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69739-34-0 - tert-Butyldimethylsilyl trifluoromethanesulfonate, 98% - tert-Butyldimethylsilyl triflate - TBDMS-OTf - A12174 - Alfa Aesar

A12174 tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

CAS Number
69739-34-0
Synonyms
tert-Butyldimethylsilyl triflate
TBDMS-OTf

Size Price ($) Quantity Availability
5g 57.37
25g 210.60
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tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

MDL
MFCD00000405
EINECS
274-102-0

Chemical Properties

Formula
C7H15F3O3SSi
Formula Weight
264.34
Boiling Point
65-67°/12mm
Flash Point
36°(96°F)
Density
1.151
Refractive Index
1.3860
Sensitivity
Moisture Sensitive
Solubility
Slightly miscible with chloroform.

Applications

tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones.

Notes

Moisture sensitive. Store in a cool place. Incompatible with strong acids.

Literature References

Powerful silylating agent (see Appendix 4) and Lewis acid; compare tert-Butyl­dimethyl­chlorosilane, A13064 and 3429. Silylation of hindered alcohols can be effected with TBDMS-OTf and 2,6-lutidine, where other reagents are unsuccessful: Tetrahedron Lett., 22, 3455 (1981).

Has been used in a sequence for the conversion of N-Boc to N-Cbz: Tetrahedron Lett., 26, 5543 (1985). For an alternative method for this transformation, see Benzyl­ 2,2,2-trichloroacetimidate, A12387.

Treatment of ɑß-unsaturated esters containing a suitably-placed ketone function with the reagent and triethylamine results in tandem intramolecular Michael-aldol reactions to give cyclobutanone derivatives: J. Am. Chem. Soc., 115, 8107 (1993).

For general reactions of trialkylsilyl perfluoroalkanesulfonates, see Trimethyl­silyl­ trifluoromethanesulfonate, A12535; reviews: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).

Cheng, B.; Trauner, D. A Highly Convergent and Biomimetic Total Synthesis of Portentol. J. Am. Chem. Soc. 2015, 137 (43), 13800-13803.

Florence, G. J.; Wlochal, J. Synthesis of the Originally Proposed Structure of Palmerolide C. Chem. Eur. J 2012, 18 (45), 14250-14254.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H226

Causes severe skin burns and eye damage. Causes serious eye damage. Flammable liquid and vapour.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
2370068
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
No

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