-2,5-bis(trimethylsilyl)phenyl] trifluoromethanesulfonate, MFCD29067307, BZSLFYMKJPECFT-UHFFFAOYSA-N, AS-84263, B5559, D89145, 1,4-Bis(trimethylsilyl)phenyl-2,5-bis(triflate), 2,5-bis(trimethylsilyl)-1,4-phenylenebis(trifluoromethanesulfonate), 2,5-bis(trimethylsilyl)-1,4-phenylenyl bis(trifluoromethanesulfonate)

Application

This compound serves as a versatile intermediate in organic synthesis, particularly in palladium-catalyzed cross-coupling reactions where its triflate groups act as excellent leaving groups. It is used in the preparation of conjugated polymers and organic electronic materials due to its ability to form stable intermediates. Researchers also employ it in the synthesis of silicon-containing aromatic compounds for advanced material applications.

Safety and Hazards

GHS Hazard Statements

• H290 (100%): May be corrosive to metals [Warning Corrosive to Metals]
• 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

• P234, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P390, P405, P406, and P501

Hazard Classes and Categories

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

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