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226149

Sigma-Aldrich

tert-Butyldimethylsilyl trifluoromethanesulfonate

reagent grade, 98%

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Synonym(s):
TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester
Linear Formula:
CF3SO3Si(CH3)2C(CH3)3
CAS Number:
Molecular Weight:
264.34
Beilstein/REAXYS Number:
2370068
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

reagent grade

Quality Level

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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1 of 4

This Item
91741225649262021
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

density

1.151 g/mL at 25 °C (lit.)

density

1.228 g/mL at 25 °C (lit.)

density

1.228 g/mL at 25 °C (lit.)

density

1.352 g/mL at 25 °C (lit.)

bp

65-67 °C/12 mmHg (lit.)

bp

77 °C/80 mmHg (lit.)

bp

77 °C/80 mmHg (lit.)

bp

73-75 °C/0.35 mmHg (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

refractive index

n20/D 1.385 (lit.)

refractive index

n20/D 1.36 (lit.)

refractive index

n20/D 1.36 (lit.)

refractive index

n20/D 1.398 (lit.)

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_germany

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


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Journal of the Chemical Society. Chemical Communications, 1280-1280 (1988)
Chemistry Letters (Jpn), 33, 438-439 (2004)
Journal of the Chemical Society. Perkin Transactions 1, 625-625 (1993)
The Journal of Organic Chemistry, 58, 2287-2287 (1993)
Tetrahedron Letters, 27, 3227-3227 (1986)

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