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2-methyl-2-Propenoic acid 2-[2-(ethenyloxy)ethoxy]ethyl ester
[CAS# 76392-22-8]

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Identification
Classification Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
Name 2-methyl-2-Propenoic acid 2-[2-(ethenyloxy)ethoxy]ethyl ester
Synonyms 2-(2-ethenoxyethoxy)ethyl 2-methylprop-2-enoate
Molecular Structure CAS # 76392-22-8, 2-methyl-2-Propenoic acid 2-[2-(ethenyloxy)ethoxy]ethyl ester, 2-(2-ethenoxyethoxy)ethyl 2-methylprop-2-enoate
Molecular Formula C10H16O4
Molecular Weight 200.23
CAS Registry Number 76392-22-8
SMILES CC(=C)C(=O)OCCOCCOC=C
Properties
Solubility 5208 mg/L (25 ºC water)
Density 1.0±0.1 g/cm3, Calc.*
Index of Refraction 1.443, Calc.*
Melting point 13.01 ºC
Boiling Point 241.61 ºC, 262.6±20.0 ºC (760 mmHg), Calc.*
Flash Point 109.0±21.8 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
up Discovory and Applicatios
2-methyl-2-Propenoic acid 2-\[2-(ethenyloxy)ethoxy]ethyl ester is a chemical compound classified as an acrylate ester, featuring a 2-methyl-2-propenoic acid (commonly known as methacrylic acid) moiety esterified with a 2-\[2-(ethenyloxy)ethoxy]ethyl alcohol derivative. Structurally, it consists of a methacrylate group attached via an ester linkage to a flexible ether-containing side chain with an ethenyloxy (vinyl ether) functionality.

The synthesis of this compound generally involves the esterification of methacrylic acid with 2-\[2-(ethenyloxy)ethoxy]ethanol under acid-catalyzed conditions or via reaction with the corresponding acid chloride. The vinyl ether group within the side chain is introduced by reacting hydroxy-functionalized ethylene glycol derivatives with vinylating agents such as vinyl chloride or vinyl ethers under controlled conditions to maintain the integrity of the reactive vinyl moiety.

This compound is of significant interest in polymer and materials science due to its dual functionality: the methacrylate group can undergo free radical polymerization, while the vinyl ether group can participate in cationic polymerization or crosslinking reactions. Such bifunctional monomers enable the design of complex polymer architectures, including interpenetrating networks and copolymers with tailored physical and chemical properties.

Applications of 2-methyl-2-Propenoic acid 2-\[2-(ethenyloxy)ethoxy]ethyl ester are primarily found in the development of advanced coatings, adhesives, and photoresists. Its polymerizable groups facilitate rapid curing processes under ultraviolet (UV) or thermal initiation, making it valuable in coatings that require durability, chemical resistance, and flexibility. The presence of ether linkages in the side chain imparts hydrophilicity and flexibility to resulting polymers, improving their mechanical and surface properties.

In addition, this compound is used in the formulation of specialty polymers for biomedical applications, where controlled polymerization and biocompatibility are essential. Its versatility allows incorporation into hydrogels, drug delivery systems, and surface modification agents, leveraging the functional groups for attachment or crosslinking with biomolecules.

Characterization of this ester includes nuclear magnetic resonance (NMR) spectroscopy to confirm the presence of vinyl and methacrylate protons and carbons, verifying the ester and ether functionalities. Infrared (IR) spectroscopy identifies characteristic absorption bands for ester carbonyl groups, vinyl ether double bonds, and ether linkages. Gel permeation chromatography (GPC) is employed in polymerized samples to determine molecular weight distribution, while differential scanning calorimetry (DSC) assesses thermal properties relevant to processing.

Safety considerations for handling 2-methyl-2-Propenoic acid 2-\[2-(ethenyloxy)ethoxy]ethyl ester reflect those typical for acrylate and vinyl ether monomers. These substances may cause skin and respiratory irritation and are potentially sensitizing. Appropriate protective measures include the use of gloves, eye protection, and working in well-ventilated environments or under fume hoods to minimize exposure. Curing and polymerization processes must be carefully controlled to prevent unintended reactions or hazards.

In summary, 2-methyl-2-Propenoic acid 2-\[2-(ethenyloxy)ethoxy]ethyl ester is a bifunctional acrylate ester monomer widely utilized in advanced polymer synthesis for coatings, adhesives, and biomedical materials. Its chemical structure facilitates versatile polymerization pathways, enabling the development of materials with customized properties. Established synthetic methods, thorough analytical characterization, and standard safety protocols support its effective application in industrial and research contexts.

References

2001. Functional Methacryloyoxy Acetals: II. Electophilic Addition of Alcohols to Vinyloxyalkyl Methacrylates. Russian Journal of Organic Chemistry, 37(12).
DOI: 10.1023/a:1013905514252
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