Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride
[CAS# 6708-37-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Carboxylic anhydride
• Name: Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride
• Synonyms: 6-Endoethylene-4-cyclohexene-1,2-dicarboxylic anhydride
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18
• CAS Registry Number: 6708-37-8
• EC Number: 678-216-5
• SMILES: C1CC2C=CC1C3C2C(=O)OC3=O

Properties

• Density: 1.324
• Melting point: 146-147 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary 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.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride, often abbreviated as BCPDA, is a unique organic compound with the molecular formula C10H10O3. This compound features a bicyclic structure with an anhydride group, making it a valuable building block in organic synthesis and materials science. The structure includes a bicyclic octane ring system with two carboxylic acid groups linked through an anhydride bond.

The discovery of BCPDA is rooted in the exploration of bicyclic compounds and their utility in chemical reactions and material development. Bicyclic compounds like BCPDA are significant because their rigid, cyclic structures provide unique reactivity and stability that can be harnessed in various chemical processes. The anhydride functionality further enhances its reactivity, making BCPDA a useful compound for a range of applications.

One of the primary applications of BCPDA is in the synthesis of high-performance polymers. The compound is used as a monomer in the production of polyimides, a class of polymers known for their thermal stability, chemical resistance, and mechanical strength. Polyimides derived from BCPDA exhibit excellent properties for use in aerospace, electronics, and other demanding applications. The anhydride group in BCPDA reacts with diamines to form polyimide networks, which are employed in high-temperature and high-stress environments.

In addition to its role in polymer synthesis, BCPDA is used in the development of advanced materials with specific properties. Its rigid bicyclic structure can be incorporated into various matrices to improve mechanical strength, thermal stability, and chemical resistance. This makes BCPDA-based materials suitable for applications in coatings, composites, and other industrial products where durability and performance are crucial.

The reactivity of BCPDA also makes it a valuable intermediate in organic synthesis. The anhydride group is highly reactive towards nucleophiles, which allows for the formation of various derivatives through chemical reactions. These derivatives can be further explored for their biological activity or used as precursors in the synthesis of more complex organic molecules. For instance, BCPDA can be used to create functionalized compounds with potential applications in pharmaceuticals or agrochemicals.

Moreover, BCPDA’s unique structure provides a platform for the development of new chemical reactions and materials. Researchers continue to investigate its properties to discover new applications and optimize existing processes. The compound's ability to form highly stable and reactive intermediates is of particular interest in the design of novel chemical systems and functional materials.

In summary, Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride is a significant compound in organic chemistry and materials science. Its discovery and utilization have led to advancements in polymer synthesis, advanced materials, and organic synthesis. The unique bicyclic and anhydride structure of BCPDA provides valuable reactivity and stability, making it a key component in the development of high-performance polymers and other specialized chemical products.

References

2001. NMR Experimental Evidence of the Differentiation of Enantiotopic Directions in Cs and C2v Molecules Using Partially Oriented, Chiral Media. Journal of the American Chemical Society, 123(44).
DOI: 10.1021/ja011685l