4-Pyridinecarboxaldehyde

Flavor Type

Flavor Type: fruity

Chemical Properties

4-Pyridinecarboxaldehyde(4PCA) is a slightly yellow oily liquid. 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.

Uses

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.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.
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.

Chemical Properties

clear yellow-brown liquid. soluble in water and ether.

Uses

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.

Uses

4-Pyridinecarboxaldehyde can be used for the synthesis of:

• γ,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.

Application

As a colorless liquid with a pungent odor, 4-Pyridinecarboxaldehyde serves as a component in the synthesis of diverse organic compounds. Its applications extend to the synthesis of pharmaceuticals, fragrances, and pesticides. Moreover, it has proven instrumental in the creation of a wide range of organic compounds, including antioxidants and anti-inflammatory agents.

Preparation

4-Pyridinecarbaldehyde is synthesized by oxidation of 4-picoline. The mixed gas of 4-picoline and air is passed through the vanadium-molybdenum catalyst layer heated to 400°C, and oxidized to generate 4-pyridinecarbaldehyde.

Reactions

4-Pyridinecarboxaldehyde undergoes many reactions expected for aromatic aldehydes such as reductive amination and Schiff base formation. It condenses with pyrrole to give tetrapyridylporphyrin.

Synthesis Reference(s)

Synthetic Communications, 20, p. 3385, 1990 DOI: 10.1080/00397919008051576

Purification Methods

Purified as for pyridine-2-aldehyde. [Beilstein 21 III/IV 2529, 21/7 V 351.]