Tris(trimethylsilyl)silane

• Catalog No.: B22457
• CAS Number: 1873-77-4
• M. F.: C9H28Si4
• M. W.: 248.66062
• Purity: 97%

SYNONYMS

• Title: 三(三甲硅烷基)硅烷
• IUPAC name: 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane
• IUPAC Traditional name: 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane
• Synonyms: TTMSS

DATABASE IDS

• Merck Index: 149757
• MDL Number: MFCD00077893
• Beilstein Number: 1923953
• EC Number: 000-000-0
• CAS Number: 1873-77-4

PROPERTIES

• Purity: 97%
• Boiling Point: 82-84°C/12mm
• Density: 0.806
• Flash Point: 55°C(131°F)
• Refractive Index: 1.4900
• GHS Hazard statements: H226-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-36/37/38
• Safety Statements: 26-37-60
• Storage Warning: Light Sensitive
• TSCA Listed: 否
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: II

REFERENCES

• Alkyl and cycloalkyl acid chlorides undergo hydrodechlorocarbonylation to hydrocarbons in high yield: Tetrahedron Lett., 33, 1787 (1992).
• 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.
• 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).
• 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).