6-Hydroxypyrimidine-4-carboxylic acid Chemical Properties

Melting point:

268-270 °C

Boiling point:

305.2±52.0 °C(Predicted)

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

pka

2.77±0.20(Predicted)

color 

White to Light yellow to Light red

InChI

InChI=1S/C5H4N2O3/c8-4-1-3(5(9)10)6-2-7-4/h1-2H,(H,9,10)(H,6,7,8)

InChIKey

QYGHXDAYBIFGKI-UHFFFAOYSA-N

SMILES

C1NC(=O)C=C(C(O)=O)N=1

CAS DataBase Reference

6299-87-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

HS Code 

29335990

6-Hydroxypyrimidine-4-carboxylic acid Usage And Synthesis

Uses

As the main formic acid derivative, 6-Hydroxypyrimidine-4-carboxylic acid has the antibacterial ability of formic acid, while overcoming the irritation and corrosiveness of formic acid. It is widely used in feed and aquaculture. As an organic acid with a relatively simple structure, 6-Hydroxypyrimidine-4-carboxylic acid has good acidification and nutritional functions.

Synthesis

In a 1 L round bottom flask, 55 g of sodium ethoxyzine acetate (1.05 eq., 0.26 mol) and 26 g of formamidine acetate (1 eq., 0.25 mol) were added to a 500 mL aqueous solution containing 10 g of sodium hydroxide. The reaction mixture was stirred at room temperature for 16 hours. Subsequently, concentrated hydrochloric acid was added slowly and dropwise to the reaction mixture until the pH dropped to 1, at which point fine solids precipitated. The mixture was continued to be stirred at 0°C for 1 hour to complete the precipitation. The solid product was collected by filtration and washed sequentially with water and ether. The resulting white solid was dried in a vacuum oven preheated to 40°C for 20 hours. Finally, grinding in methanol afforded the target compound 6-hydroxy-4-pyrimidinecarboxylic acid in 25% yield.1H NMR (dβ-DMSO) data were as follows: δ 12.88 (1H, OH), 8.24 (s, 1H), 6.83 (s, 1H).

References

[1] Patent: WO2010/20432, 2010, A2. Location in patent: Page/Page column 91
[2] European Journal of Medicinal Chemistry, 2018, vol. 149, p. 30 - 44
[3] Patent: US2011/21500, 2011, A1. Location in patent: Page/Page column 39
[4] Patent: US2011/59954, 2011, A1. Location in patent: Page/Page column 71
[5] Patent: US2011/172218, 2011, A1. Location in patent: Page/Page column 28

6-Hydroxypyrimidine-4-carboxylic acid(6299-87-2)Related Product Information

• 6-Hydroxyindazole
• 6-Hydroxyindole
• Isoquinolin-6-ol
• 5-IODOOROTIC ACID
• Orotic acid
• 2-AMINO-6-HYDROXY-PYRIMIDINE-4-CARBOXYLIC ACID
• 2,4-DIMETHOXYPYRIMIDINE-6-CARBOXYLIC ACID
• 6-Oxo-3H-pyrimidine-4-carboxylic acid
• 2-Pyrimidinecarboxylic acid, 5-hydroxy- (9CI)
• Ethyl 4-hydroxypyrimidine-5-carboxylate
• 2-Oxo-3H-pyrimidine-4-carboxylic acid
• 4-Hydroxypyrimidine-5-carboxylic acid methyl ester
• 4-Pyrimidinecarboxylic acid
• 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-1-METHYL-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER
• 6-Hydroxy-2-(methylsulfanyl)-4-pyrimidinecarboxylic acid
• 5-CHLORO-2-CYCLOPROPYL-6-OXO-1,6-DIHYDRO-PYRIMIDINE-4-CARBOXYLIC ACID
• 2-CYCLOPROPYL-6-OXO-1,6-DIHYDRO-PYRIMIDINE-4-CARBOXYLIC ACID
• 5H-THIAZOLO[3,2-A]PYRIMIDINE-7-CARBOXYLIC ACID, 5-OXO-