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1873-77-4 - Tris(trimethylsilyl)silane, 97% - TTMSS - B22457 - Alfa Aesar

B22457 Tris(trimethylsilyl)silane, 97%

CAS 번호
1873-77-4
동의어
TTMSS

사이즈 가격 ($) 수량 재고 여부
1g 29.30
5g 82.00
25g 233.00
장바구니에 추가 대량 견적에 추가 항목 보기

Tris(trimethylsilyl)silane, 97%

MDL
MFCD00077893

화학적 특성

화학식
[(CH3)3Si]3SiH
화학 식량
248.67
비등점
82-84°/12mm
인화점
55°(131°F)
밀도
0.806
굴절률
1.4900
감도
Light Sensitive
용해도
Miscible with pentane, ether, toluene and tetrahydrofuran. Sparingly miscible with acetone and acetonitrile. Immiscible with water.

용도

Tris(trimethylsilyl)silane is used in hydrosilylations of carbonyls, radical reactions, reductions of acid chlorides, and carbon-halogen bonds. It acts a mediator of radical reactions and considered to be a nontoxic substitute for tri-n-butylstannane in radical reactions. It forms complexes with transition metals and main group elements. Further, it is utilized in carbon-carbon bond forming reactions.

참고

Light sensitive. Incompatible with strong oxidizing agents.

참조 문헌

Radical-based reducing agent, e.g. for hydrodehalogenation reactions of halides to the corresponding hydrocarbons: J. Org. Chem., 56, 678 (1991); cf TBTH ( Tri-n-butyl­tin hydride, A13298 ). Reversal of the stereoselectivity observed in the TBTH reduction of gem-dichlorides has been reported: J. Am. Chem. Soc., 116, 10781 (1994).

In the presence of a free-radical initiator, ring closure reactions of bromides containing a suitably-positioned double bond can be effected: Tetrahedron Lett., 38, 8165 (1997); 39, 7267 (1998). In the presence of CO, 1,5-dienes undergo tandem silylcarbonylation and cyclization to give cyclopentanone derivatives: J. Organomet. Chem., 548, 105 (1997).

Alkyl and cycloalkyl acid chlorides undergo hydrodechlorocarbonylation to hydrocarbons in high yield: Tetrahedron Lett., 33, 1787 (1992).

Effects the hydrosilylation of alkenes and alkynes in high yield: J. Org. Chem., 57, 3994 (1992); this reaction forms the basis of a (Z) - (E) olefin interconversion via addition-elimination of the tris(TMS)silane radical: J. Org. Chem., 60, 3826 (1995).

Superior to TBTH for the radical mediated cyclization of bromo lactones, avoiding the need for very high dilutions: Heterocycles, 37, 289 (1994).

For a brief survey of uses of this reagent in Organic synthesis, see: Synlett, 1972 (2007).

For a review of organosilanes as radical-based reducing agents in synthesis, see: Acc. Chem. Res., 25, 188 (1992). See also Appendix 4.

da Silva, G. P.; Ali, A.; da Silva, R. C.; Jiang, H.; Paixão, M. W. Tris(trimethylsilyl) silane and visible-light irradiation: a new metal-and additive-free photochemical process for the synthesis of indoles and oxindoles. Chem. Commun. 2015, 51 (82), 15110-15113.

Mandhapati, A. R.; Rajender, S.; Shaw, J.; Crich, D. The Isothiocyanato Moiety: An Ideal Protecting Group for the Stereoselective Synthesis of Sialic Acid Glycosides and Subsequent Diversification. Angew. Chem. Int. Ed. 2015, 54 (4), 1275-1278.

GHS 해저드 및 주의 설명서

해저드 설명서 (EU): H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

주의 설명서: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. 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
14,9757
바일슈타인
1923953
위험 등급
3
포장 그룹
III
통합 관세 코드
2931.90
TSCA(독성물질규제법)"
No

권장

  • A10632

    Ammonium thiocyanate, 98+%
  • A11766

    Allyl bromide, 99%, stab. with 300-1000ppm Propylene oxide
  • A12132

    Ethylenediamine, 99%
  • A13298

    Tri-n-butyltin hydride, 97%, stab.
  • 89892

    Oxone®, monopersulfate

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