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Thermo Scientific Chemicals
Tris(trimethylsilyl)silane, 97%
CAS: 1873-77-4 | C9H28Si4 | 248.66 g/mol
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Chemical Identifiers
CAS1873-77-4
Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless to pale yellow
Assay (GC)≥96.0%
Identification (FTIR)Conforms
Refractive Index1.4860-1.4925 @ 20?C
FormLiquid
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Miscible with pentane, ether, toluene and tetrahydrofuran. Sparingly miscible with acetone and acetonitrile. Immiscible with water.
Notes
Light sensitive. Incompatible with strong oxidizing agents.
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.
Solubility
Miscible with pentane, ether, toluene and tetrahydrofuran. Sparingly miscible with acetone and acetonitrile. Immiscible with water.
Notes
Light sensitive. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- 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-butyl tin 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.