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Tris(triethylsilyl)silane

Synonym(e):

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

Empirische Formel (Hill-System):
C18H46Si4
CAS-Nummer:
25436-74-2
Molekulargewicht:
374.90
MDL-Nummer:
MFCD19053177
UNSPSC-Code:
12352001
PubChem Substanz-ID:
329765148
NACRES:
NA.22

Form

liquid

Eignung der Reaktion

reagent type: reductant

Brechungsindex

n20/D 1.526

Dichte

0.887 g/mL at 25 °C

Lagertemp.

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

InChIKey

WNGZMQFMMHZKBG-UHFFFAOYSA-N

Anwendung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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
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)
Selective Michael Reaction Controlled by Supersilyl Protecting Group.
Izumiseki A and Yamamoto H
Angewandte Chemie (International Edition in English), 127(30), 8821-8823 (2015)
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)
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