360716

Sigma-Aldrich

Tris(trimethylsilyl)silane

97%

Synonym(s):
TTMSS, 1,1,1,3,3,3-Hexamethyl-2-trimethylsilyl-trisilane
Linear Formula:
[(CH3)3Si]3SiH
CAS Number:
Molecular Weight:
248.66
Beilstein/REAXYS Number:
1923953
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

reaction suitability

reagent type: reductant

refractive index

n20/D 1.489 (lit.)

bp

73 °C/5 mmHg (lit.)

density

0.806 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)[SiH]([Si](C)(C)C)[Si](C)(C)C

InChI

1S/C9H28Si4/c1-11(2,3)10(12(4,5)6)13(7,8)9/h10H,1-9H3

Inchi Key

SQMFULTZZQBFBM-UHFFFAOYSA-N

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General description

Tris(trimethylsilyl)silane is an organosilicon generally used as a radical reducing agent for xanthates, organic halides, isocyanides, selenides, and acid chlorides. It is also used for hydrosilylation of alkenes, alkynes, and dialkyl ketones.

Application

Super Silyl Protecting Groups

Used in:
  • Hydrosilylations
  • Radical reactions
  • Reductions of acid chlorides
  • Reductions of carbon-halogen bonds
  • Hydrosilations of carbonyls

  • Another common application involves the use of the tris(trimethylsilyl)silyl (TTMSS, or super silyl) group when complexed with transition metals and main group elements

  • More recently, the super silyl group is being utilized in carbon–carbon bond forming reactions

Packaging

25 g in Sure/Seal™
5 g in glass bottle

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1993C 3 / PGIII

WGK Germany

WGK 3

Flash Point(F)

131.0 °F - closed cup

Flash Point(C)

55 °C - closed cup

Synlett, 91-91 (1990)
Tris (trimethylsilyl) silane: an efficient hydrosilylating agent of alkenes and alkynes
Kopping B, et al.
The Journal of Organic Chemistry, 57(14), 3994-4000 (1992)
Tris (trimethylsilyl) silane. A new reducing agent
Chatgilialoglu C, et al.
The Journal of Organic Chemistry, 53(15), 3641-3642 (1988)
Accounts of Chemical Research, 25, 188-188 (1992)
Tris(trimethylsilyl)silane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2007)
Articles
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