Pyrimidone

Pyrimidone
2-Pyrimidone	4-Pyrimidone
Names
	Preferred IUPAC name 1H-Pyrimidin-6-one
	Other names Hydroxypyrimidine; Pyrimidinone
Identifiers
CAS Number	557-01-7 2-Pyrimidone ; 4562-27-0 4-Pyrimidone [CAS];
3D model (JSmol)	Interactive image;
ChemSpider	61686 2-Pyrimidone; 19489 4-Pyrimidone;
PubChem CID	20695;
UNII	13K708ILY4 2-Pyrimidone ; K43V90OY4L 4-Pyrimidone ;
	InChI InChI=1S/C4H4N2O/c7-4-1-2-5-3-6-4/h1-3H,(H,5,6,7) Key: DNCYBUMDUBHIJZ-UHFFFAOYSA-N;
	SMILES O=C1NC=NC=C1;
Properties
Chemical formula	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). verify (what is ?) Infobox references

Pyrimidone is the name given to either of two heterocyclic compounds with the formula C₄H₄N₂O: 2-pyrimidone 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

Derivatives

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

Nucleobases, such as cytosine
Barbiturates, such as metharbital

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, approximately double that of a lithium ion battery.

References

↑ Manglik, Mr Rohit (23 June 2023). Basics of Organic Chemistry. EduGorilla Publication. p. 430. ISBN 978-93-6817-864-4.
↑ 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. 392 (6796) eaec6413. doi:10.1126/science.aec6413. S2CID 285548022.

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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.

[:0-2] 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. 392 (6796) eaec6413. doi:10.1126/science.aec6413. S2CID 285548022.