[B22457] CAS 1873-77-4 | Tris(trimethylsilyl)silane, 97%

CAS : 1873-77-4
UN# : UN1993
MDL : MFCD00077893
Hazard Class : 3
Packing Group : III

Other name :

TTMSS

Chemical Properties

Formula : [(CH3)3Si]3SiH
Formula weight : 248.67
Boiling Point : 82-84°/12mm
Flash point : 55°(131°F)
Density : 0.806
Refractive Index : 1.4900
Sensitivity : Air Sensitive. Store under Argon. Ambient temperatures.
Form : Liquid
Solubility : Miscible with pentane, ether, toluene and tetrahydrofuran. Sparingly miscible with acetone and acetonitrile. Immiscible with water.

Literature 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-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.

Notes

Light sensitive. Incompatible with strong oxidizing agents.Other References:Beilstein: 1923953Merck: 14,9757UN#: UN1993

Grade Specifications

Grade Specifications

Hazard Statements : H226-H315-H319-H335Flammable liquid and vapour.Causes skin irritation.Causes serious eye irritation.May cause respiratory irritation.
Precautionary Statements : P210-P241-P303+P361+P353-P305+P351+P338-P405-P501aKeep away from heat/sparks/open flames/hot surfaces. – No smoking.Use explosion-proof electrical/ventilating/lighting/ 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.Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.