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Pyridine-2-carbaldehyde

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Pyridine-2-carbaldehyde
Picolinaldehyde
Names
Preferred IUPAC name Pyridine-2-carbaldehyde
Other names Picolinaldehyde
2-Pyridine carboxaldehyde
2-Pyridyl aldehyde
Picolinal
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.013.031 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5NO/c8-5-6-3-1-2-4-7-6/h1-5HKey: CSDSSGBPEUDDEE-UHFFFAOYSA-N
SMILES
  • O=Cc1ncccc1
Properties
Chemical formula C6H5NO
Molar mass 107.112 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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.

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. Iminopyridine complexes can be remarkably robust.

References

  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. ISBN 978-3527306732.
  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.
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