2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester
[CAS# 86273-46-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester
• Synonyms: 2-(2-ethenoxyethoxy)ethyl prop-2-enoate
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.21
• CAS Registry Number: 86273-46-3
• EC Number: 451-690-9
• SMILES: C=CC(=O)OCCOCCOC=C

Properties

• Solubility: 1.797e+004 mg/L (25 °C water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.441, Calc.^*
• Melting point: 10.48 °C
• Boiling Point: 228.34 °C, 244.5±20.0 °C (760 mmHg), Calc.^*
• Flash Point: 100.2±21.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H317-H412
• Safety Statements: P261-P264-P270-P272-P273-P280-P301+P317-P302+P352-P321-P330-P333+P313-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester is a chemical compound belonging to the class of acrylate esters. It features a 2-propenoic acid moiety (commonly known as acrylic acid) esterified with a 2-[2-(ethenyloxy)ethoxy]ethyl alcohol derivative. Structurally, this compound consists of an acrylic acid group linked via an ester bond to a side chain containing ethoxy and vinyl ether functional groups, which impart distinct polymerization characteristics.

The synthesis of this compound typically involves the esterification of acrylic acid with 2-[2-(ethenyloxy)ethoxy]ethanol under acid-catalyzed conditions or through the reaction of acrylic acid derivatives such as acryloyl chloride with the corresponding alcohol. The presence of the vinyl ether (ethenyloxy) group in the side chain is introduced through the reaction of ethylene glycol derivatives with vinylating agents, preserving the reactive vinyl functionality.

This compound is valued in polymer chemistry for its bifunctional nature, combining the well-known free radical polymerizability of the acrylic ester group with the cationic polymerization capability of the vinyl ether moiety. Such dual polymerizable functionality allows the design of advanced polymer networks with tailored physical, chemical, and mechanical properties. These properties enable applications in UV-curable coatings, adhesives, inks, and other specialty materials requiring rapid curing and enhanced performance.

In addition, 2-propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester is used in biomedical materials development due to its ability to form hydrophilic polymers with flexibility and biocompatibility. The ether linkages in the side chain contribute to polymer hydrophilicity, which is beneficial in hydrogel formation, drug delivery systems, and surface modifications.

Characterization of this compound involves nuclear magnetic resonance (NMR) spectroscopy to confirm the presence of both acrylic and vinyl ether protons and carbons, ensuring correct structural integrity. Infrared (IR) spectroscopy identifies characteristic absorption bands corresponding to ester carbonyl, vinyl ether double bonds, and ether linkages. Gel permeation chromatography (GPC) is employed for molecular weight analysis of polymers derived from this monomer, while differential scanning calorimetry (DSC) assesses thermal properties relevant to processing and end-use.

Safety considerations for handling 2-propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester align with general precautions for acrylate and vinyl ether monomers. These substances may cause skin and respiratory irritation and have sensitizing potential. It is recommended to use gloves, eye protection, and adequate ventilation or fume extraction to minimize exposure. Controlled curing conditions are essential to prevent unintended polymerization or hazardous reactions.

In summary, 2-propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester is a bifunctional acrylate ester monomer combining free radical and cationic polymerizable groups. It is widely employed in advanced polymer synthesis for coatings, adhesives, and biomedical materials due to its versatile polymerization behavior and favorable properties. Established synthetic methods, thorough analytical characterization, and adherence to safety protocols support its effective application in industrial and research settings.

References

2014. Synthesis and properties of poly(2-adamantyl vinyl ether)-based optical plastics. Polymer Bulletin, 71(6).
DOI: 10.1007/s00289-014-1130-5

2013. ToF-S-SIMS molecular 3D analysis of micro-objects as an alternative to ion beam erosion at large depth: application to single inkjet dots. Analytical and Bioanalytical Chemistry, 405(12).
DOI: 10.1007/s00216-012-6647-6

Compound: 2-(2-Vinyloxyethoxy)ethyl acrylate homopolymer.