5-Methacryloxy-6-hydroxynorbornane-2-carboxylic-6-lactone
[CAS# 254900-07-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 5-Methacryloxy-6-hydroxynorbornane-2-carboxylic-6-lactone
• Synonyms: 4-Oxa-5-oxotricyclo[4.2.1.0(3,7)]nonan-2-yl methacrylate
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24
• CAS Registry Number: 254900-07-7
• EC Number: 835-616-6
• SMILES: CC(=C)C(=O)OC1C2CC3C1OC(=O)C3C2

Properties

• Solubility: Very slightly soluble (0.42 g/L) (25 °C), Calc.^*
• Density: 1.26±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: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

5-Methacryloyloxy-6-hydroxynorbornane-2-carboxylic acid-6-lactone, also known as "norbornyl methacrylate lactone" or NBML, is a special chemical compound. Chemically, NBML is a bicyclic lactone with the molecular formula C₁₅H₁₈O₅. It has a norbornane backbone that is functionalized with both hydroxyl and methacrylate moieties. This unique structure gives NBML dual reactivity, being able to participate in polymerization reactions via the methacrylate group and undergo ring-opening reactions due to its lactone functionality.

The discovery of NBML can be traced back to research aimed at developing new monomers for polymerization processes. Its synthesis involves the reaction of methacrylic acid with 5-hydroxy-6-norbornene-2-carboxylic acid, followed by lactonization to form a cyclic lactone structure. This synthetic route not only ensures the production of a stable reactive monomer, but also facilitates its incorporation into a polymer matrix with a controlled molecular architecture.

In polymer chemistry, NBML is a versatile monomer used to synthesize cross-linked networks and copolymers with desirable mechanical and thermal properties. Its ability to polymerize via free radical polymerization techniques, such as UV-initiated polymerization, enables the fabrication of high-performance materials for coatings, adhesives, and biomedical devices. The presence of hydroxyl groups in NBML also facilitates post-polymerization modifications, allowing functionalization and surface grafting to tailor material properties to specific applications.

In addition to its role in materials science, NBML can be used in biomedical engineering and drug delivery systems. The hydroxyl groups can be used for conjugation to biomolecules or therapeutic agents, while the methacrylate groups can be incorporated into biocompatible polymers for controlled release formulations. This versatility has led to the study of NBML-based hydrogels and tissue engineering scaffolds, which offer significant advantages in terms of biocompatibility and tunable properties.

The discovery and development of NBML highlights the intersection of synthetic chemistry and materials science in creating functional materials with tailored properties. Its unique structure and dual reactivity provide researchers and engineers with a versatile platform for designing advanced materials that address specific technological and biomedical challenges.

References

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