2-Formylpyridine

2-Formylpyridine
Names
Preferred IUPAC name
Pyridine-2-carbaldehyde
Other names
Picolinaldehyde
2-Pyridine carboxaldehyde
2-Pyridyl aldehyde
Picolinal
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.031
Properties
C6H5NO
Molar mass 107.11 g·mol−1
Density 1.126 g/mL
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

2-Formylpyridine, also commonly called pyridine-2-carboxaldehyde, is an organic compound with the formula NC5H4CHO. It 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

  1. ↑ Shinkichi Shimizu; Nanao Watanabe; Toshiaki Kataoka; Takayuki Shoji; Nobuyuki Abe; Sinji Morishita; Hisao Ichimura (2002). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. 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. PMID 19556504. doi:10.1126/science.1175313.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.