Isobornyl methacrylate
[CAS# 7534-94-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Other ester compounds
• Name: Isobornyl methacrylate
• Synonyms: Methacrylic acid isobornyl ester; (1,7,7-Trimethyltricyclo[2.2.1]hepten-2-yl)-2-methyl-2-propenoate
• Molecular Formula: C₁₄H₂₂O₂
• Molecular Weight: 222.32
• CAS Registry Number: 7534-94-3
• EC Number: 231-403-1
• SMILES: CC(=C)C(=O)O[C@@H]1C[C@H]2CC[C@@]1(C2(C)C)C

Properties

• Water solubility: negligible
• Density: 1.0±0.1 g/cm³, Calc.^*, 0.98 g/cm³
• Index of Refraction: 1.488, Calc.^*
• Melting point: -60 °C
• Boiling Point: 263.1±9.0 °C (760 mmHg), Calc.^*, 245 °C
• Flash Point: 104.0±16.1 °C, Calc.^*, 101 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H411-H412
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Isobornyl methacrylate is a chemical compound with the molecular formula C₁₁H₁₆O₂, known for its distinctive bicyclic structure and versatile applications. The compound belongs to the class of methacrylate esters, which are widely used in polymer chemistry and material science. Its discovery and subsequent development have significantly impacted various industries, particularly in the production of advanced polymers and coatings.

The synthesis of isobornyl methacrylate involves the esterification of methacrylic acid with isobornol, a bicyclic alcohol derived from pinene. The reaction is typically carried out under acidic conditions to yield the ester product. The resulting compound features a unique bicyclic structure derived from the isobornol moiety, which contributes to its distinctive chemical and physical properties.

Isobornyl methacrylate has found extensive use in the field of polymer chemistry due to its ability to impart specific characteristics to polymers. One of its primary applications is in the production of high-performance coatings and adhesives. The compound's methacrylate group enables it to participate in free radical polymerization, resulting in polymers with excellent mechanical properties, chemical resistance, and adhesion. These properties make isobornyl methacrylate-based polymers suitable for demanding applications such as automotive coatings, aerospace materials, and industrial adhesives.

In addition to coatings and adhesives, isobornyl methacrylate is utilized in the manufacturing of optical materials. The compound's unique structural features contribute to the creation of polymers with high optical clarity and low dispersion. This makes it valuable in the production of optical lenses, light guides, and other optical components where precise optical properties are required.

The compound also plays a role in the field of dental materials. Its incorporation into dental resins enhances the mechanical strength and durability of dental restorations. The ability of isobornyl methacrylate to form strong, durable polymers is beneficial for applications such as dental fillings, crowns, and bridges.

Furthermore, isobornyl methacrylate is employed in the formulation of specialty polymers used in the electronics industry. Its inclusion in formulations for electronic encapsulants and coatings helps to protect sensitive electronic components from environmental factors such as moisture and chemicals.

Overall, isobornyl methacrylate is a valuable chemical compound with diverse applications across various industries. Its role in enhancing the performance and durability of materials underscores its importance in advancing technologies related to coatings, adhesives, optical materials, and dental products.

References

1981 Determination of partition coefficients of acrylates, methacrylates, and vinyl monomers using high performance liquid chromatography (HPLC). Journal of Biomedical Materials Research, 15(6).
DOI: 10.1002/jbm.820150603