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736856

Sigma-Aldrich

Tris(triethylsilyl)silane

Sinónimos:

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

Fórmula empírica (notación de Hill):
C18H46Si4
Número de CAS:
25436-74-2
Peso molecular:
374.90
MDL number:
MFCD19053177
UNSPSC Code:
12352001
PubChem Substance ID:
329765148
NACRES:
NA.22

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

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Synthesis of ?-Hydroxy-?-haloesters through Super Silyl Ester Directed Syn-Selective Aldol Reaction.
Oda S and Yamamoto H
Organic Letters, 15(23), 6030-6033 (2013)
Highly Stable Silyl Radicals (Et n Me3-n Si) 3Si?(n= 1? 3).
Kyushin S, et al.
Organometallics, 16(25), 5386-5388 (1997)
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)
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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