5-Methoxynicotinaldehyde

This compound is typically obtained as a crystalline solid ranging from off-white to pale yellow. Its molecular formula is C7H7NO2, corresponding to a molecular weight of 137.14. The melting point generally falls within the range of 72–76 ℃. The calculated density is approximately 1.19 g/cm³ under ambient conditions. It is readily soluble in common organic solvents including methanol, ethanol, dichloromethane, and ethyl acetate, moderately soluble in dimethyl sulfoxide, and only sparingly soluble in water and non-polar solvents such as hexane. The molecule features a pyridine ring substituted with a methoxy group at the 5-position and an aldehyde function at the 3-position. The aldehyde is susceptible to oxidation and condensation reactions, while the methoxy group contributes electron density through resonance. Storage in a tightly sealed container under inert atmosphere, protected from light and moisture, is recommended. Contact with strong oxidizing agents and strong bases should be avoided.

5-Methoxynicotinaldehyde is a disubstituted pyridine derivative that combines an electron-donating methoxy group and an electrophilic aldehyde moiety on the heteroaromatic ring. The pyridine core, with its inherently electron-withdrawing nitrogen atom, provides a moderately electron-deficient platform capable of engaging in π-stacking and hydrogen bonding interactions. The methoxy substituent at the 5-position donates electron density through resonance, partially counterbalancing the ring's electron deficiency and influencing the reactivity of the aldehyde at the 3-position. The formyl group serves as a versatile electrophilic handle for further functionalization through condensation, reduction, or oxidation reactions. This compact, bifunctional structure makes the molecule a valuable intermediate for constructing more complex pyridine-based compounds with potential applications in medicinal chemistry and materials science.

In drug discovery, this methoxypyridine aldehyde is employed as a building block for synthesizing compounds with potential activity against cancer, inflammation, and infectious diseases. The aldehyde group enables reductive amination to introduce basic amine side chains or condensation with hydrazines to form hydrazone pharmacophores. The methoxy substituent can influence metabolic stability and binding affinity through electronic effects, while the pyridine core provides hydrogen-bonding capacity essential for interactions with enzyme active sites.

The compound serves as a precursor for constructing fused heterocycles such as pyrido[2,3-d]pyrimidines, pyrazolo[3,4-b]pyridines, and imidazo[1,2-a]pyridines through cyclocondensation reactions with appropriate dinucleophiles. These ring systems are extensively investigated for their pharmacological properties, with the rigid pyridine core providing conformational constraint beneficial for target recognition and selectivity.

The pyridine nitrogen can coordinate to transition metals, forming complexes with well-defined geometries. The aldehyde group can be converted to Schiff bases or other donor functionalities, creating polydentate ligand systems. Metal complexes derived from this scaffold are studied for their catalytic activity in oxidation and cross-coupling reactions, as well as for their potential as luminescent materials and models for metalloenzyme active sites.

As a versatile building block, 5-methoxynicotinaldehyde participates in diverse transformations including Wittig olefinations, Grignard additions, and palladium-catalyzed cross-coupling reactions after appropriate functional group interconversion. The aldehyde can be oxidized to the carboxylic acid for amide coupling or reduced to the alcohol for ether formation. Its utility extends to the synthesis of natural product analogs and functional materials where the pyridine ring imparts desirable electronic and hydrogen-bonding properties.

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