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

B22457 Tris(trimethylsilyl)silane, 97%

CAS-Nummer
1873-77-4
Synonyme
TTMSS

Größe Preis ($) Menge Verfügbarkeit
1g 29,30
5g 82,00
25g 233,00
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Tris(trimethylsilyl)silane, 97%

MDL
MFCD00077893

Chemische Eigenschaften

Formel
[(CH3)3Si]3SiH
Molmasse
248.67
Siedepunkt
82-84°/12mm
Flammpunkt
55°(131°F)
Dichte
0.806
Brechungsindex
1.4900
Sensitivität
Light Sensitive
Löslichkeit
Miscible with pentane, ether, toluene and tetrahydrofuran. Sparingly miscible with acetone and acetonitrile. Immiscible with water.

Anwendungen

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.

Bemerkungen

Light sensitive. Incompatible with strong oxidizing agents.

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H226-H315-H319-H335

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

Sicherheitshinweise: P260-P201-P280a-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves and eye/face protection. 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.

Weitere Referenzen

Merck
14,9757
Beilstein
1923953
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2931.90
TSCA
No

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