4-Pyridinecarboxaldehyde-Application

4-Pyridinecarboxaldehyde(4PCA) is a slightly yellow oily liquid. Its boiling point is 82-83°C (2.13kPa), its relative density is 1.122, and its refractive index is 1.5352 (25°C). Flash point is 54° C. 4-Pyridinecarboxaldehyde is soluble in water and ether.4-Pyridinecarboxaldehyde, also commonly called pyridine-2-carboxaldehyde, is an organic compound with the formula NC5H4CHO. 4-Pyridinecarboxaldehyde is a colorless oily liquid with a distinctive odor. Older samples are often brown-colored owing to impurities.4-Pyridinecarboxaldehyde can be analyzed by this reverse phase (RP) HPLC method with simple conditions. The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid. For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. Smaller 3 µm particles columns available for fast UPLC applications. This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation. 4-Pyridinecarboxaldehyde also suitable for pharmacokinetics.

Fig 1. Chemical structure formula and three-dimensional structure of 4-Pyridinecarboxaldehyde

4-Pyridinecarboxaldehyde is an heterocyclic building block used for the synthesis of various pharmaceutical compounds, such as new 1,4-dihydropyridin-4-yl-phenoxyacetohydrazones, having anticonvulsant and anti-inflammatory properties[1,2].

4-Pyridinecarboxaldehyde was shown to be an efficient building block for synthesis of Schiff bases using a Korich-type reaction, an intermolecular reductive synthetic procedure based on the condensation of nitro-substituted arenes and aromatic aldehydes in the presence of iron powder and dilute acid. Metal complexes of several of these Schiff bases were shown to exhibit good activity against different types of bacteria (e.g., Staphylococcus aureus, E. coli, Klebsiella, Pneumonia) and fungi (Candida albicans, Apergillus niger and Pencillium sp), and also moderate nuclease activity. 4-Pyridinecarboxaldehyde and some of its derivatives have also been reported as useful transamination reagents to introduce ketone or aldehyde groups onto the N-termini of antibodies for subsequent site-specifically conjugate aminooxy-functionalized molecules (including fluorescent dyes, polyethylene glycol, or porphyrins) to these entities[3-6].

4-Pyridinecarboxaldehyde can be used for the synthesis of: β-Unsaturated amides by coupling with N,N-disubstituted formamides; meso-Substituted A3-corroles; N-(4-pyridylmethyl)-L-valine as a ligand to construct zinc metal–organic frameworks (Zn-MOFs); 4′-Pyridyl terpyridines, with potential application as anticancer and antimicrobial agents; 4-pyridinecarboxaldehyde thiosemicarbazone, as a corrosion inhibitor for mild steel.

References

[1] A.Martin; B.Lucke; H.J.Niclas; A.Forster. Vapor-phase oxidation of 4-picoline to pyridine-4-carboxaldehyde on a vanadium phosphate catalysts. Reaction Kinetics and Catalysis Letters. 1991, 43, (2),583-588.
[2] Nand K.Singh; Rajesh Tripathi. Synthesis and structural characterization of 3d-metal complexes of pyridine-4-carboxaldehyde thionicotinoyl hydrazone. Transition Metal Chemistry. 1988, 13, (5),346-350.
[3] P.V. Rao, A.V.G.S. Prasad, P.S.S. Prasad Int. J. Pharm. Develop. Technol., 4 (2014), pp. 245-248.
[4] Andrew Korich, Thomas Hughes. A Facile, One-Pot Procedure for Forming Diarylimines from Nitroarenes and Benzaldehydes[J]. Cheminform, 2007(16):2602-2604.

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