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

B22457 Tris(trimethylsilyl)silane, 97%

Numéro de CAS
1873-77-4
Synonymes
TTMSS

Conditionnement Prix ($) Quantité Disponibilité
1g 29,30
5g 82,00
25g 233,00
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Tris(trimethylsilyl)silane, 97%

MDL
MFCD00077893

Propriétés chimiques

Formule
[(CH3)3Si]3SiH
Poids moleculaire
248.67
Point d'ébullition
82-84°/12mm
Point d'éclair
55°(131°F)
Densité
0.806
Indice de réfraction
1.4900
Sensibilité
Light Sensitive
Solubilité
Miscible with pentane, ether, toluene and tetrahydrofuran. Sparingly miscible with acetone and acetonitrile. Immiscible with water.

Applications

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.

Notes

Light sensitive. Incompatible with strong oxidizing agents.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H315-H319-H335

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

Mentions de prudence: 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.

Autres références

Merck
14,9757
Beilstein
1923953
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2931.90
TSCA
No

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