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226149

Sigma-Aldrich

tert-Butyldimethylsilyl trifluoromethanesulfonate

reagent grade, 98%

Synonym(s):

TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester

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About This Item

Linear Formula:
CF3SO3Si(CH3)2C(CH3)3
CAS Number:
69739-34-0
Molecular Weight:
264.34
Beilstein/REAXYS Number:
2370068
EC Number:
274-102-0
MDL number:
MFCD00000405
UNSPSC Code:
12352103
PubChem Substance ID:
24853546
NACRES:
NA.22

grade

reagent grade

Quality Level

200

assay

98%

refractive index

n20/D 1.385 (lit.)

bp

65-67 °C/12 mmHg (lit.)

density

1.151 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F

InChI

1S/C7H15F3O3SSi/c1-6(2,3)15(4,5)13-14(11,12)7(8,9)10/h1-5H3

InChI key

WLLIXJBWWFGEHT-UHFFFAOYSA-N

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Application

This reagent was used to introduce a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane facilitating a room temperature Cope rearrangement to a 2-CF3-4,5-dihydrooxepin.
Together with a thiolane promotes a rapid and efficient chalcogenide-Morita-Baylis-Hillman reaction.

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signalword

Danger

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

98.6 °F

flash_point_c

37 °C

ppe

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

Certificates of Analysis (COA)

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Chemistry Letters (Jpn), 33, 438-439 (2004)
Tetrahedron Letters, 47, 3553-3553 (2006)
The Journal of Organic Chemistry, 58, 2287-2287 (1993)
Heterocycles, 29, 35-35 (1989)
Tetrahedron Letters, 27, 3227-3227 (1986)
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