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Tris(trimethylsilyl)silane

97%

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Synonym(s):
1,1,1,3,3,3-Hexamethyl-2-trimethylsilyl-trisilane, TTMSS
Linear Formula:
[(CH3)3Si]3SiH
CAS Number:
Molecular Weight:
248.66
Beilstein/REAXYS Number:
1923953
MDL number:
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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This Item
736856409405362824
Tris(trimethylsilyl)silane 97%

360716

Tris(trimethylsilyl)silane

Tris(triethylsilyl)silane

736856

Tris(triethylsilyl)silane

Chlorotris(trimethylsilyl)silane 97%

409405

Chlorotris(trimethylsilyl)silane

Acetyltrimethylsilane 97%

362824

Acetyltrimethylsilane

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

-

reaction suitability

-

density

0.806 g/mL at 25 °C (lit.)

density

0.887 g/mL at 25 °C

density

-

density

0.811 g/mL at 25 °C (lit.)

refractive index

n20/D 1.489 (lit.)

refractive index

n20/D 1.526

refractive index

-

refractive index

n20/D 1.411 (lit.)

bp

73 °C/5 mmHg (lit.)

bp

-

bp

-

bp

-

form

liquid

form

liquid

form

solid

form

-

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

signalword

Warning

hcodes

pcodes

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

131.0 °F - closed cup

flash_point_c

55 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Accounts of Chemical Research, 25, 188-188 (1992)
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)
Changxia Shi et al.
Science advances, 6(34), eabc0495-eabc0495 (2020-09-03)
Three types of seemingly unyielding trade-offs have continued to challenge the rational design for circular polymers with both high chemical recyclability and high-performance properties: depolymerizability/performance, crystallinity/ductility, and stereo-disorder/crystallinity. Here, we introduce a monomer design strategy based on a bridged bicyclic

Articles

Molecular monolayers made via reactions of alkenes with H-Si(111) are often referred to as “self-assembled” monolayers on silicon surfaces by analogy with thiol monolayers on gold. These monolayers are chemically robust.

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