4-Pyridone is an organic compound with the formula C
5H
4NH(O). It is a colorless solid.
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| Preferred IUPAC name
Pyridin-4(1H)-one | |
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3D model (JSmol)
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| ECHA InfoCard | 100.003.304 |
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CompTox Dashboard (EPA)
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| 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).
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Preparation
edit4-Pyridone, and its derivatives, are prepared from 4-pyrone and amines in protic solvents.[1][2][3]
Tautomerism
edit4-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
editFluridone is an aquatic herbicide that contains a 4-pyridone subunit.[6]
Chemical structure of fluridone
See also
editReferences
edit- ^ 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.
- ^ 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.
- ^ 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.
- ^ Entry on Pyridinole. at: Römpp Online. Georg Thieme Verlag, retrieved 2014-09-29.
- ^ Joule, John A.; Mills, Keith (2000-06-29). Heterocyclic Chemistry. Oxford: Wiley-Blackwell. p. 88-91. ISBN 0-632-05453-0.
- ^ 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.