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736856

Tris(triethylsilyl)silane

Name: Tris(triethylsilyl)silane
Brand: ALDRICH

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

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Properties

form

liquid

Quality Level

100

reaction suitability

reagent type: reductant

refractive index

n20/D 1.526

density

0.887 g/mL at 25 °C

storage temp.

2-8°C

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

InChI key

WNGZMQFMMHZKBG-UHFFFAOYSA-N

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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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Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents.

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

A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides.

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

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)

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Global Trade Item Number

SKU	GTIN
736856-5G	04061833367261