Pyridine-2-carbaldehyde

Pyridine-2-carbaldehyde
Names
	Preferred IUPAC name Pyridine-2-carbaldehyde
	Other names Picolinaldehyde; 2-Pyridine carboxaldehyde; 2-Pyridyl aldehyde ; Picolinal
Identifiers
CAS Number	1121-60-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL274794 ;
ChemSpider	13635 ;
ECHA InfoCard	100.013.031
PubChem CID	14273;
UNII	KH86K8FHZ2 ;
CompTox Dashboard (EPA)	DTXSID1061522 ;
	InChI InChI=1S/C6H5NO/c8-5-6-3-1-2-4-7-6/h1-5H Key: CSDSSGBPEUDDEE-UHFFFAOYSA-N ;
	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, 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 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]

References

Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.
Chatterjeea, D.; Mitra, A. (2004). "Synthesis, Characterization and Reactivities of Schiff-base Complexes of Ruthenium(III)". J. Coord. Chem. 57: 175–182. doi:10.1080/00958970410001662435.
Mal, P.; Breiner, B.; Rissanen, K.; Nitschke, J. R. (2009). "White Phosphorus is Air-Stable Within a Self-Assembled Tetrahedral Capsule". Science. 324 (5935): 1697–1699. doi:10.1126/science.1175313. PMID 19556504.

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[Ullmann-1] Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.

[2] Chatterjeea, D.; Mitra, A. (2004). "Synthesis, Characterization and Reactivities of Schiff-base Complexes of Ruthenium(III)". J. Coord. Chem. 57: 175–182. doi:10.1080/00958970410001662435.

[3] Mal, P.; Breiner, B.; Rissanen, K.; Nitschke, J. R. (2009). "White Phosphorus is Air-Stable Within a Self-Assembled Tetrahedral Capsule". Science. 324 (5935): 1697–1699. doi:10.1126/science.1175313. PMID 19556504.