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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 번호
69739-34-0
동의어
tert-Butyldimethylsilyl triflate
TBDMS-OTf

사이즈 가격 ($) 수량 재고 여부
5g 57.60
25g 234.00
장바구니에 추가 대량 견적에 추가 항목 보기

tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

MDL
MFCD00000405
EINECS
274-102-0

화학적 특성

화학식
C7H15F3O3SSi
화학 식량
264.34
비등점
65-67°/12mm
인화점
36°(96°F)
밀도
1.151
굴절률
1.3860
감도
Moisture Sensitive
용해도
Slightly miscible with chloroform.

용도

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.

참고

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

참조 문헌

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 해저드 및 주의 설명서

해저드 설명서 (EU): H226-H314-H318

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

주의 설명서: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

기타 참조

바일슈타인
2370068
위험 등급
8
포장 그룹
II
통합 관세 코드
2931.90
TSCA(독성물질규제법)"
No

권장

  • 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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