2224-33-1

Basic information

• Product Name: Vinyltris(methylethylketoxime)silane
• Synonyms: 2-Butanone,O,O’,O’’-(ethenylsilylidyne)trioxime;Tri(2-butaneneoxime)vinylsilane;vinyltris(2-butylidenaminooxy)silane;Vinyltris(methylethylketoxime)silane;VINYLTRIS(METHYLETHYLKETOXIMINE)SILANE;VINYLTRIS(METHYLETHYLKETOXIMINO)SILANE;butan-2-one O,O',O''-(vinylsilylidyne)trioxime;VINYL TRIS-(METHYL ETHYL KETOXIMO)SILANE
• CAS NO: 2224-33-1
• Molecular Formula: C₁₄H₂₇N₃O₃Si
• Molecular Weight: 313.47
• EINECS: 218-747-8
• Product Categories: Oximino;Silicone series;Crosslinkers;Crosslinking Agents;Oximino Silanes
• Mol File: 2224-33-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: -22°C
• Boiling Point: 115 °C
• Flash Point: 90°C
• Appearance: colorless or yellowish transparent liquid
• Density: 0.982
• Vapor Pressure: 0.000237mmHg at 25°C
• Refractive Index: 1.4543-1.4553
• Water Solubility: 36.63g/L
• CAS DataBase Reference: Vinyltris(methylethylketoxime)silane(CAS DataBase Reference)
• NIST Chemistry Reference: Vinyltris(methylethylketoxime)silane(2224-33-1)
• EPA Substance Registry System: Vinyltris(methylethylketoxime)silane(2224-33-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1993
• TSCA: Yes
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 2224-33-1(Hazardous Substances Data)

Usage

Description

Vinyl Tris(methylethylketoxime)silane (VOS) is a clear and almost colorless fluid with a typical smell (MEKO). It readily hydrolyzes upon contact with moisture. It is used as a neutral curing agent in silicone sealant formulations. In most cases Vinyl Tris(methylethylketoxime)silane is used in combination with METHYLTRIS(METHYLETHYLKETOXIME)SILANE. Compared to formulations based on methyloxime silanes only, the use of combinations containing methyl- and vinyloxime silanes leads to a shorter skin formation time of the silicone sealant without a reduction of the curing time. The ability of the sealant to withstand stress early, required for a certain elasticity and tear resistance, is achieved.

Chemical Properties

Colorless or yellowish transparent liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C14H27N3O3Si/c1-8-12(5)15-18-21(11-4,19-16-13(6)9-2)20-17-14(7)10-3/h11H,4,8-10H2,1-3,5-7H3/b15-12+,16-13+,17-14+

Synthetic route

ethyl methyl ketone oxime (96-29-7) + trichlorovinylsilane (75-94-5) → tris(1-methylpropylideneaminooxy)(vinyl)silane (2224-33-1)

Conditions	Yield
With triethylamine In benzene

C10H23N3O3Si + C12H25N3O3Si → tris(2-aminoethoxy)(vinyl)silane (15942-83-3) + tris(1-methylpropylideneaminooxy)(vinyl)silane (2224-33-1)

Conditions	Yield
at 60℃; Equilibrium constant;

tris(1-methylpropylideneaminooxy)(vinyl)silane (2224-33-1) + 4-Fluoronitrobenzene (350-46-9) → O-(p-nitrophenyl)-methylethylketone oxime (13680-06-3)

Conditions	Yield
With tetrabutyl ammonium fluoride at 80℃;	97%

3-aminopropyltriethoxysilane (919-30-2) + tris(1-methylpropylideneaminooxy)(vinyl)silane (2224-33-1) → C12H24N2O3Si (86517-79-5) + C11H26N2O3Si (173608-43-0) + C13H29N3O3Si (173608-44-1) + amine propyl tris(methylethylketoxime)silane (144672-43-5)

Conditions	Yield
at 60℃; for 4h; Product distribution;

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + tris(1-methylpropylideneaminooxy)(vinyl)silane (2224-33-1) → C8H17NO3Si (123525-80-4) + C9H22N2O3Si (173608-42-9) + C11H22N2O3Si (123525-81-5) + C12H27N3O3Si (113996-35-3)

Conditions	Yield
at 60℃; for 4h; Product distribution;

tris(2-aminoethoxy)(vinyl)silane (15942-83-3) + tris(1-methylpropylideneaminooxy)(vinyl)silane (2224-33-1) → C10H23N3O3Si + C12H25N3O3Si

Conditions	Yield
at 60℃; Equilibrium constant; Product distribution;

tris(1-methylpropylideneaminooxy)(vinyl)silane (2224-33-1) + [1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane (1760-24-3) → C8H17NO3Si (123525-80-4) + C11H22N2O3Si (123525-81-5) + C11H27N3O3Si (1134640-18-8) + C14H32N4O3Si (1134640-19-9)

Conditions	Yield
at 60℃; for 4h; Product distribution;

Upstream product

• 96-29-7 ethyl methyl ketone oxime 
• 75-94-5 trichlorovinylsilane 

Downstream Products

• 13680-06-3 O-(p-nitrophenyl)-methylethylketone oxime 

Relevant articles and documents

Reaction of organylalkoxysilanes with ethanolamine and disproportionation of transetherification products

Transetherification of organylalkoxysilanes with monoethanolamine was carried out. Disproportionation in mixtures containing organylalkoxysilanes with an amino group in the substituent was studied by means of NMR spectroscopy. It was shown that the disproportionation rate decreases with increase size of substituents on the silicon atom. The equilibrium composition of disproportionation products corresponds to the normal statistical distribution, except for mixtures containing tris(1-methylpropylideneaminooxy)(vinyl)-silane.