Iodopyridine
Iodopyridine describes organoiodine compounds that consist of a pyridine ring wherein one or more hydrogen atoms is substituted by one or more iodide.
| Iodopyridines | |||
| IUPAC name | 2-iodopyridine | 3-iodopyridine | 4-iodopyridine |
| Chemical structure |  |
 |
 |
| CAS number | 5029-67-4 | 1120-90-7 | 15854-87-2 |
| PubChem | CID 221126 from PubChem | CID 70714 from PubChem | CID 609492 from PubChem |
| Chemical formula | IC5H4N | ||
| Molar mass | 205 g/mol | ||
| Appearance | colorless solid | colorless solid | colorless solid |
| Melting point | 118–120 °C | 52–53 °C | 98–99 °C |
| Boiling point | 202–203 °C | 40 °C (10 Torr) | – |
| Density | 1.928 g/cm3 | – | – |
Preparations
[edit]4-Iodopyridine can be prepared from 4-aminopyridine via diazotization followed by treatment with copper(I) iodide.[1] 2-Iodopyridine can also be produced via diazotization, but a copper-catalyzed salt metathesis method from 2-chloropyridine is simpler[2]
Applications
[edit]A known use of 2-iodopyridine is in the synthesis of dipraglurant (patented, last step is a Sonogashira coupling reaction).
A known use of 3-iodopyridine is in the synthesis of CI-844 (3-Phenoxypyridine).[3][4]
Related compounds
[edit]References
[edit]- ↑ Coudret, C. (1996). "Efficient Syntheses of 4-Iodopyridine and of 4-Pyridylboronic Acid Pinacol Ester". Synthetic Communications. 26 (19): 3543–3547. doi:10.1080/00397919608003763.
- ↑ Klapars, Artis; Buchwald, Stephen L. (2002). "Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction". Journal of the American Chemical Society. 124 (50): 14844–14845. doi:10.1021/ja028865v. PMID 12475315.
- ↑ Owen, R. T. (1985). "CI-844". Drugs of the Future. 10 (4): 279. doi:10.1358/dof.1985.010.04.65203. ISSN 0377-8282. Retrieved 9 September 2026.
- ↑ Butler, D. E., Poschel, B. P. H., Marriott, J. G. (March 1981). "Cognition-activating properties of 3-(aryloxy)pyridines". Journal of Medicinal Chemistry. 24 (3): 346–350. doi:10.1021/jm00135a020. Retrieved 9 September 2026.