pyridine-2,6-dicarboxylic acid CAS 499-83-2, pyridine-2,6-dicarboxylic acid, CAS 499-83-2
Among numerous organic ligands, 2, 6-pyridine dicarboxylic acid derivatives have demonstrated particularly outstanding sensitization and luminescence capabilities.
499-83-2
C7H5NO4
167.12
207-894-3
Chemical Name | Pyridine-2,6-dicarboxylic acid |
Other Name | 2,6-Pyridinedicarboxylic acid; Dipicolinic acid |
CAS | 499-83-2 |
EINECS | 207-894-3 |
Type | Pharmaceutical intermediates; Pharmaceutical raw materials; Organic raw materials |
Molecular Formula | C7H5NO4 |
Molecular Weight | 167.12 |
Melting point | 248-250 °C (dec.)(lit.) |
Boiling point | 295.67°C (rough estimate) |
density | 1.5216 (rough estimate) |
vapor pressure | <0.01 hPa (20 °C) |
refractive index | 1.6280 (estimate) |
Fp | 188 °C |
storage temp. | Store below +30°C. |
solubility | H2O: 1%, clear |
pka | 2.16(at 25℃) |
form | Crystalline Powder |
color | White |
PH | 2.0 (5g/l, H2O, 20℃) |
Water Solubility | 5 g/L (20 ºC) |
Among numerous organic ligands, 2, 6-pyridine dicarboxylic acid derivatives have demonstrated particularly outstanding sensitization and luminescence capabilities. Compared with salicylic acid derivatives, it can absorb and transfer energy more effectively in certain specific luminescent systems, enabling the luminescent substances that cooperate with it to emit brighter and more stable light. Compared with o-phenanthroline ligands, 2, 6-pyridine dicarboxylic acid derivatives have unique advantages in molecular structure. Their specific functional group combinations can better coordinate with rare earth ions, etc., thereby enhancing the effect of sensitization and luminescence. Even compared with common organic ligands such as B-diketone compounds, 2, 6-pyridine dicarboxylic acid derivatives perform better in sensitization luminescence and can achieve efficient photosensitization over a wider wavelength range.
Meanwhile, some rare earth complexes of 2, 6-pyridine dicarboxylic acid exhibit the characteristics of chiral molecules. The uniqueness of this chiral molecule lies in that when its circularly polarized luminescence spectrum is measured, more information can be obtained compared to ordinary non-chiral molecules. This additional information is of extremely significant importance for in-depth research on the microstructure, optical activity, and interactions with other substances of molecules, providing more abundant and detailed data support for scientific research in related fields.
2, 6-pyridine dicarboxylic acid has important applications in the field of organic synthesis and can be used to prepare 2, 6-pyridine dimethanol. In the complex system of organic synthesis, 2, 6-disubstituted pyridine is a kind of extremely crucial intermediate, and 2, 6-pyridine-dimethanol, with its unique chemical properties, has a wide range of application prospects. Hydroxyl, as a common and important functional group, has high activity and variability in organic chemical reactions. It can be transformed into many other groups through a series of carefully designed chemical reactions. For example, it can be converted into amino groups, thereby changing the chemical properties of molecules such as basicity and nucleophilicity. Or it can be converted into an aldehyde group, providing active sites for further REDOX reactions or other organic synthesis steps; It can also be converted into halogenated hydrocarbons, expanding the application scope of the molecule in nucleophilic substitution reactions and other processes.
Due to the special molecular structure feature that 2, 6-pyridine dicarboxylic acid has substituent groups at the 2nd and 6th positions, it is capable of generating macrocyclic molecules. This large-ring molecule has a unique cyclic structure, which endows it with many special physical and chemical properties, such as high stability, selectivity, and unique optical and electrical performance. Therefore, it has high research value in scientific research and practical applications and is widely used in the synthesis of various organic compounds, materials, and bioactive molecules with specific functions.
Pyridin-2, 6-dicarboxylic acid, as an important intermediate in drug synthesis, plays an indispensable role in the field of pharmaceutical and chemical engineering, and its applications are very extensive. It participates in the synthesis process of numerous drug molecules and provides a key structural unit for the research and development of new drugs. It is worth noting that pyridine-2, 6-dicarboxylic acid exists naturally in bacterial spores. However, its content in nature is extremely low and far from meeting the demands of large-scale industrial production and scientific research. Moreover, extracting this substance from bacterial spores faces many technical challenges, such as a complex extraction process, high cost, and low yield, which makes it unsuitable for direct natural extraction in industrial production or practical applications.
Looking back at history, in 1935, Alvin W. Singer and S. M. McElvain from the University of Wisconsin conducted a pioneering study. They used a mixture of potassium permanganate and water as the solvent. The oxidation reaction of 2, 6-lutidine was carried out to prepare pyridine-2, 6-dicarboxylic acid, and finally a yield of 64% was achieved. This research achievement provides an important basis and reference for the subsequent exploration of the synthetic method of this substance. In today's industrial production processes, the method of oxidizing 2-6-lutidine is usually adopted to prepare pyridine-2, 6-dicarboxylic acid. However, with the continuous development and improvement of technology, optimizations and innovations have been made in aspects such as reaction conditions, catalyst selection, and post-treatment processes. To enhance production efficiency, reduce costs and minimize the impact on the environment.
In the vast field of organic chemistry, pyridine-2, 6-dicarboxylic acid, as a unique pyridine dicarboxylic acid, has its specific structure and properties. This compound precisely has two carboxyl groups distributed at the 2nd and 6th positions of its molecular structure. This special structure endows it with many unique chemical properties and functions.
From the perspective of biological metabolism, pyridine-2, 6-dicarboxylic acid plays an important role in bacterial metabolites. In the complex process of bacterial metabolism, it participates in a series of subtle biochemical reactions and has a non-negligible influence on the growth, reproduction and metabolic regulation of bacteria. Meanwhile, it is also the conjugate acid of dipyridine ester (1 -), and this relationship further enriches its chemical properties and reaction characteristics within the realm of acid-base chemistry.
In the field of microbiology research, dipyridinic acid has demonstrated some interesting phenomena and mechanisms of action. For instance, through autoclaving, bispyridinic acid can be released from the spores of Thermophilus stearothermophilus. This process is not a simple physical release but involves a series of complex biochemical changes. When dipyridinic acid is released, it induces the aggregation of chitosan-stable gold nanoparticles. This aggregation behavior directly leads to a significant change in the solution color, gradually transforming from the original red to blue. This color change provides a visual basis and clue for related research.
In terms of organic synthesis, using 2, 6-pyridine dicarboxylic acid as the basic raw material, 2, 6-pyridine dicarboxylic acid derivatives can be ingeniously prepared. 2, 6-pyridine dicarboxylic acid itself has a definite molecular formula C7H5NO4, and its molecular weight has been precisely determined to be 167.12. From the perspective of the appearance and form of the substance, it presents a needle-like crystal structure. This crystal structure not only reflects the internal molecular arrangement rules but also influences its physical and chemical properties to a certain extent. Moreover, it has poor solubility in ethanol. The characteristic of being insoluble in ethanol gives it unique advantages in specific operations such as separation and purification. In addition, it can also serve as a competitive inhibitor of glutamate dehydrogenase in bovine liver and has potential application value in the research of enzyme-catalyzed reactions.
In the field of coordination chemistry, pyridine-2, 6-dicarboxylic acid has important applications. It is often used to prepare dipyridine-coordinated lanthanide and transition metal complexes. During the formation process of these complexes, pyridine-2, 6-dicarboxylic acid, with its unique structure and chemical properties, can effectively coordinate and combine with lanthanide and transition metal ions, thereby forming complexes with specific properties and functions. Meanwhile, due to the presence of active groups such as carboxyl groups in its molecular structure, it can serve as a chelating agent for various metal ions including chromium, zinc, manganese, copper, iron and molybdenum. Through chelation, it forms stable cyclic structures with metal ions. This chelation has wide applications in the separation and detection of metal ions as well as the preparation of related materials.
It is worth mentioning that the calcium-dipyridine acid complex of pyridine-2, 6-dicarboxylic acid has an outstanding ability to protect deoxyribonucleic acid (DNA) from thermal denaturation. In the research and application of DNA, thermal denaturation is a problem that requires key attention, and this complex can effectively improve the stability of DNA, providing strong support for the development and application of DNA-related technologies. Moreover, in terms of the evaluation of sterilization effects, it is also an important landmark substance.
From the perspective of microbial metabolism, a thorough exploration reveals that dipyridic acid is an amphoteric metabolite produced by many bacteria and fungi. Before its identity as a microbial metabolite was clearly defined in the early days, pyridine dicarboxylic acid had already been recognized as a chelating agent for many metal ions, and its significance in the chemistry of metal ion coordination was self-evident. The wide distribution of pyridine dicarboxylic acid in microorganisms makes it an important criterion for repeated discovery. It plays a significant role in the classification and identification of microorganisms, ecological research, and the development of related biotechnologies. Especially in the endospores of Bacillus, pyridine dicarboxylic acid can reach a high concentration (about 10% w/w). The accumulation of this high concentration makes a significant contribution to the heat resistance of Bacillus, and in the laboratory environment, it is widely used as an indicator of sterilization effect, providing a reliable basis for the detection and control of aseptic environments.