6-(1H-Pyrazol-1-yl)nicotinic acid Chemical Properties

Melting point:

272-274℃

Boiling point:

394.6±27.0 °C(Predicted)

Density 

1.39±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

3.28±0.10(Predicted)

color 

White to off-white

CAS DataBase Reference

253315-22-9

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29333990

6-(1H-Pyrazol-1-yl)nicotinic acid Usage And Synthesis

Chemical Properties

White solid

Synthesis

Compound 1 (CAS: 1428929-49-0, 8.66 g, 40.43 mmol, 1.0 eq.) was dissolved in anhydrous ethanol (80 mL), followed by slow addition of 3 M aqueous sodium hydroxide solution (40.40 mL, 121.3 mmol, 3.0 eq.). The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solvent was removed by reduced pressure distillation and the residue was dissolved in deionized water (60 mL). The aqueous phase was extracted twice with ether (40 mL × 2) to remove organic impurities. Subsequently, the pH of the aqueous phase was adjusted to 3 with 2 M aqueous hydrochloric acid, at which time a white solid precipitated. The white solid was collected by filtration and dried to give 6-(1H-pyrazol-1-yl)nicotinic acid (7.42 g, 97% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 6.65 (dd, J = 2.7, 1.6 Hz, 1H, Ar-H), 7.92 (dd, J = 1.6, 0.8 Hz, 1H, Ar-H), 8.04 (dd, J = 8.6, 0.8 Hz, 1H, Ar-H), 8.44 (dd, J = 8.6 , 2.3 Hz, 1H, Ar-H), 8.70 (dd, J = 2.7, 0.8 Hz, 1H, Ar-H), 8.96 (dd, J = 2.3, 0.8 Hz, 1H, Ar-H), 13.44 (s, 1H, COOH).

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 68 - 90
[2] Patent: WO2014/85210, 2014, A1. Location in patent: Page/Page column 40

6-(1H-Pyrazol-1-yl)nicotinic acid(253315-22-9)Related Product Information

• Nicotinic acid
• Folic acid
• 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
• Pyridine
• Chromium picolinate
• Glycine
• Zolpidem tartrate
• 2-Picolinic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Pyraclostrobin
• Zolpidem
• Methyl 6-(1H-pyrazol-1-yl)pyridine-3-carboxylate
• CARBOXYLIC ACID
• 6-(1H-Pyrazol-1-yl)nicotinic acid
• 5-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)nicotinic acid
• DIETHYL 2-(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-6-HYDROXY-3,5-PYRIDINEDICARBOXYLATE
• 6-(4-nitro-1H-pyrazol-1-yl)pyridine-3-carboxylic acid
• 5-chloro-6-(1H-pyrazol-1-yl)nicotinic acid