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Sigma-Aldrich

Tris(trimethylsilyl)silane

97%

Synonym(s):

1,1,1,3,3,3-Hexamethyl-2-trimethylsilyl-trisilane, TTMSS

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About This Item

Linear Formula:
[(CH3)3Si]3SiH
CAS Number:
Molecular Weight:
248.66
Beilstein:
1923953
MDL number:
UNSPSC Code:
12161700
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

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

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

131.0 °F - closed cup

Flash Point(C)

55 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Synlett, 91-91 (1990)
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)

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