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Merck
CN

736856

Tris(triethylsilyl)silane

Synonym(s):

1,1,1,3,3,3-Hexaethyl-2-(triethylsilyl)trisilane, 3,4,5-Trisilaheptane, 3,3,5,5-tetraethyl-4-(triethylsilyl)

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About This Item

Empirical Formula (Hill Notation):
C18H46Si4
CAS Number:
25436-74-2
Molecular Weight:
374.90
NACRES:
NA.22
PubChem Substance ID:
329765148
UNSPSC Code:
12352001
MDL number:
MFCD19053177
Form:
liquid

Key Documents

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InChI key

WNGZMQFMMHZKBG-UHFFFAOYSA-N

SMILES string

CC[Si](CC)(CC)[SiH]([Si](CC)(CC)CC)[Si](CC)(CC)CC

InChI

1S/C18H46Si4/c1-10-20(11-2,12-3)19(21(13-4,14-5)15-6)22(16-7,17-8)18-9/h19H,10-18H2,1-9H3

form

liquid

reaction suitability

reagent type: reductant

refractive index

n20/D 1.526

density

0.887 g/mL at 25 °C

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Tris(triethylsilyl)silane can be incorporated as a directing group for various regio- and stereo-selective reactions. Hydrogen abstraction from tris(triethylsilyl)silane yields highly stable silyl radical.
Tris(triethylsilyl)silane can be used as a hydrogen atom donor reagent in chemical synthesis due to its weak Si-H bond. Hydrogen abstraction from tris(triethylsilyl)silane yields a highly stable silyl radical.
It can be used as a reagent:
  • In the radical coupling reaction to generate C-C bonds from alkyl-halogen compounds using iridium and nickel catalysts.
  • To synthesize α-arylated product via cross-electrophile coupling reaction between α-chloro carbonyl and aryl bromide in the presence of nickel and iridium catalysts.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ7129
MKCZ4133
MKCX5090
MKCX5089
MKCV8307

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Generation of Organolithium Compounds bearing Super Silyl Ester and their Application to Matteson Rearrangement.
Oda S and Yamamoto H
Angewandte Chemie (International Edition in English), 125(31), 8323-8326 (2013)
Selective Michael Reaction Controlled by Supersilyl Protecting Group.
Izumiseki A and Yamamoto H
Angewandte Chemie (International Edition in English), 127(30), 8821-8823 (2015)
Tiffany Q Chen et al.
Angewandte Chemie (International ed. in English), 58(41), 14584-14588 (2019-08-15)
Here, we demonstrate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified method for the α-arylation of diverse activated alkyl chlorides, including α-chloroketones, α-chloroesters, α-chloroamides, α-chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective for a wide variety of
Controlling stereochemistry in polyketide synthesis: 1, 3-vs. 1, 2-asymmetric induction in methyl ketone aldol additions to ?-super siloxy aldehydes.
Brady PB, et al.
Chemical Science, 4(8), 3223-3231 (2013)
Jonathan D Bell et al.
Chemical Society reviews, 50(17), 9540-9685 (2021-07-27)
Photoredox chemistry with organic or transition metal agents has been reviewed in earlier years, but such is the pace of progress that we will overlap very little with earlier comprehensive reviews. This review first presents an overview of the area
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