91741

Trimethylsilyl trifluoromethanesulfonate

purum, ≥98.0% (T)

• Synonym(s): TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester
• Linear Formula: CF₃SO₃Si(CH₃)₃
• CAS Number: 27607-77-8
• Molecular Weight: 222.26
• Beilstein: 1868911
• EC Number: 248-565-4
• MDL number: MFCD00000406
• UNSPSC Code: 12352101
• PubChem Substance ID: 329770075
• NACRES: NA.22

Properties

• grade: purum
• Quality Level: 200
• Assay: ≥98.0% (T)
• form: liquid
• refractive index: n20/D 1.36 (lit.)
• bp: 77 °C/80 mmHg (lit.)
• density: 1.228 g/mL at 25 °C (lit.)
• functional group: fluoro; triflate
• SMILES string: C[Si](C)(C)OS(=O)(=O)C(F)(F)F
• InChI: 1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
• InChI key: FTVLMFQEYACZNP-UHFFFAOYSA-N

Description

Application

Trimethylsilyl trifluoromethanesulfonate may be used to catalyze:

• Allylation of acetals to form homoallyl ethers.
• Synthesis of 1,2-trans-glycosides.
• Conversion of alcohols to esters.
• Aminomethylation of silyl enol ethers with aminomethyl alkyl ethers.
• Glycosidation of (+)-4-demethoxyanthracyclinones.

Other Notes

Efficient silylating agent and strong Lewis acid catalyst ; Review

Safety Information

• Pictograms: GHS02,GHS05
• Signal Word: Danger
• Hazard Statements: H226,H314
• Precautionary Statements: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Flam. Liq. 3 - Skin Corr. 1B
• Supplementary Hazards: EUH014
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 77.0 °F - closed cup
• Flash Point(C): 25 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves