Pyridine-2-carbaldehyde, also called 2-formylpyridine, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula NC₅H₄CHO. It is one of three isomeric pyridinaldehydes. The other isomers are pyridine-3-carboxaldehyde and

pyridine-4-carboxaldehyde Pyridine-4-carbaldehyde is an organic compound with the formula C5H4NCHO. It is one of three isomeric pyridinaldehydes. The other isomers are pyridine-2-carboxaldehyde and pyridine-3-carboxaldehyde. Pyridine-4-carboxaldehyde is a colorless liqui ...

. Pyridine-2-carbaldehyde is a colorless oily liquid with a distinctive odor. Older samples are often brown-colored owing to impurities. It serves as a precursor to other compounds of interest in

coordination chemistry A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

and

pharmaceutical A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and re ...

s. Pyridine aldehydes are typically prepared by oxidation of the hydroxymethyl- or methylpyridines.

Reactions and uses

The drug

pralidoxime Pralidoxime (2-pyridine aldoxime methyl chloride) or 2-PAM, usually as the chloride or iodide salts, belongs to a family of compounds called oximes that bind to organophosphate-inactivated acetylcholinesterase. It is used to treat organophosphat ...

can be produced from 2-formylpyridine. The aldehyde functional group is subject to nucleophilic attack, specifically by amines to form

Schiff bases In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines or secondary aldimines ...

, which serve as bidentate ligands. Iminopyridine complexes can be remarkably robust.

References

{{reflist Aromatic aldehydes 2-Pyridyl compounds