3-(3-PYRIDINYL)BENZOIC ACID Chemical Properties

Melting point:

202-205.5

Boiling point:

420.1±28.0 °C(Predicted)

Density 

1.241±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

3.78±0.10(Predicted)

color 

white

CAS DataBase Reference

4385-77-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

29333990

3-(3-PYRIDINYL)BENZOIC ACID Usage And Synthesis

Chemical Properties

White or off-white solid

Synthesis

Example 163 A Synthesis of 3-(pyridin-3-yl)benzoic acid: 3-Carboxyphenylboronic acid (1.5 g, 9 mmol) and 3-bromopyridine (1.5 g, 9.9 mmol) were dissolved in a solvent mixture of acetonitrile (40 mL) and water (40 mL). Potassium carbonate (5.5 g, 40 mmol) and bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) were subsequently added. The reaction mixture was stirred under reflux conditions overnight. Upon completion of the reaction, the suspension was filtered while hot and the filtrate was concentrated to half the original volume. The concentrated aqueous phase was washed with dichloromethane. Subsequently, the aqueous phase was adjusted to pH=3 with 1 M hydrochloric acid, the precipitated solid was filtered and washed with water. Finally, the solid residue was dried under vacuum to give 1.5 g of 3-(pyridin-3-yl)benzoic acid in 83% yield.LC-MS (ESI) m/z: 200 (M + 1)+.

References

[1] Synlett, 2000, # 6, p. 829 - 831
[2] Patent: US2009/197863, 2009, A1. Location in patent: Page/Page column 76
[3] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1853 - 1863
[4] Patent: JP5743418, 2015, B2. Location in patent: Paragraph 0142; 0143; 0144

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