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Merck
CN

226149

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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24853546
EC Number:
274-102-0
Beilstein/REAXYS Number:
2370068
MDL number:
MFCD00000405

Key Documents

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Product Name

tert-Butyldimethylsilyl trifluoromethanesulfonate, reagent grade, 98%

InChI key

WLLIXJBWWFGEHT-UHFFFAOYSA-N

InChI

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

SMILES string

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

grade

reagent grade

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.)

functional group

fluoro
triflate

storage temp.

2-8°C

Quality Level

200

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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.

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

98.6 °F - closed cup

flash_point_c

37 °C - closed cup

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCBN0162V
BCBC2558
BCBL5049V
BCBH4256V
BCBC2558V

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Tetrahedron Letters, 47, 3553-3553 (2006)
Journal of the Chemical Society. Perkin Transactions 1, 625-625 (1993)
Journal of the Chemical Society. Chemical Communications, 1280-1280 (1988)
Chemistry Letters (Jpn), 33, 438-439 (2004)
The Journal of Organic Chemistry, 58, 2287-2287 (1993)
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