4-Pyrid-4-ylbenzoic acid Chemical Properties

Melting point:

>300°C

Boiling point:

384.3±25.0 °C(Predicted)

Density 

1.241±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

3?+-.0.10(Predicted)

form 

solid

Appearance

White to off-white Solid

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C12H9NO2/c14-12(15)11-3-1-9(2-4-11)10-5-7-13-8-6-10/h1-8H,(H,14,15)

InChIKey

DZLGZIGLHCRIMF-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(C2C=CN=CC=2)C=C1

CAS DataBase Reference

4385-76-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-22-37

HazardClass 

IRRITANT

HS Code 

29333990

4-Pyrid-4-ylbenzoic acid Usage And Synthesis

Synthesis

Example 159 A Synthesis of 4-(pyridin-4-yl)benzoic acid: To a mixed solvent of acetonitrile (40 mL) and water (40 mL) was added 4-carboxyphenylboronic acid (1.66 g, 10 mmol), 4-bromopyridine (1.72 g, 11 mmol), potassium carbonate (5.5 g, 40 mmol), and bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol). The reaction mixture was degassed and displaced three times with nitrogen. Subsequently, the mixture was stirred at 100 °C for 24 hours. Upon completion of the reaction, the reaction suspension was filtered while hot and the filtrate was concentrated to half of the original volume. The concentrated aqueous phase was washed with dichloromethane, and then the pH of the aqueous phase was adjusted with 1 M hydrochloric acid to 3. The precipitated solid was collected by filtration, washed with water, and finally dried under vacuum to give 1.8 g of the white solid product, 4-(pyridin-4-yl)benzoic acid, in 90% yield.LC-MS (ESI) m/z: 200(M+1)+.

References

[1] Archiv der Pharmazie, 2008, vol. 341, # 8, p. 478 - 484
[2] Patent: US2009/197863, 2009, A1. Location in patent: Page/Page column 74

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