2-Pyrone

2-Pyrone
Names
Preferred IUPAC name
2H-Pyran-2-one
Other names
α-Pyrone
2-Pyranone
Pyran-2-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.264
UNII
  • InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H Y
    Key: ZPSJGADGUYYRKE-UHFFFAOYSA-N Y
  • InChI=1/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H
    Key: ZPSJGADGUYYRKE-UHFFFAOYAI
  • O=C\1O\C=C/C=C/1
Properties
C5H4O2
Molar mass 96.085 g·mol−1
Density 1.197 g/mL
Boiling point 102 to 103 °C (216 to 217 °F; 375 to 376 K) at 20 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

2-Pyrone (α-pyrone or pyran-2-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 4-pyrone.

2-Pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. For example, it readily undergoes Diels-Alder reactions with alkynes producing, upon loss of carbon dioxide, substituted benzenes. The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.

The parent 2-pyrone can be produced from decarboxylation of coumalic acid.

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