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-iodopyridine3-iodopyridine4-iodopyridine
Chemical structure Structure of 2-iodopyridine Structure of 3-iodopyridine Structure of 4-iodopyridine
CAS number 5029-67-41120-90-715854-87-2
PubChem CID 221126 from PubChemCID 70714 from PubChemCID 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

4-Iodopyridine can be prepared from 4-aminopyridine via diazotization followed by treatment with copper(I) iodide. 2-Iodopyridine can also be produced via diazotization, but a copper-catalyzed salt metathesis method from 2-chloropyridine is simpler

Applications

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).

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.