262021

Di-tert-butylsilyl bis(trifluoromethanesulfonate)

97%

• Synonym(s): DTBS ditriflate, Di-tert-butylsilyl ditriflate, Trifluoromethanesulfonic acid di-tert-butylsilylene ester
• Linear Formula: (CF₃SO₃)₂Si[C(CH₃)₃]₂
• CAS Number: 85272-31-7
• Molecular Weight: 440.45
• Beilstein/REAXYS Number: 3569211
• MDL number: MFCD00010581
• UNSPSC Code: 12352302
• PubChem Substance ID: 24855853
• NACRES: NA.22
• form: liquid
• assay: 97%

Properties

• Quality Level: 200
• assay: 97%
• form: liquid
• refractive index: n20/D 1.398 (lit.)
• bp: 73-75 °C/0.35 mmHg (lit.)
• density: 1.352 g/mL at 25 °C (lit.)
• functional group: fluoro; triflate
• SMILES string: CC(C)(C)[Si](OS(=O)(=O)C(F)(F)F)(OS(=O)(=O)C(F)(F)F)C(C)(C)C
• InChI: 1S/C10H18F6O6S2Si/c1-7(2,3)25(8(4,5)6,21-23(17,18)9(11,12)13)22-24(19,20)10(14,15)16/h1-6H3
• InChI key: HUHKPYLEVGCJTG-UHFFFAOYSA-N

Description

General description

Di-tert-butylsilyl bis(trifluoromethanesulfonate), also known as di-tert-butylsilyl ditriflate, that easily reacts with hydroxylic solvents. It is commonly used as a protecting group for diols in oligonucleotide synthesis.[1]

Application

Di-tert-butylsilyl bis(trifluoromethanesulfonate) is used:

• As a Boekelheide promoter to synthesize pyrrolidines and piperidines via intramolecular cyclization.[2]
• As a protecting group reagent for 1,3-diols used recently in a synthesis of N-homoceramides.[3]
• For selective α-galactosylation in the synthesis of α-galactosyl ceramides.[4]

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Skin Corr. 1B
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 195.8 °F - closed cup
• flash_point_c: 91 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter