Vinyl Azlactone, also known as vinyl dimethyl azlactone (VDM), is a reactive monomer containing a polymerizable vinyl group and an electrophilic azlactone ring. This dual functionality supports the preparation of polymers, coatings, and surfaces that can undergo subsequent reaction with nucleophiles such as primary amines and thiols.
Synonyms: Vinyl Dimethyl Azlactone; VDM.
The vinyl group enables incorporation into compatible polymerization systems, while the azlactone ring provides a reactive site for post-polymerization functionalization. This makes Vinyl Azlactone useful for preparing reactive polymers and surfaces that can be modified with amine- or thiol-containing compounds.
Product 21329 has a minimum chemical purity of 95%. Vinyl Azlactone hydrolyzes to N-acryloyl-2-methylalanine, so moisture exposure and reaction conditions should be carefully controlled during storage and use.
Key Properties
- Reactive vinyl azlactone monomer
- Minimum chemical purity: 95%
- CAS number 29513-26-6
- Molecular formula: C7H9NO2
- Molecular weight: 139.2 g/mol
- Light yellow liquid
- Boiling point: 52°C at 9 mm Hg
- Refractive index: 1.4575
- Melting point: 6°C
- Product number 21329
Applications
Reactive Polymer Synthesis
Vinyl Azlactone may be incorporated into compatible polymerization systems to prepare polymers containing reactive azlactone functionality.
Post-Polymerization Functionalization
Azlactone-functional polymers can react with suitable nucleophiles, including primary amines and thiols, enabling subsequent modification of the polymer structure.
Reactive Coatings & Adhesives
May be evaluated in coatings and adhesive formulations where covalent reaction with compatible amine- or thiol-functional components is required.
Surface Functionalization
Vinyl Azlactone can be used in materials research to prepare reactive surfaces for subsequent coupling with amine-containing molecules.
Bioconjugation & Immobilization Research
Azlactone-functional materials may be used in research workflows involving the immobilization or coupling of proteins, peptides, and other molecules containing accessible nucleophilic groups.
Compatibility & Reaction Considerations
- Suitable for evaluation in compatible vinyl polymerization systems
- Azlactone functionality reacts with nucleophiles such as primary amines and thiols
- Reaction performance depends on solvent, concentration, temperature, and accessibility of the nucleophilic group
- Exposure to moisture may promote hydrolysis of the azlactone ring
The appropriate monomer concentration, polymerization conditions, and functionalization protocol depend on the selected comonomers, initiator system, solvent, and target material properties.
Application Tips
- Use controlled, small-scale trials to establish suitable polymerization conditions
- Limit unnecessary exposure to moisture during storage and handling
- Evaluate compatibility with comonomers, initiators, solvents, and other formulation components
- Confirm azlactone incorporation and subsequent functionalization using appropriate analytical methods
Handling & Storage
- Store at -20°C
- Keep the container tightly closed in a cool, well-ventilated location
- Keep away from heat, sparks, open flames, and other ignition sources
- Wear protective gloves, protective clothing, and safety glasses
- Use in a fume hood or with adequate laboratory ventilation
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FAQ
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1. What is Vinyl Azlactone?
Vinyl Azlactone is a reactive monomer containing a polymerizable vinyl group and an electrophilic azlactone ring. It is also known as vinyl dimethyl azlactone or VDM.
2. What is the structure of Vinyl Azlactone?
Vinyl Azlactone contains a vinyl group that supports polymerization and an azlactone ring that provides a reactive site for subsequent chemical functionalization.
3. What is Vinyl Azlactone used for?
It is used in reactive polymer synthesis, post-polymerization functionalization, surface modification, coatings, adhesives, and research involving the coupling or immobilization of amine-containing molecules.
4. What compounds react with the azlactone group?
The electrophilic azlactone ring can react with suitable nucleophiles, including primary amines and thiols. Reaction conditions should be optimized for the selected polymer, surface, or target molecule.
5. Does Vinyl Azlactone hydrolyze?
Yes. Vinyl Azlactone hydrolyzes to N-acryloyl-2-methylalanine. Limiting moisture exposure can help preserve azlactone functionality before polymerization or coupling.
6. How should Vinyl Azlactone be stored?
Store product 21329 at -20°C with the container tightly closed. Keep it away from heat, sparks, open flames, and other ignition sources.
Safety & Documentation
Vinyl Azlactone is a flammable liquid and vapor that causes skin and eye irritation. Handle it with protective gloves, protective clothing, and safety glasses in a fume hood or well-ventilated workspace. Keep away from ignition sources and review the Safety Data Sheet and lot-specific Certificate of Analysis before use.
