2-pyrimidinone

Structural formula
General
Surname	2-pyrimidinone
other names	2 (1 H ) -pyrimidinone ( IUPAC ) ; 2-hydroxypyrimidine; 2-pyrimidinol;
Molecular formula	C 4 H 4 N 2 O
Brief description	light yellow solid
External identifiers / databases
EC number	209-149-8
ECHA InfoCard	100.008.319
PubChem	68401
ChemSpider	61686
Wikidata	Q17572764
properties
Molar mass	96.09 g mol −1
Physical state	firmly
density	1.37 g cm −3
Melting point	179-181 ° C
solubility	very soluble in water
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-pyrimidinone is a chemical compound from the group of pyrimidines . The connection corresponds to the basic structure of many nucleobases such as B. the cytosine .

Extraction and presentation

The compound can be obtained by the oxidation of 2-chloropyrimidine with hydrogen peroxide .

properties

2-pyrimidinone is a crystalline solid that occurs in a tetragonal crystal lattice with the space group P 4 ₁ 2 ₁ 2 (space group no. 92) . A tautomeric equilibrium can be formulated for the compound with a keto and an enol form. Quantum chemical calculations show that the keto structure is the more stable form. Template: room group / 92

Individual evidence

↑ Fargher, RG; Pyman, FL: XXVI.-Nitro-, arylazo-, and amino-glyoxalines in J. Chem. Soc. 115 (1919) 217-260, doi : 10.1039 / CT9191500217 .
↑ ^a ^b Furberg, S .; Solbakk, J .: Crystal Structure of Pyrimidine-2-one in Acta Chem. Scand. 24 (1970) 3230-3236, doi : 10.3891 / acta.chem.scand.24-3230 .
↑ Hunt, RR; McOmie, JFW; Sayer, ER: 109. Pyrimidines. Part X. Pyrimidine, 4: 6-dimethylpyrimidine, and their 1-oxides in J. Chem. Soc. 1959, 525-530, doi : 10.1039 / JR9590000525 .
↑ Albert, A .; Brown, DJ; Cheeseman, G .: 812. Pteridine studies. Part III. The solubility and the stability to hydrolysis of pteridines in J. Chem. Soc. 1952, 4219-4232, doi : 10.1039 / JR9520004219 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Cantrell Jr., WR; Bauta, WE; Engles, T .: Hydrogen peroxide promoted hydroxylation of haloarenes and heteroarenes in Tetrahedron Lett. 47 (2006) 4249-4251, doi : 10.1016 / j.tetlet.2006.04.020 .
↑ Les, A .; Adamowicz, L .: Theoretical ab initio study of the protomeric tautomerism of 2-hydroxypyrimidine, 4-hydroxypyrimidine, and their derivatives in J. Phys. Chem. 94 (1990) 7012-7032, doi : 10.1021 / j100381a020 .
↑ Cieplak, P .; Bash, P .; Singh, CU; Kollman, PA: A theoretical study of tautomerism in the gas phase and aqueous solution: a combined use of state-of-the-art ab initio quantum mechanics and free energy-perturbation methods in J. Am. Chem. Soc. 109 (1987) 6283-6289, doi : 10.1021 / ja00255a010 .

[1] Fargher, RG; Pyman, FL: XXVI.-Nitro-, arylazo-, and amino-glyoxalines in J. Chem. Soc. 115 (1919) 217-260, doi : 10.1039 / CT9191500217 .

[Furberg-2] Furberg, S .; Solbakk, J .: Crystal Structure of Pyrimidine-2-one in Acta Chem. Scand. 24 (1970) 3230-3236, doi : 10.3891 / acta.chem.scand.24-3230 .

[3] Hunt, RR; McOmie, JFW; Sayer, ER: 109. Pyrimidines. Part X. Pyrimidine, 4: 6-dimethylpyrimidine, and their 1-oxides in J. Chem. Soc. 1959, 525-530, doi : 10.1039 / JR9590000525 .

[4] Albert, A .; Brown, DJ; Cheeseman, G .: 812. Pteridine studies. Part III. The solubility and the stability to hydrolysis of pteridines in J. Chem. Soc. 1952, 4219-4232, doi : 10.1039 / JR9520004219 .

[NV-5] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[6] Cantrell Jr., WR; Bauta, WE; Engles, T .: Hydrogen peroxide promoted hydroxylation of haloarenes and heteroarenes in Tetrahedron Lett. 47 (2006) 4249-4251, doi : 10.1016 / j.tetlet.2006.04.020 .

[Les-7] Les, A .; Adamowicz, L .: Theoretical ab initio study of the protomeric tautomerism of 2-hydroxypyrimidine, 4-hydroxypyrimidine, and their derivatives in J. Phys. Chem. 94 (1990) 7012-7032, doi : 10.1021 / j100381a020 .

[Kollman-8] Cieplak, P .; Bash, P .; Singh, CU; Kollman, PA: A theoretical study of tautomerism in the gas phase and aqueous solution: a combined use of state-of-the-art ab initio quantum mechanics and free energy-perturbation methods in J. Am. Chem. Soc. 109 (1987) 6283-6289, doi : 10.1021 / ja00255a010 .