N,N-Dimethylacrylamide (CAS No. 2680-03-7)

N,N-Dimethylacrylamide, abbreviated as DMAA, is a hydrophilic, reactive monomer essential for synthesizing water-soluble polymers and hydrogels. With the chemical formula C₅H₉NO, it is a colorless to light yellow liquid with a mild, characteristic odor. This acrylamide derivative polymerizes readily via free radical mechanisms, forming flexible, biocompatible networks ideal for biomedical and industrial applications. Its tertiary amine structure imparts pH sensitivity and cationic properties upon quaternization, enabling stimuli-responsive materials for drug delivery and tissue engineering.

CAS Number: 2680-03-7 Molecular Weight: 99.13 g/mol Synonyms: DMAA, N,N-Dimethylpropenamide, 2-Propenamide, N,N-dimethyl

Key Properties

It features precise physical and chemical traits that facilitate its polymerization and formulation versatility. The table below outlines core specifications:

Property Value/Description
Appearance Colorless to light yellow liquid
Purity ≥99.0% (GC)
Density (20°C) 0.99 g/cm³
Boiling Point 181°C
Melting Point -40°C (estimated)
Flash Point 70°C (open cup)
Refractive Index (20°C) 1.439
Solubility in Water Miscible
Viscosity (25°C) 1.2 mPa·s

These attributes confirm its low viscosity for easy handling and high water compatibility, supporting emulsion and solution polymerizations.

Applications and Uses

N,N-Dimethylacrylamide’s amide functionality and hydrophilicity drive its incorporation into advanced polymeric systems:

  • Biomedical Hydrogels: Core monomer for poly(N,N-dimethylacrylamide) (PDMA) hydrogels in tissue engineering scaffolds, providing biocompatibility, porosity, and mechanical mimicry of extracellular matrices.
  • Drug Delivery Systems: Enables pH-responsive and self-healing hydrogels for controlled release of therapeutics, enhancing targeted delivery in cancer treatments and wound healing.
  • Adhesives and Coatings: Used in water-based adhesives, pressure-sensitive tapes, and protective coatings, leveraging its adhesion promotion and film-forming capabilities.
  • Biosensors and Diagnostics: Forms ion-conductive gels and stimuli-sensitive polymers for wearable sensors and diagnostic platforms, improving sensitivity and biocompatibility.
  • Water Treatment Polymers: Copolymerized into flocculants and superabsorbents for wastewater purification and personal care products like contact lenses.

Its biodegradability and low cytotoxicity position it as a sustainable choice for eco-friendly polymer innovations.

Safety and Handling

It is toxic if swallowed or absorbed through skin, causes serious eye damage, and is flammable. It may irritate respiratory tracts and skin upon exposure. Key protocols include:

  • Storage: Keep in a cool, dry, well-ventilated area (<25°C) in airtight containers with stabilizers like hydroquinone to prevent polymerization. Avoid light, heat, and incompatibles such as strong oxidizers.
  • Handling: Wear PPE including nitrile gloves, safety goggles, and respirators. Use in a fume hood; avoid inhalation, ingestion, and skin contact. Ground equipment to prevent static ignition.
  • Environmental Impact: Toxic to aquatic organisms; contain spills with absorbents and dispose via hazardous waste incineration to minimize release.
  • Regulatory Compliance: UN 2810 (Class 6.1, PG III); aligns with GHS (H301+H311: Toxic if swallowed/in contact with skin; H318: Causes serious eye damage; H226: Flammable) and REACH/TSCA standards.

Request the Safety Data Sheet (SDS) for exposure limits and emergency measures.

Frequently Asked Questions (FAQs)

What is the primary use of N,N-Dimethylacrylamide?

It is mainly employed as a monomer in the synthesis of PDMA hydrogels for biomedical applications like tissue engineering and drug delivery.

Is N,N-Dimethylacrylamide safe for polymer synthesis?

It is toxic and flammable, requiring PPE and ventilation, but manageable in controlled lab settings; its low cytotoxicity in polymerized form supports biomedical uses.

What is the shelf life of N,N-Dimethylacrylamide?

Stored stabilized and sealed below 25°C, it remains stable for 12-18 months, with inhibitors preventing auto-polymerization—monitor for viscosity changes.

Can N,N-Dimethylacrylamide be shipped internationally?

Yes, it complies with UN 2810 for global transport, packaged in amber glass bottles or drums with stabilizers for lab to industrial quantities.

How does N,N-Dimethylacrylamide compare to acrylamide?

Unlike toxic acrylamide, N,N-Dimethylacrylamide offers safer handling, higher water solubility, and tunable pH-responsiveness for advanced hydrogel formulations.

Is N,N-Dimethylacrylamide water-soluble?

Yes, it is fully miscible with water and polar solvents, enabling homogeneous polymerization and facilitating aqueous-based processing.

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