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262021

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:
85272-31-7
Molecular Weight:
440.45
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
24855853
MDL number:
MFCD00010581
Beilstein/REAXYS Number:
3569211
Assay:
97%
Form:
liquid
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Quality Segment

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

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.

hcodes

H314

pictograms

Corrosion
GHS05

signalword

Danger

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

flash_point_f

195.8 °F - closed cup

flash_point_c

91 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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