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358-23-6 - Trifluoromethanesulfonic anhydride, 98% - Triflic anhydride - A11767 - Alfa Aesar

A11767 Trifluoromethanesulfonic anhydride, 98%

CAS 번호
358-23-6
동의어
Triflic anhydride

사이즈 가격 ($) 수량 재고 여부
10g 50.50
25g 104.00
50g 179.00
100g 326.00
250g 458.00
장바구니에 추가 대량 견적에 추가 항목 보기

Trifluoromethanesulfonic anhydride, 98%

MDL
MFCD00000408
EINECS
206-616-8

화학적 특성

화학식
C2F6O5S2
화학 식량
282.13
융점
-80°
비등점
81-83°
밀도
1.720
굴절률
1.3210
감도
Moisture Sensitive
용해도
Miscible with dichloromethane. Immiscible with hydrocarbons.

용도

Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.

참고

Moisture sensitive. Incompatible with water, strong bases, strong oxidizing agents, acids and alcohols.

참조 문헌

For examples of preparation of alkyl and aryl triflates, and use of the latter in the Stille coupling reaction, see: Org. Synth. Coll., 6, 324 (1988); 9, 553 (1998). Alkyl triflates undergo solvolysis reactions between five and seven powers of ten times more rapidly than the corresponding halides or tosylates: J. Am. Chem. Soc., 97, 6478 (1975); Angew. Chem. Int. Ed., 9, 521 (1970). For a review of the chemistry of triflate esters, see: Synthesis, 85 (1982).

Enolizable carbonyl compounds in the presence of base can be converted to vinyl (enol) triflates: Synthesis, 85 (1982); Org. Synth. Coll., 6, 757 (1988). For conditions employing preferred base, 2,6-Di-tert-butyl-4-methyl­pyridine, L14143, see: Org. Synth. Coll., 8, 97, 126 (1993). Enol triflates behave as a source of vinyl cations. For reviews, see: Angew. Chem. Int. Ed., 17, 333 (1978); Acc. Chem. Res., 11, 107 (1978); 15, 348 (1982); 21, 147 (1988).

For formation of keteniminium triflates, see N,N-Dimethyl­acetamide, A10924.

The Ritter reaction is normally most successful with tertiary alcohols. In contrast, a useful variation allows conversion of primary or secondary alcohols to amides in good yield: Tetrahedron Lett., 30, 581 (1989):

For use in the Vilsmeier formylation of less active substrates, see N,N-Dimethyl­formamide, A13547.

Triflic anhydride has also been found to promote the nitration of arenes, even deactivated ones, under mild conditions: Synthesis, 1087 (1992).

For a review of chemical transformations induced by the reagent, see: Tetrahedron, 56, 3077 (2000). For a brief feature on uses in synthesis, see: Synlett, 390 (2004).

Dadgar, M.; Kalkhorani, N. M. Efficient and practical one-pot route to synthesise quinazolin4 (3H)-ones using trifluoromethanesulfonic anhydride and 2-chloropyridine. J. Chem. Res. 2015, 39 (2), 120-122.

Huang, P. Q.; Lang, Q. W.; Wang, A. E.; Zheng, J. F. Direct reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols. Chem. Commun. 2015, 51 (6), 1096-1099.

GHS 해저드 및 주의 설명서

해저드 설명서 (EU): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

주의 설명서: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

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. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

기타 참조

바일슈타인
1813600
위험 등급
8
포장 그룹
II
통합 관세 코드
2904.99
TSCA(독성물질규제법)"
Yes
RTECS(화학물질 독성 등록)
PB2772000

권장

최근에 본 것

화학물질

화학물질

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