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4-Pyridone

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4-Pyridone
Names
Preferred IUPAC name Pyridin-4(1H)-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.304 Edit this at Wikidata
EC Number
  • 203-633-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)Key: GCNTZFIIOFTKIY-UHFFFAOYSA-N
  • InChI=1/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)Key: GCNTZFIIOFTKIY-UHFFFAOYAB
SMILES
  • c1cccc1=O
Properties
Chemical formula C5H5NO
Molar mass 95.101 g·mol
Appearance colorless solid
Melting point 150 °C (302 °F; 423 K)
Boiling point 181 °C (358 °F; 454 K)
Solubility in water Soluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

4-Pyridone is an organic compound with the formula C
5H
4NH(O). It is a colorless solid.

Preparation

4-Pyridone, and its derivatives, are prepared from 4-pyrone and amines in protic solvents.

Tautomerism

4-Pyridone exists a keto-enol tautomerism with its enol tautomer 4-hydroxypyridine. In solution, the keto tautomer is favoured, and the enol tautomer only becomes important in very dilute solutions or solutions of non-polar solvents. However, the enol tautomer is dominant in the gas phase.

Derivatives

Fluridone is an aquatic herbicide that contains a 4-pyridone subunit.

Chemical structure of fluridone

See also

References

  1. Weygand, Conrad (1972). Hilgetag, G.; Martini, A. (eds.). Weygand/Hilgetag Preparative Organic Chemistry (4th ed.). New York: John Wiley & Sons, Inc. pp. 533–534. ISBN 0471937495.
  2. Van Allan, J. A.; Reynolds, G. A.; Alessi, J. T.; Chie Chang, S.; C. Joines, R. (1971). "Reactions of 4-pyrones with primary amines. A new class of ionic associates". Journal of Heterocyclic Chemistry. 8 (6): 919–922. doi:10.1002/jhet.5570080606.
  3. Cook, Denys (1963). "The Preparation, Properties, and Structure of 2,6-bis-(Alkyamino)-2,5-heptadien-4-ones". Canadian Journal of Chemistry. 41 (6): 1435–1440. doi:10.1139/v63-195.
  4. Entry on Pyridinole. at: Römpp Online. Georg Thieme Verlag, retrieved 2014-09-29.
  5. Joule, John A.; Mills, Keith (2000-06-29). Heterocyclic Chemistry. Oxford: Wiley-Blackwell. p. 88-91. ISBN 0-632-05453-0.
  6. Müller, Franz; Applebyki, Arnold P. (2011). "Weed Control, 2. Individual Herbicides". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.o28_o01. ISBN 978-3-527-30385-4.
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