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

A12174 tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

Codice CAS
69739-34-0
Sinonimi
tert-Butyldimethylsilyl triflate
TBDMS-OTf

Dimensioni Prezzo ($) Quantità Disponibilità
5g 57,37
25g 210,60
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tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

MDL
MFCD00000405
EINECS
274-102-0

Proprietà chimiche

Formula
C7H15F3O3SSi
Peso formula
264.34
Punto di ebollizione
65-67°/12mm
Punto di infiammabilità
36°(96°F)
Densità
1.151
Indice di rifrazione
1.3860
Sensibilità
Moisture Sensitive
Solubilità
Slightly miscible with chloroform.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H314-H318-H226

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

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
2370068
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
No

Raccomandato

  • A12535

    Trimethylsilyl trifluoromethanesulfonate, 99%
  • A13064

    tert-Butyldimethylchlorosilane, 97%
  • A18012

    Oxalyl chloride, 98%
  • L14477

    Triethylsilyl trifluoromethanesulfonate, 98%
  • 44223

    Zinc bromide, anhydrous, 99.999% (metals basis)

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