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262021

Sigma-Aldrich

Di-tert-butylsilyl bis(trifluoromethanesulfonate)

97%

Synonym(s):

DTBS ditriflate, Di-tert-butylsilyl ditriflate, Trifluoromethanesulfonic acid di-tert-butylsilylene ester

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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.)

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.

Pictograms

Corrosion

Signal Word

Danger

Hazard 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synlett, 2379-2379 (2006)
A new sequential intramolecular cyclization based on the boekelheide rearrangement
Assunta M,et al.
European Journal of Organic Chemistry (2011)
Di-tert-butylsilyl Bis (trifluoromethanesulfonate)
Michalina P
Synlett, 26, 273-274 (2015)
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)

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