Vinyltris(methylethylketoxime)silane
[CAS# 2224-33-1]

Identification

• Classification: Chemical reagent >> Silane reagent
• Name: Vinyltris(methylethylketoxime)silane
• Synonyms: Vinyltris(methylethylketoximino)silane; Tri(2-butaneneoxime)vinylsilane; Vinyltris(2-butylidenaminooxy)silane
• Molecular Formula: C₁₄H₂₇N₃O₃Si
• Molecular Weight: 313.47
• CAS Registry Number: 2224-33-1
• EC Number: 218-747-8
• SMILES: CCC(=NO[Si](C=C)(ON=C(C)CC)ON=C(C)CC)C

Properties

• Density: 0.975
• Boiling point: 115 °C (0.12 mmHg)
• Refractive index: 1.4543-1.4553

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H315-H317-H318-H319-H373
• Safety Statements: P260-P261-P264-P264+P265-P272-P280-P302+P352-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin sensitization	Skin Sens.	1B	H317
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H336
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Carcinogenicity	Carc.	1B	H350
Skin corrosion	Skin Corr.	1B	H314
Skin corrosion	Skin Corr.	1A	H314

Discovery and Applications

Vinyltris(methylethylketoxime)silane is a chemical compound that emerged in the late 20th century as a key component in the field of organosilicon chemistry. This silane derivative, characterized by its unique functional groups, has become essential in various industrial applications, particularly in the enhancement of material properties and surface treatments.

The discovery of vinyltris(methylethylketoxime)silane was motivated by the need for effective coupling agents and adhesion promoters in material science. The compound features a vinyl group, which is reactive and facilitates polymerization, along with three methylethylketoxime groups that provide functionality for cross-linking and stabilization processes. This structure makes vinyltris(methylethylketoxime)silane valuable in improving the bonding between inorganic substrates and organic polymers.

One of the primary applications of vinyltris(methylethylketoxime)silane is in the formulation of sealants and adhesives. The compound acts as a coupling agent that enhances the adhesion between the polymer matrix and the substrate, which can be metal, glass, or ceramics. This improved adhesion is critical in applications where durability and resistance to environmental factors are important, such as in automotive, construction, and electronics industries.

In addition to its use in adhesives, vinyltris(methylethylketoxime)silane is employed in the production of advanced coatings. The compound contributes to the development of coatings that exhibit excellent resistance to moisture, chemicals, and thermal stress. These properties are particularly valuable in protective coatings for industrial equipment and machinery, where resilience to harsh conditions is required.

Vinyltris(methylethylketoxime)silane also finds applications in the field of silicone rubber production. It is used as a cross-linking agent in the formulation of silicone rubbers, which are known for their high-temperature stability, flexibility, and resistance to aging. The compound’s ability to facilitate cross-linking enhances the mechanical properties and performance of silicone rubbers in various industrial applications.

The versatile applications of vinyltris(methylethylketoxime)silane underscore its importance in advancing materials technology and improving the performance of various products. However, its use must be managed with considerations for safety and environmental impact, ensuring that it contributes positively to industrial processes and product development.

References

2008. Reaction of organylalkoxysilanes with ethanolamine and disproportionation of transetherification products. *Russian Journal of General Chemistry*, 78(2).
DOI: 10.1134/s1070363208020114

2018. The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products. *Scientific Data*, 5.
DOI: 10.1038/sdata.2018.125