Pyridine-2-carbaldehyde

Pyridine-2-carbaldehyde, also called 2-formylpyridine, is an organic compound with the formula NC₅H₄CHO. It is one of three isomeric pyridinaldehydes. The other isomers are pyridine-3-carboxaldehyde and pyridine-4-carboxaldehyde.

Pyridine-2-carbaldehyde

Picolinaldehyde
Names
Preferred IUPAC name Pyridine-2-carbaldehyde
Other names Picolinaldehyde 2-Pyridine carboxaldehyde 2-Pyridyl aldehyde Picolinal
Identifiers
CAS Number	1121-60-4 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL274794 Y
ChemSpider	13635 Y
ECHA InfoCard	100.013.031
PubChem CID	14273
UNII	KH86K8FHZ2 Y
CompTox Dashboard (EPA)	DTXSID1061522
InChI InChI=1S/C6H5NO/c8-5-6-3-1-2-4-7-6/h1-5H Y Key: CSDSSGBPEUDDEE-UHFFFAOYSA-N Y
SMILES O=Cc1ncccc1
Properties
Chemical formula	C6H5NO
Molar mass	107.112 g·mol−1
Density	1.126 g/mL
Melting point	148–151 °C (298–304 °F; 421–424 K)
Boiling point	181 °C (358 °F; 454 K)
Related compounds
Related Aldehydes	Salicylaldehyde Quinoline Carboxaldehyde
Related compounds	Picolinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 and pharmaceuticals. Pyridine aldehydes are typically prepared by oxidation of the hydroxymethyl- or methylpyridines.^[1]

Reactions and uses

The drug pralidoxime can be produced from 2-formylpyridine.

The aldehyde functional group is subject to nucleophilic attack, specifically by amines to form Schiff bases, which serve as bidentate ligands.^[2] Iminopyridine complexes can be remarkably robust.^[3]