N,N-Dimethylaminoethyl Methacrylate (DMAEMA) (CAS No. 2867-47-2)

N,N-Dimethylaminoethyl methacrylate, commonly abbreviated as DMAEMA, is a reactive functional monomer featuring a tertiary amine and methacrylate group, ideal for polymerization reactions. With the chemical formula C₈H₁₅NO₂, it appears as a colorless to light yellow liquid with a mild amine odor. This compound is a cornerstone in the synthesis of cationic polymers, enabling pH-responsive and stimuli-sensitive materials for advanced applications. Its hydrophilic nature and basicity make it indispensable in drug delivery systems, water treatment, and specialty coatings, providing tunable properties through copolymerization.

CAS Number: 2867-47-2 Molecular Weight: 157.21 g/mol Synonyms: 2-(Dimethylamino)ethyl methacrylate, 2-Dimethylaminoethyl 2-methylpropenoate, DMAEMA

Key Properties

N,N-Dimethylaminoethyl methacrylate offers well-defined physical and chemical characteristics that support its polymerization efficiency and stability. The table below outlines core specifications:

Property Value/Description
Appearance Colorless to light yellow liquid
Purity ≥99.0% (GC)
Density (25°C) 0.933 g/mL
Boiling Point 182-192°C
Melting Point -50°C
Flash Point 79°C (closed cup)
Refractive Index (20°C) 1.437
Solubility in Water Miscible (forms salts)
pH (10% aqueous solution) 7.5-8.5 (basic)

These attributes ensure compatibility with aqueous and organic media, facilitating free radical, anionic, or coordination polymerization techniques.

Applications and Uses

DMAEMA’s tertiary amine functionality imparts cationic character upon quaternization, enabling diverse applications in materials science and biomedicine:

  • Polymer Synthesis: Key monomer for producing poly(DMAEMA) and copolymers used in gene transfection vectors, enhancing cellular uptake through electrostatic interactions.
  • Drug Delivery Systems: Incorporated into pH-sensitive hydrogels and micelles for controlled release of therapeutics, responding to tumor microenvironment acidity.
  • Water Treatment: Utilized in flocculants and ion-exchange resins for wastewater purification, leveraging its ability to form polyelectrolytes.
  • Coatings and Adhesives: Enhances adhesion and antimicrobial properties in surface coatings for textiles, paper, and biomedical devices.
  • Biomedical Research: Serves as a building block for non-viral vectors in RNAi and DNA delivery, offering biocompatibility and low cytotoxicity.

Its versatility in copolymerization with acrylates or vinyl monomers supports innovation in smart materials and sustainable formulations.

Safety and Handling

N,N-Dimethylaminoethyl methacrylate is corrosive and toxic, causing severe skin burns, eye damage, and respiratory irritation. It is harmful if swallowed, inhaled, or absorbed through skin, and suspected of damaging fertility. As a flammable liquid, it poses fire risks. Essential guidelines include:

  • Storage: Keep in a cool, dry, well-ventilated area (<25°C) in tightly sealed containers under nitrogen; add stabilizers like MEHQ to prevent polymerization. Avoid acids, oxidizers, and light.
  • Handling: Wear PPE including nitrile gloves, goggles, face shield, and respirator. Use in a fume hood; avoid skin contact and inhalation. In case of exposure, rinse immediately and seek medical help.
  • Environmental Impact: Toxic to aquatic organisms; contain spills with absorbents and dispose as hazardous waste to prevent release into waterways.
  • Regulatory Compliance: UN 3265 (Class 8, PG II); complies with GHS (H302+H312: Harmful if swallowed/in contact with skin; H314: Causes severe burns; H330: Fatal if inhaled; H361: Suspected of damaging fertility).

Request the Safety Data Sheet (SDS) for comprehensive exposure controls.

Frequently Asked Questions (FAQs)

What is the primary use of N,N-Dimethylaminoethyl methacrylate?

N,N-Dimethylaminoethyl methacrylate is mainly used as a functional monomer in the synthesis of cationic polymers for gene delivery and pH-responsive drug carriers.

Is N,N-Dimethylaminoethyl methacrylate safe for laboratory handling?

It is corrosive and toxic, requiring full PPE, ventilation, and inert conditions, but manageable in controlled labs; avoid direct contact due to absorption risks.

What is the shelf life of N,N-Dimethylaminoethyl methacrylate?

Stored stabilized under nitrogen at <25°C, it remains stable for 12-18 months, with inhibitors preventing premature polymerization—test periodically.

Can N,N-Dimethylaminoethyl methacrylate be shipped internationally?

Yes, it is shipped globally under UN 3265 regulations, in amber glass bottles or drums with stabilizers, for lab to industrial volumes.

How does N,N-Dimethylaminoethyl methacrylate compare to 2-aminoethyl methacrylate?

DMAEMA’s dimethyl substitution reduces basicity and enhances hydrophobicity, improving solubility in copolymers compared to the primary amine analog.

Is N,N-Dimethylaminoethyl methacrylate water-soluble?

Yes, it is miscible with water and forms protonated salts, enabling its use in aqueous polymerizations and hydrogel formations.

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