4-Pyridone
Names
Preferred IUPAC name
Pyridin-4(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.304
EC Number
  • 203-633-2
UNII
  • InChI=1S/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7) checkY
    Key: GCNTZFIIOFTKIY-UHFFFAOYSA-N checkY
  • InChI=1/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)
    Key: GCNTZFIIOFTKIY-UHFFFAOYAB
  • c1c[nH]ccc1=O
Properties
C5H5NO
Molar mass 95.101 g·mol−1
Appearance colorless solid
Melting point 150 °C (302 °F; 423 K)
Boiling point 181 °C (358 °F; 454 K)
Soluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[1][2][3]

Tautomerism

4-Pyridone exists a keto-enol tautomerism with its enol tautomer 4-hydroxypyridine. In solution, the keto tautomer is favoured,[4] 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.[5]

Derivatives

Fluridone is an aquatic herbicide that contains a 4-pyridone subunit.[6]

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. ↑ Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry, 2010, doi:10.1002/14356007.o28_o01
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