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Tris(trimethylsilyloxy)ethylene

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Tris(trimethylsilyloxy)ethylene Basic information

Product Name:
Tris(trimethylsilyloxy)ethylene
Synonyms:
  • TRIS(TRIMETHYLSILOXY)ETHYLENE
  • TRIS(TRIMETHYLSILYLOXY)ETHYLENE
  • [vinyl-2-ylidenetris(oxy)]tris[trimethylsilane]
  • Trimethysiloxyethylene
  • TRIS(TRIMETHYLSILYLOXY)ETHYLENE 95%
  • Tris-(trimethoxysiloxy)-ethylene
  • 2,2,7,7-tetraMethyl-4-((triMethylsilyl)oxy)-3,6-dioxa-2,7-disilaoct-4-ene
  • 1,1,2-Tris(trimethylsilyloxy)ethene
CAS:
69097-20-7
MF:
C11H28O3Si3
MW:
292.59
EINECS:
273-864-1
Product Categories:
  • Si-O Compounds
  • Synthetic Organic Chemistry
  • Monoalkoxysilanes
  • Enol Ethers
  • Organic Building Blocks
  • Oxygen Compounds
  • Si (Classes of Silicon Compounds)
  • Silicon Compounds (for Synthesis)
Mol File:
69097-20-7.mol
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Tris(trimethylsilyloxy)ethylene Chemical Properties

Boiling point:
54-56 °C/0.1 mmHg (lit.)
Density 
0.886 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.420(lit.)
Flash point:
103 °F
storage temp. 
2-8°C
form 
Liquid
Specific Gravity
0.885
color 
Clear colorless to yellow
Water Solubility 
Insoluble
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
BRN 
1962905
CAS DataBase Reference
69097-20-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38-10
Safety Statements 
26-36-37/39-16
RIDADR 
UN 1993 3/PG 3
WGK Germany 
3
10-21
TSCA 
No
HazardClass 
3.2
PackingGroup 
III
HS Code 
29310099

MSDS

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Tris(trimethylsilyloxy)ethylene Usage And Synthesis

Chemical Properties

clear colorless to yellowish liquid

Uses

Tris(trimethylsiloxy)ethylene has been used in:

  • stereospecific synthesis of insecticide ajuqarin-IV
  • microwave-assisted synthesis of 2-hydroxy-1-phenylethanone

Preparation

Tris(trimethylsilyloxy)ethylene is prepared from the bis(trimethylsilyl) derivative of glycolic acid by either forming the enolate with Lithium Hexamethyldisilazide at -78 °C in THF and trapping with Chlorotrimethylsilane, or by the reaction with Trimethylsilyl Trifluoromethanesulfonate and Triethylamine at rt (eq 1).
Tris(trimethylsilyloxy)ethylene synthesis

storage

Tris(trimethylsilyloxy)ethylene is readily hydrolyzed in protic solvents. It should be stored in a sealed container protected from the atmosphere. Since the reaction of the reagent with carboxylic acid chlorides and aldehydes under Lewis acid catalysis in the absence of solvent is highly exothermic, large-scale preparations may require regulation of the reaction temperature either by external cooling or by controlled addition of the reactants.

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