DL-Bornane-2,3-dione
[CAS# 10373-78-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Bicyclic compound
• Name: DL-Bornane-2,3-dione
• Synonyms: 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• CAS Registry Number: 10373-78-1
• EC Number: 233-814-1
• SMILES: CC1(C2CCC1(C(=O)C2=O)C)C

Properties

• Melting point: 140-142 °C

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

DL-Bornane-2,3-dione, commonly known as camphorquinone, is a bicyclic diketone with the chemical formula C₁₀H₁₄O₂. This compound has garnered significant attention due to its application as a photoinitiator in the polymerization of dental resins and other light-cured materials. Its discovery and subsequent utilization have played a crucial role in the advancement of dental restoration technologies, offering improved performance and durability in dental composites.

Camphorquinone was first isolated in the early 20th century during studies of natural products derived from camphor. The compound is synthesized through the oxidation of camphor, a naturally occurring terpene, using chemical oxidizing agents such as nitric acid or potassium permanganate. The resulting diketone is a yellow crystalline solid, characterized by its ability to absorb light in the blue region of the visible spectrum, making it highly effective as a photoinitiator.

The primary application of DL-Bornane-2,3-dione lies in its use as a photoinitiator for the polymerization of methacrylate-based dental resins. When exposed to blue light, typically at wavelengths around 468 nm, camphorquinone undergoes a photochemical reaction that generates free radicals. These radicals initiate the polymerization of the resin monomers, leading to the formation of a solid polymer matrix. This light-activated process allows for the precise control of curing time and depth, enabling dental professionals to achieve optimal results in restorative procedures such as fillings, crowns, and veneers.

In addition to its role in dental materials, DL-Bornane-2,3-dione is also used in the formulation of light-cured adhesives and coatings. Its photoinitiating properties make it suitable for applications requiring rapid and efficient curing under controlled light exposure. The use of camphorquinone in these products ensures strong adhesion and resistance to wear, making it a valuable component in various industrial and consumer applications.

The effectiveness of camphorquinone as a photoinitiator has also led to its exploration in other fields, including 3D printing and photopolymerization-based manufacturing processes. Its ability to initiate polymerization under visible light conditions makes it compatible with various photopolymers, allowing for the development of high-precision, durable materials in advanced manufacturing technologies.

DL-Bornane-2,3-dione continues to be an essential compound in the field of photopolymerization, driving innovations in dental care and other industries reliant on light-cured materials. Its discovery and application have significantly enhanced the performance and reliability of materials used in a wide range of applications, solidifying its importance in modern material science.

References

1901. Kampfer und Terpene. Die Arzneimittel-Synthese auf Grundlage der Beziehungen zwischen chemischem Aufbau und Wirkung.
DOI: 10.1007/978-3-662-37007-0_12