1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane

• ChemBase ID: 148644
• Molecular Formular: C9H28Si4
• Molecular Mass: 248.66062
• Monoisotopic Mass: 248.12680702
• SMILES: C[Si](C)(C)[SiH]([Si](C)(C)C)[Si](C)(C)C
• Canonical SMILES: C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C
• InChI: InChI=1S/C9H28Si4/c1-11(2,3)10(12(4,5)6)13(7,8)9/h10H,1-9H3
• InChIKey: SQMFULTZZQBFBM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• 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; 1,1,1,3,3,3-Hexamethyl-2-trimethylsilyl-trisilane; Tris(trimethylsilyl)silane; 三(三甲硅烷基)硅烷; 三(三甲基硅基)硅烷; 三(三甲硅烷基)硅烷

Database IDs

• CAS Number: 1873-77-4
• EC Number: 000-000-0
• MDL Number: MFCD00077893
• Beilstein Number: 1923953
• Merck Index: 149757
• PubChem SID: 24861995; 24889876; 162242819
• PubChem CID: 6327365

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.2589
• LogD (pH = 7.4): 3.2589
• Log P: 3.2589
• Molar Refractivity: 52.8209 cm^3
• Polarizability: 29.036903 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 73 °C/5 mmHg(lit.); 82-84°C/12mm
• Flash Point: 131 °F; 55 °C; 55°C(131°F)
• Density: 0.806; 0.806 g/mL at 25 °C(lit.)
• Refractive Index: 1.4900; n20/D 1.489; n20/D 1.489(lit.)

Safety Information

• Storage Warning: Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; II
• Risk Statements: 10-36/37/38
• Safety Statements: 16-26-36; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥97.0% (GC); 97%
• Grade: purum
• Linear Formula: [(CH3)3Si]3SiH

DETAILS

Sigma Aldrich - 360716

Packaging
25 g in Sure/Seal™
5 g in glass bottle
Application
Super Silyl Protecting GroupsUsed in:
• Hydrosilylations1
• Radical reactions2
• Reductions of acid chlorides3
• Reductions of carbon-halogen bonds4
• Hydrosilations of carbonyls5
• Another common application involves the use of the tris(trimethylsilyl)silyl (TTMSS, or super silyl) group when complexed with transition metals and main group elements6,7
• More recently, the super silyl group is being utilized in carbon-carbon bond forming reactions8

Sigma Aldrich - 93411

General description
"Reagent of the Year 1990"
Other Notes
Efficient mediator in organic radical reactions that rivals tributyltin hydride. It is a superior reagent for ecological and practical reasons giving less unwanted reduction products9,10,4,11; In can be used in catalytic amounts in the presence of sodium borohydride; Starting material for various tris(TMS)3silyl compounds
Application
Super Silyl Protecting GroupsUsed in:
• Hydrosilylations1
• Radical reactions2
• Reductions of acid chlorides3
• Reductions of carbon-halogen bonds4
• Hydrosilations of carbonyls5
• Another common application involves the use of the tris(trimethylsilyl)silyl (TTMSS, or super silyl) group when complexed with transition metals and main group elements6,7
• More recently, the super silyl group is being utilized in carbon-carbon bond forming reactions8

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).