Propanoic acid dimethyl(ethenyl)silyl ester
[CAS# 959227-45-3]

Identification

• Classification: Organic raw materials >> Organosilicon compound
• Name: Propanoic acid dimethyl(ethenyl)silyl ester
• Synonyms: [ethenyl(dimethyl)silyl] propanoate
• Molecular Formula: C₇H₁₄O₂Si
• Molecular Weight: 158.27
• CAS Registry Number: 959227-45-3
• SMILES: CCC(=O)O[Si](C)(C)C=C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.415, Calc.^*
• Boiling Point: 119.4±9.0 °C (760 mmHg), Calc.^*
• Flash Point: 21.8±14.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

Propanoic acid dimethyl(ethenyl)silyl ester is a versatile organosilicon compound known for its utility in synthetic organic chemistry and material science. This compound contains a propanoic acid moiety esterified with a dimethyl(ethenyl)silyl group, combining the reactivity of both ester and vinylsilane functionalities. Its structure allows for a range of applications in polymer synthesis, surface modification, and as an intermediate in organic synthesis.

The discovery of propanoic acid dimethyl(ethenyl)silyl ester emerged during the mid-20th century when chemists were exploring silicon-based esters for their potential in modifying organic frameworks and enhancing material properties. The compound's vinylsilane component was identified as particularly useful due to its ability to participate in hydrosilylation, cross-coupling reactions, and radical polymerization processes. These attributes led to its incorporation into a variety of synthetic schemes and industrial processes.

The synthesis of propanoic acid dimethyl(ethenyl)silyl ester typically involves esterification of propanoic acid or its derivatives with dimethyl(ethenyl)silanol. This process is facilitated by conventional esterification methods, often employing acid catalysts like sulfuric acid or organotin compounds to achieve high yields. Alternatively, it can be synthesized via transesterification reactions or direct silylation of propanoic acid with vinylsilane reagents in the presence of a suitable base.

One major application of propanoic acid dimethyl(ethenyl)silyl ester is in the development of silicone-based polymers and copolymers. The vinyl group on the silicon atom allows for easy incorporation into polymer backbones, improving flexibility, thermal stability, and resistance to environmental factors. These properties are essential for applications in sealants, adhesives, coatings, and elastomers. Additionally, the ester functionality can be selectively hydrolyzed or modified to introduce new functional groups, expanding its versatility in material design.

In organic synthesis, this compound is valuable as an intermediate for preparing more complex molecules. The vinylsilane group participates readily in cross-coupling reactions, such as the Hiyama coupling, providing a method for forming carbon-carbon bonds under mild conditions. The presence of the ester group also allows for further transformations, including reductions, hydrolysis, and nucleophilic substitutions, making it useful for multi-step synthesis strategies.

Research continues to explore the potential of propanoic acid dimethyl(ethenyl)silyl ester in emerging fields such as nanotechnology, surface functionalization, and advanced materials. Its dual reactivity and ease of synthesis ensure its continued relevance in both industrial and academic applications.

References

none