902489

Tris(trimethylsilyl)silanol

≥95%

• Synonym(s): (Hydroxy-bis(trimethylsilyl)silyl)-trimethylsilane, (TMS)₃SiOH, 1,1,1,3,3,3-Hexamethyl-2-(trimethylsilyl)trisilan-2-ol, Supersilanol
• Empirical Formula (Hill Notation): C₉H₂₈OSi₄
• CAS Number: 7428-60-6
• Molecular Weight: 264.66
• MDL number: MFCD00093727
• UNSPSC Code: 12161700
• NACRES: NA.22

Properties

• Assay: ≥95%
• form: liquid
• reaction suitability: reaction type: C-C Bond Formation
• refractive index: n/D 1.496
• density: 0.859 g/mL
• SMILES string: [Si]([Si](C)(C)C)([Si](C)(C)C)([Si](C)(C)C)O
• InChI: 1S/C9H28OSi4/c1-11(2,3)14(10,12(4,5)6)13(7,8)9/h10H,1-9H3
• InChI key: ABTWCNHNRLMBFR-UHFFFAOYSA-N

Description

Application

Under a dual catalytic copper/photoredox manifold, this supersilanol has been demonstrated by the MacMillan lab to be an excellent reagent for the trifluoromethylation of alkyl halides and aryl halides to yield alkyl-CF₃ and aryl-CF₃ in high yields. In both cases, these reactions exhibit wide substrate scope with good functional group tolerance. More specifically, a variety of 5-membered and 6-membered heteroaryl halides can be readily converted to the corresponding trifluoromethylheteroarenes under mild conditions. To be use in conjunction with dMesSCF₃ (901466) and Ir photocatalyst (902217 or 902225).

Other Notes

A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 200.3 °F
• Flash Point(C): 93.5 °C