2-Oxotetrahydrofuran-3-yl methacrylate
[CAS# 195000-66-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: 2-Oxotetrahydrofuran-3-yl methacrylate
• Synonyms: gamma-Butyrolactone methacrylate; gamma-Butyrolactone methacrylate-DVE 3-ethoxylated bisphenol A diacrylate-2-hydroxyethyl acrylate-Kayarad DPCA 60-Kayarad HX 620-neopentyl glycol dimethacrylate-NK Ester BPE 10-polypropylene glycol diacrylate-polypropylene glycol dimethacrylate-SR 214-Sartomer 350-stearyl acrylate-tricyclodecanedimethanol dimethacrylate copolymer; gamma-Butyrolactone-2-yl methacrylate
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.16
• CAS Registry Number: 195000-66-9
• SMILES: CC(=C)C(=O)OC1CCOC1=O

Properties

• Solubility: Sparingly soluble (27 g/L) (25 °C), Calc.^*
• Density: 1.17±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

2-Oxotetrahydrofuran-3-yl methacrylate, commonly abbreviated as OTMA, is a versatile compound that combines the structural features of a lactone (tetrahydrofuran-2-one) with a methacrylate group. The synthesis of OTMA was first reported in the late 20th century, when efforts were made to develop new monomers for high-performance polymers. Lactone-containing methacrylates were of particular interest to researchers because they are able to undergo polymerization while combining the desirable properties of both lactone and methacrylate functional groups. Its structure features a lactone ring that contributes to the rigidity of the molecule and the potential for ring-opening polymerization. The methacrylate group allows for free radical polymerization to form a variety of polymer structures.

OTMA can be used as a monomer for advanced polymers that exhibit unique properties such as enhanced thermal stability, mechanical strength, and solvent resistance. These polymers can be used in a variety of applications ranging from adhesives to coatings and biomedical devices. OTMA can be copolymerized with other monomers to produce copolymers that combine the properties of different monomer units. This versatility allows the polymer properties to be fine-tuned to meet specific application requirements.

OTMA-derived polymers are used to create functional materials with specific properties such as hydrophobicity, biocompatibility, or chemical resistance. These materials are used in areas such as water treatment, packaging, and medical implants. OTMA-based polymers can be used to develop surface coatings that provide protection against corrosion, wear, and environmental degradation. These coatings are used in industries such as automotive, aerospace, and electronics.

OTMA-based polymers are explored for use in drug delivery systems due to their biocompatibility and ability to degrade under physiological conditions. These polymers can encapsulate drugs and release them in a controlled manner, thereby improving the therapeutic effect. In tissue engineering, OTMA-containing polymers are used to create scaffolds that support cell growth and tissue regeneration. Their mechanical properties and biodegradability make them suitable for creating structures that can integrate with biological tissues.

OTMA is a valuable intermediate in organic synthesis. Its functional groups allow for a variety of chemical transformations that can be used to produce specialty chemicals and complex organic molecules. The reactive methacrylate groups in OTMA can act as crosslinkers in polymer networks, enhancing the mechanical properties and stability of crosslinked polymers used in coatings, adhesives, and composites.

OTMA is used to formulate UV-curable coatings that harden when exposed to ultraviolet light, with fast cure times and improved surface properties, making them ideal for electronics, automotive finishes, and protective coatings. Polymers containing OTMA are used in pressure-sensitive adhesives (PSAs) that have strong adhesion and can be removed without leaving residues for use in labels, tapes, and surface protection films.

References

2024. Organotin(IV) from Simple Complexes to Macromolecules: A Review Inspired by the Late Professor Charles Carraher. Journal of Inorganic and Organometallic Polymers and Materials, 34(7).
DOI: 10.1007/s10904-024-03019-1

2020. Nitroxide-Mediated Polymerization. Springer Series in Materials Science.
DOI: 10.1007/978-3-030-34822-9_7

2014. Effect of polymer matrix and photoacid generator on the lithographic properties of chemically amplified photoresist. Russian Microelectronics, 43(5).
DOI: 10.1134/s1063739714050023