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27607-77-8 - Trimethylsilyl trifluoromethanesulfonate, 99% - TMS-OTf - Trifluoromethanesulfonic acid trimethylsilyl ester - A12535 - Alfa Aesar

A12535 Trimethylsilyl trifluoromethanesulfonate, 99%

CAS 번호
27607-77-8
동의어
TMS-OTf
Trifluoromethanesulfonic acid trimethylsilyl ester

사이즈 가격 ($) 수량 재고 여부
10g 32.20
50g 109.00
250g 436.00
장바구니에 추가 대량 견적에 추가 항목 보기

Trimethylsilyl trifluoromethanesulfonate, 99%

MDL
MFCD00000406
EINECS
248-565-4

화학적 특성

화학식
(CH3)3SiSO3CF3
화학 식량
222.26
비등점
39-40°/12mm
인화점
25°(77°F)
밀도
1.225
굴절률
1.3600
감도
Moisture Sensitive
용해도
Miscible with aliphatic, aromatic hydrocarbons, haloalkanes and ethers. Immiscible with water.

용도

Trimethylsilyl trifluoromethanesulfonate is used to prepare powerful Lewis acid, difluoroboron triflate etherate in acetonitrile solvent. It is also used as a reagent in a Dieckmann-like cyclization of ester-imides and diesters. Further, it is used in the conversion of carbonyl compounds to their enol ethers. It is also employed for chemical glycosylation reactions. Its reactivity is similar to trimethylsilyl chloride and is also involved in organic synthesis.

참고

Moisture and air sensitive. Store in a cool place. Incompatible with strong oxidizing agents and strong bases.

참조 문헌

Trialkylsilyl perfluoroalkanesulfonates are highly reactive silylating agents (see Appendix 4) and Lewis acids: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).

Amides can be N,O-disilylated with TMSOTf: Org. Synth. Coll., 9, 516 (1998). For conversion of carbonyl compounds to silyl enol ethers, see, e.g.: J. Org. Chem., 58, 1449 (1993); Org. Synth. Coll., 9, 548 (1998). The reaction rate in triethylamine is almost 109 times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980).

In general, TMSOTf has a much greater tendency to give C-silylation than TMS chloride. With esters C-silylation usually predominates: Synthesis, 867 (1977); Liebigs Ann. Chem., 816 (1983). Nitriles are C-silylated: Synthesis, 636 (1977); Synth. Commun., 18, 2111 (1988). Electron-rich alkenes, e.g. ketene acetals, as well as electron-rich aromatics such as indoles and pyrroles also undergo C-silylation: Synthesis, 928, 929 (1984):

tert-Butyl esters are cleaved directly to trimethylsilyl esters. Benzyl esters are unaffected, permitting selective cleavage: Synthesis, 545 (1980).

TMSOTf has numerous applications as a Lewis acid catalyst, notably in mediating, under very mild conditions, crossed aldol condensations between silyl enol ethers and acetals: J. Am. Chem. Soc., 102, 3248 (1980); Tetrahedron, 44, 4259 (1988); Org. Synth. Coll., 9, 642 (1998).

For a brief feature on uses of the reagent, see: Synlett, 1940 (2003).

Downey, C. W.; Poff, C. D.; Nizinski, A. N. Friedel-Crafts hydroxyalkylation of indoles mediated by trimethylsilyl trifluoromethanesulfonate. J. Org. Chem. 2015, 80 (20), 10364-10369.

Kendale, J. C.; Valentin, E. M.; Woerpel, K. A. Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C-and O-Glycosylations. Org. Lett. 2014, 16 (14), 3684-3687.

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

Merck
14,9719
바일슈타인
1868911
위험 등급
3
포장 그룹
III
통합 관세 코드
2931.90
TSCA(독성물질규제법)"
Yes

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