4-Pyridone

4-Pyridone

Names
Preferred IUPAC name Pyridin-4(1H)-one
Identifiers
CAS Number	108-96-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:133125
ChEMBL	ChEMBL237459
ChemSpider	11787^Y
ECHA InfoCard	100.003.304
EC Number	203-633-2
PubChem CID	12290
UNII	3P2MV07G53^Y
CompTox Dashboard (EPA)	DTXSID2052310
InChI InChI=1S/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)^Y Key: GCNTZFIIOFTKIY-UHFFFAOYSA-N^Y InChI=1/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7) Key: GCNTZFIIOFTKIY-UHFFFAOYAB
SMILES c1c[nH]ccc1=O
Properties
Chemical formula	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)
Solubility in water	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

• 2-Pyridone
• 4-Piperidone
• Dehydroacetic acid

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.