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Pyrimidone

From Wikipedia, the free encyclopedia
Pyrimidone
2-Pyrimidone
2-Pyrimidone
4-Pyrimidone
4-Pyrimidone
Names
Preferred IUPAC name
1H-Pyrimidin-6-one
Other names
Hydroxypyrimidine; Pyrimidinone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H4N2O/c7-4-1-2-5-3-6-4/h1-3H,(H,5,6,7)
    Key: DNCYBUMDUBHIJZ-UHFFFAOYSA-N
  • O=C1NC=NC=C1
Properties
C4H4N2O
Molar mass 96.089 g·mol−1
Appearance White to light yellow powder
Melting point 163 to 168 °C (325 to 334 °F; 436 to 441 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Respiratory system, eye, skin irritation
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

Pyrimidone is the name given to either of two heterocyclic compounds with the formula C4H4N2O: 2-pyrimidone[1] and 4-pyrimidone. The compounds can also be called 2-hydroxypyrimidine or 4-hydroxypyrimidine respectively, based on a substituted pyrimidine, or 1,3-diazine, ring.

Applications

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Derivatives

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Derivatives of pyrimidone are the basis of many other biological molecules, including:

Pyrimidone-derived antiulcer drugs include temelastine, icotidine, donetidine, and lupitidine.

Methylated pyrimidone derivatives undergo pH-switched photoisomerization to the corresponding Dewar arene. The process can be used for long-term thermal energy storage with an energy density of 1.6 MJ/kg[2], approximately double that of a lithium ion battery.


References

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  1. Manglik, Mr Rohit (23 June 2023). Basics of Organic Chemistry. EduGorilla Publication. p. 430. ISBN 978-93-6817-864-4.
  2. Nguyen, Han P. Q.; Maertens, Alexander J.; Baker, Benjamin A.; Wu, Nathan M.-W.; Ye, Zihao; Zhou, Qingyang; Qiu, Qianfeng; Kaur, Navneet; Berkinsky, David B.; Shulenberger, Katherine E.; Houk, K. N.; Han, Grace G. D. (2026-02-12). "Molecular solar thermal energy storage in Dewar pyrimidone beyond 1.6 MJ/kg". Science. 0 (0) eaec6413. doi:10.1126/science.aec6413.