85272-31-7

Basic information

• Product Name: DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
• Synonyms: TRIFLUOROMETHANESULFONIC ACID DI-TERT-BUTYLSILYLENE ESTER;DI-T-BUTYLSILYLBIS(TRIFLUOROMETHANESULFONATE);DI(T-BUTYL)SILYL BIS(TRIFLUOROMETHANESULPHONATE);DI-T-BUTYLSILYL DITRIFLATE;DI-TERT-BUTYLBIS(TRIFLUOROMETHANESULFONYLOXY)SILANE;DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE);DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULPHONATE);DI-TERT-BUTYLSILYL DITRIFLATE
• CAS NO: 85272-31-7
• Molecular Formula: C₁₀H₁₈F₆O₆S₂Si
• Molecular Weight: 440.45
• EINECS: 2017-001-1
• Product Categories: Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Silyl Esters;Si-O Compounds;Synthetic Organic Chemistry
• Mol File: 85272-31-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 73-75 °C0.35 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: /
• Density: 1.352 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.398(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: sol most common organic solvents.
• Stability: Moisture Sensitive
• BRN: 3569211
• CAS DataBase Reference: DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE)(CAS DataBase Reference)
• NIST Chemistry Reference: DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE)(85272-31-7)
• EPA Substance Registry System: DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE)(85272-31-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 85272-31-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to yellow liquid

Physical properties

bp 73–75°C/0.35 mmHg; d 1.208 g cm?3.

Uses

Different sources of media describe the Uses of 85272-31-7 differently. You can refer to the following data:
1. Di-t-butylsilyl bis(trifluoromethanesulfonate) is a reagent for the selective protection of polyhydroxy compounds. This reagent reacts with 1,2-, 1,3-, and 1,4-diols under mild conditions to give the corresponding dialkylsilylene derivatives in high yield (0–50°C, 79–96%). Deprotection is conveniently achieved by using aqueous hydrofluoric acid in acetonitrile (eq 1).Unlike di-t-butyldichlorosilane, this reagent reacts with hindered alcohols. Even pinacol reacts to give the silylene derivative (100°C, 24 h, 70%). Di-t-butylsilylene derivatives of 1,2-diols are more reactive than those of 1,3- and 1,4-diols and undergo rapid hydrolysis (5 min) in THF/H2O at pH 10, while the 1,3- and 1,4- derivatives are unaffected at pH 4–10 (22°C) for several hours. This protecting group is stable under the conditions of PDC oxidation of alcohols (CH2Cl2, 25?C, 27 h) and tosylation of alcohols (pyridine, 25°C, 27 h).The reagent has seen limited use for the protection of alcohols but has been used to protect nucleosides (eq 2).The procedure consists of sequential addition of the ditriflate and triethylamine to the nucleoside in DMF. The choice of solvent is critical.
2. Protecting group reagent for 1,3-diols used recently in a synthesis of N-homoceramides. Also used for selective α-galactosylation in the synthesis of α-galactosyl ceramides.

Preparation

by the treatment of di-t-butylchlorosilane with trifluoromethanesulfonic acid, followed by distillation (71% yield).

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 56310-18-0 di-tert-butylchlorosilane 
• 18395-90-9 Di-tert-butyldichlorosilane 

Downstream Products

• 215384-50-2 di-tert-butylbis(3,4-dimethoxyphenoxy)silane 
• 321992-53-4 (3R,4R,5R,6S)-7-benzyloxy-2,4,6-trimethyl-3,5-[[bis(1,1-dimethylethyl)-silylene]dioxy]-1-heptene 
• 321995-79-3 (2R,3S,4R,5R,6R)-1,7-dibenzyloxy-2,4,6-trimethyl-3,5-[[bis(1,1-dimethylethyl)-silylene]dioxy]-heptane 
• 321995-82-8 (2S,3S,4S,5S,6R)-1,7-dibenzyloxy-2,4,6-trimethyl-3,5-[[bis(1,1-dimethylethyl)-silylene]dioxy]-heptane 
• 402571-19-1 2-[(1S,2S,3R,4R,5R,6S,7R,9S)-9-((4S,5R,6S)-2,2-Di-tert-butyl-6-ethyl-5-methyl-[1,3,2]dioxasilinan-4-yl)-6-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-8-oxo-2-triethylsilanyloxy-decyl]-6-ethyl-3,5-dimethyl-pyran-4-one 
• 138622-82-9 bis(phenylethynyl)-di-tert-butylsilane 
• 958638-81-8 O⁶-[(2,4,6-tri-isopropyl)-benzenesulfonyl]-2'-O-acetyl-3',5'-O-di-tert-butylsilanediyl guanosine 
• 753007-90-8 1-[3,5-O-(di-O-t-butylsilylene)-2-deoxy-2-hydroxymethyl-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine 
• 677767-17-8 4-methoxyphenyl O-(2-O-benzoyl-4,6-O-di-tert-butylsilylene-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 719288-97-8 (4R,5S)-4-Benzyloxymethyl-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinane 
• 612844-08-3 phenyl 2-deoxy-4,6-O-di-tert-butylsilylene-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside 
• 440359-26-2 methyl 3-O-benzyl-2,5-bis-O-di-tert-butylsilyl-α-D-arabinofuranoside 
• 457653-07-5 benzyl 2-deoxy-3,5-O-(di-tert-butylsilylene)-1,4-dithio-D-erythro-pentofuranoside 
• 442635-99-6 2,2-di-tert-butyl-4-phenethyl-[1,3,2]-dioxasilinane 

Relevant articles and documents

Synthesis and Restricted Conformation of 3',5'-O-(Di-t-butylsilanediyl)ribonucleosides

The reaction of ribonucleosides with di-t-butylsilyl diester such as dinitrate, diperchlorate and ditriflate in DMF gave selectively 3',5'-O-(di-t-butylsilanediyl)ribonucleosides in high yield.The conformation analysis by 1H NMR spectroscopy and X-ray crystallography showed that the product has a restricted conformation analogous to that observable in 3',5'-cyclic nucleotides.