2-Formylpyridine
 | |
| Names | |
|---|---|
| Preferred IUPAC name
Pyridine-2-carbaldehyde | |
| Other names
Picolinaldehyde 2-Pyridine carboxaldehyde 2-Pyridyl aldehyde Picolinal | |
| Identifiers | |
1121-60-4  | |
| 3D model (Jmol) | Interactive image |
| ChEMBL | ChEMBL274794 |
| ChemSpider | 13635 |
| ECHA InfoCard | 100.013.031 |
| PubChem | 14273 |
| |
| |
| 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
- ↑ 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.
- ↑ 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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