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226149 Sigma-Aldrich

tert-Butyldimethylsilyl trifluoromethanesulfonate

reagent grade, 98%

Synonym: TBDMS triflate, Trifluoromethanesulfonic acid tert-butyldimethylsilylester

  • CAS Number 69739-34-0

  • Linear Formula CF3SO3Si(CH3)2C(CH3)3

  • Molecular Weight 264.34

  •  Beilstein/REAXYS Number 2370068

  •  EC Number 274-102-0

  •  MDL number MFCD00000405

  •  PubChem Substance ID 24853546

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Protecting and Derivatizing Reagents, Protection and Derivatization, Silicon-Based, Synthetic Reagents More...
Quality Level   200
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.)
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

Description

Packaging

1, 5, 25 g in glass bottle

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
RIDADR 
UN 2920 3(8) / PGII
WGK Germany 
WGK 3
Flash Point(F) 
98.6 °F - closed cup
Flash Point(C) 
37 °C - closed cup
Protocols & Articles

Articles

Activating Reagents and Protecting Groups

The use of activating agents and protecting groups in organic synthesis is necessary to prevent unwanted side reactions from occurring when using other common reagents such as oxidizing or reducing a...
Chemfiles Volume 1 Article 3
Keywords: Organic synthesis

Peer-Reviewed Papers
15

References

Related Products

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Product #

Description

Add to Cart

394882 N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide, >97%
190500 tert-Butyldimethylsilyl chloride, reagent grade, 97%
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384429 tert-Butyldimethylsilyl chloride solution, 1.0 M in methylene chloride
372951 tert-Butyldimethylsilyl chloride solution, 1.0 M in THF
250236 1-(tert-Butyldimethylsilyl)imidazole, ≥95%
06735 tert-Butyldimethylsilyl chloride, for GC derivatization, LiChropur, ≥99.0% (GC)
56563 tert-Butyldimethylsilyl trifluoromethanesulfonate, for GC derivatization, LiChropur, ≥98.0% (T)
77626 N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide, for GC derivatization, LiChropur, ≥99.0% (GC)
00942 N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide with 1% tert-Butyldimethylchlorosilane, for GC derivatization, LiChropur, ≥95.0% (GC)
44795 N,O-Bis(tert-butyldimethylsilyl)acetamide, for GC derivatization, LiChropur, ≥98.0% (GC)
08168 Timestrip Plus 8 °C

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