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About This Item
Linear Formula:
(CF3SO3)2Si[C(CH3)3]2
CAS Number:
Molecular Weight:
440.45
Beilstein:
3569211
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
Quality Level
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
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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.
Application
Di-tert-butylsilyl bis(trifluoromethanesulfonate) is used:
- As a Boekelheide promoter to synthesize pyrrolidines and piperidines via intramolecular cyclization.
- As a protecting group reagent for 1,3-diols used recently in a synthesis of N-homoceramides.
- For selective α-galactosylation in the synthesis of α-galactosyl ceramides.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
195.8 °F - closed cup
Flash Point(C)
91 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Zeitschrift fur Anorganische und Allgemeine Chemie, 618, 144-144 (1992)
Di-t-butylsilyl Bis (trifluoromethanesulfonate
Snorri ST,et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis, 1-7 (2001)
Di-tert-butylsilyl Bis (trifluoromethanesulfonate)
Michalina P
Synlett, 26, 273-274 (2015)
A new sequential intramolecular cyclization based on the boekelheide rearrangement
Assunta M,et al.
European Journal of Organic Chemistry (2011)
Synlett, 2379-2379 (2006)
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