4-(2-Pyridyl)benzoic acid Chemical Properties

Melting point:

236.0 to 240.0 °C

Boiling point:

388.1±25.0 °C(Predicted)

Density 

1.241±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

3.17±0.10(Predicted)

color 

White to Light Grey

CAS DataBase Reference

4385-62-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933399990

4-(2-Pyridyl)benzoic acid Usage And Synthesis

Uses

Reactive metabolite of Atazanavir (A790051). Atazanavir Impurity (Pyridinyl Benzoic Acid)

Synthesis

Example 10: Synthesis of 4-(2-pyridyl)benzoic acid In a 100 mL jacketed reactor, 200 mL of acetic acid, 0.05 g of manganese(II) acetate, 1.74 g of sulfuric acid, and 3.0 g of 2-(4-methylphenyl)pyridine were sequentially added. The reaction mixture was cooled to 16°C, followed by slow passage of 4.0 g of ozone over 60 minutes. Upon completion of the ozonolysis reaction, the reaction was purged with nitrogen to remove residual ozone from the solvent. The reaction mixture was analyzed by HPLC or GC, which showed that the residue of 2-(4-methylphenyl)pyridine was <0.1% and the yield of 4-(2-pyridyl)benzoic acid was 94-97%.

References

[1] Patent: US2003/216577, 2003, A1. Location in patent: Page/Page column 4
[2] Dyes and Pigments, 2017, vol. 140, p. 269 - 277
[3] Dyes and Pigments, 2011, vol. 91, # 3, p. 413 - 421
[4] Journal of the Chemical Society, 1956, p. 100,101
[5] Patent: US5854264, 1998, A

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