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

B22457 Tris(trimethylsilyl)silane, 97%

Codice CAS

Dimensioni Prezzo ($) Quantità Disponibilità
1g 29,30
5g 82,00
25g 233,00
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Tris(trimethylsilyl)silane, 97%


Proprietà chimiche

Peso formula
Punto di ebollizione
Punto di infiammabilità
Indice di rifrazione
Light Sensitive
Miscible with pentane, ether, toluene and tetrahydrofuran. Sparingly miscible with acetone and acetonitrile. Immiscible with water.


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.


Light sensitive. Incompatible with strong oxidizing agents.


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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H226-H315-H319-H335

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

Dichiarazioni precauzionali: P210-P261-P280a-P280a-P240-P303+P361+P353-P305+P351+P338-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. 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 INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Classe di rischio
Gruppo di imballaggio
Codice tariffe armonizzato


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