2,2'-Bipyridyl-5,5'-dialdehyde: properties, synthesis and safety

General Description

2,2'-Bipyridyl-5,5'-dialdehyde is a yellow solid compound with moderate hydrophobicity and specific properties such as hydrogen bond acceptor counts and rotatable bond counts. This versatile compound finds applications in coordination chemistry, catalysis, and materials science due to its ability to act as a ligand and form stable complexes, enhance reactivity and selectivity, and serve as a building block for COFs. However, 2,2'-Bipyridyl-5,5'-dialdehyde is classified as an irritant and can be harmful if swallowed, necessitating proper handling and storage protocols. Overall, the unique properties and potential applications of 2,2'-Bipyridyl-5,5'-dialdehyde make it a valuable compound in various scientific and technological fields.

Figure 1. 2,2'-Bipyridyl-5,5'-dialdehyde

Properties

2,2'-Bipyridyl-5,5'-dialdehyde, with the chemical formula C12H8N2O2 and a molecular weight of 212.20 g/mol, is a yellow solid compound that finds applications in various fields. It exhibits moderate hydrophobicity, as indicated by its low XLogP3-AA value of 0.4. The molecular structure of this compound can be represented in both 2D and 3D conformations. With four hydrogen bond acceptor counts and three rotatable bond counts, 2,2'-Bipyridyl-5,5'-dialdehyde possesses specific characteristics that contribute to its interactions with other molecules. Its topological polar surface area of 59.9Ų suggests its potential involvement in molecular interactions. Furthermore, the compound's complexity value of 231 provides insights into its structural intricacies. These properties collectively make 2,2'-Bipyridyl-5,5'-dialdehyde a compound of interest in various applications where its hydrophobic nature, hydrogen bond acceptor capabilities, and structural complexity can potentially play a role. It is important to note that further research and analysis may be necessary to explore the full extent of its properties and applications in specific scientific and industrial contexts. ¹

Applications

2,2'-Bipyridyl-5,5'-dialdehyde is a versatile compound with various applications in different fields. Its unique chemical structure and properties make it suitable for several purposes. One significant application of 2,2'-Bipyridyl-5,5'-dialdehyde is in coordination chemistry and catalysis. It can act as a ligand, forming coordination complexes with transition metals. These complexes exhibit interesting catalytic properties and are used in various organic transformations, such as cross-coupling reactions, C-H activation, and asymmetric catalysis. The presence of the bipyridyl moiety in BPDA enables it to form stable complexes, enhancing the reactivity and selectivity of these catalytic processes. Another important application of 2,2'-Bipyridyl-5,5'-dialdehyde lies in materials science, specifically in the synthesis of functional polymers and covalent organic frameworks (COFs). BPDA can serve as a building block in the construction of COFs, which are porous materials with high surface areas and tunable pore sizes. These COFs have applications in gas storage, separation, and sensing. By incorporating BPDA into the COF structure, the resulting material can possess enhanced chemical stability and improved performance in specific applications. In summary, 2,2'-Bipyridyl-5,5'-dialdehyde finds applications in coordination chemistry, catalysis and materials science. Its versatility and unique properties make it a valuable compound in these fields, contributing to advancements in various scientific and technological areas. ^2,3

Safety

In terms of safety, it is important to handle 2,2'-Bipyridyl-5,5'-dialdehyde with caution due to its classification as an irritant. According to the Globally Harmonized System (GHS), this compound carries a hazard statement of H302, indicating that it can be harmful if swallowed. It is crucial to take precautionary measures when working with this compound to minimize potential health risks. To ensure safe handling, it is recommended to avoid ingestion of 2,2'-Bipyridyl-5,5'-dialdehyde. Proper laboratory safety protocols should be followed, including the use of appropriate personal protective equipment such as gloves, goggles, and lab coats. It is also advisable to work in a well-ventilated area or under a fume hood to prevent inhalation of any vapors or aerosols. When storing this compound, it is important to keep it in a tightly sealed container away from incompatible substances. It should be stored in a cool, dry place, and away from direct sunlight or sources of heat. Additionally, it is advisable to label the container properly with the name of the compound and any relevant hazard symbols or warnings. By acknowledging and adhering to these safety guidelines and warnings associated with 2,2'-Bipyridyl-5,5'-dialdehyde, one can minimize the potential risks and ensure the safe handling and storage of this chemical compound. ⁴

Reference

1. PubChem. COMPOUND SUMMARY: [2,2'-Bipyridine]-5,5'-dicarbaldehyde. National Center for Biotechnology Information, PubChem CID: 15547968.

2. A Covalent Organic Framework Material Containing Oxadiazole Linker. ational Center for Biotechnology Information, 2023, PubChem Patent Summary for CN-114085388-B.

3. Heteroporous covalent organic framework sponge composite material and preparation method and application thereof. National Center for Biotechnology Information, 2023, PubChem Patent Summary for CN-115228449-A.

4. 5,5'-Bis(formyl)-2-2'-bipyridine. European Chemicals Agency, EC / List no. 635-105-6.