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Merck

360716

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:
1873-77-4
Molecular Weight:
248.66
UNSPSC Code:
12161700
NACRES:
NA.22
PubChem Substance ID:
24861995
MDL number:
MFCD00077893
Beilstein/REAXYS Number:
1923953

Key Documents

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InChI key

SQMFULTZZQBFBM-UHFFFAOYSA-N

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

assay

97%

form

liquid

reaction suitability

reagent type: reductant

Quality Level

100

bp

73 °C/5 mmHg (lit.)

density

0.806 g/mL at 25 °C (lit.)

Related Categories

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
GHS02

signalword

Warning

hcodes

H226

pcodes

P210

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 2 petroleums + Hazardous rank III + Water insoluble liquid

fsl

360716-1G: + 360716-25G: + 360716-5G: + 360716-BULK: + 360716-VAR:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
STBK3948
STBJ9394
STBJ7106
STBJ2163
STBH5253

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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)
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
Roberto Morales-Cerrada et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(1), 296-308 (2018-09-20)
Thermal decarbonylation of the acyl compounds [Mn(CO)5 (CORF )] (RF =CF3 , CHF2 , CH2 CF3 , CF2 CH3 ) yielded the corresponding alkyl derivatives [Mn(CO)5 (RF )], some of which have not been previously reported. The compounds were fully

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