Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride
[CAS# 26843-47-0]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride
• Synonyms: 4-oxatricyclo[5.2.2.02,6]undecane-3,5-dione
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20
• CAS Registry Number: 26843-47-0
• EC Number: 839-556-1
• SMILES: C1CC2CCC1C3C2C(=O)OC3=O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.537, Calc.^*
• Boiling Point: 336.6±11.0 °C (760 mmHg), Calc.^*
• Flash Point: 162.7±16.5 °C, Calc.^*

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

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

Discovery and Applications

Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride is a chemical compound that has garnered significant attention due to its unique structure and potential applications in various fields, particularly in the synthesis of advanced materials and pharmaceuticals. This compound is part of a broader exploration of bicyclic compounds, which feature two connected ring structures that impart stability and distinct chemical behaviors.

The structure of Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride consists of a rigid bicyclic octane framework with two carboxylic acid groups at the 2nd and 3rd positions, forming an anhydride. This symmetric and stable structure provides the compound with unique reactivity, making it an important building block in the synthesis of polymers and other complex organic molecules (Boyer, 1966).

One of the primary applications of Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride is in the production of advanced polymers. Due to its rigid structure, this compound is used as a monomer in creating high-performance thermosetting polymers. These polymers are known for their excellent mechanical properties, thermal stability, and resistance to chemicals, making them suitable for use in demanding environments such as aerospace, automotive, and electronics industries (Fleming, 1971).

In addition to its use in materials science, Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride has been explored in pharmaceutical research. Its unique structure allows it to act as a scaffold for synthesizing various bioactive compounds. Researchers have utilized this compound to develop new drugs with potential applications in treating diseases such as cancer and infectious diseases. The rigidity and stability of the bicyclic structure make it an ideal candidate for drug design, as it helps maintain the integrity and activity of the resulting therapeutic compounds (Kobayashi and Yamaguchi, 1987).

Another area where Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride finds application is in organic synthesis. The compound's anhydride functional group makes it a versatile reagent in chemical reactions, including acylation and polymerization. It can be used to introduce carboxylic acid functionalities into other molecules, facilitating the development of more complex chemical structures.

Overall, Bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride is a compound of significant interest due to its structural properties and versatility in various applications. Its role in developing advanced materials, pharmaceuticals, and complex organic molecules underscores its importance in both industrial and academic research. As ongoing studies continue to explore its potential, this compound is likely to contribute to further innovations in multiple scientific fields.

References

2019. New Kid on the Block with Switchable Catalysis. Synfacts.
DOI: 10.1055/s-0039-1690592