2-Fluoropyridine-4-boronic acid Chemical Properties

Melting point:

ca 195℃

Boiling point:

326.8±52.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

6.51±0.10(Predicted)

color 

White to Almost white

CAS DataBase Reference

401815-98-3(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37

Hazard Note 

Irritant

HS Code 

29339900

2-Fluoropyridine-4-boronic acid Usage And Synthesis

Chemical Properties

Solid

Uses

2-Fluoropyridine-4-boronic Acid is used to synthesize analogues of the antitubercular drug.

Synthesis

Step 1: 4-bromo-2-fluoropyridine (30.0 g, 0.17 mol) and triisopropyl borate (38.4 g, 0.20 mol) were dissolved in a solvent mixture of anhydrous toluene and tetrahydrofuran (THF) (4:1, 250 mL) under nitrogen protection. The reaction mixture was cooled to -78 °C, followed by slow dropwise addition of n-butyllithium (80 mL, 0.20 mol, 2.5 M hexane solution) over 30 min. After the dropwise addition was completed, stirring was continued at -78 °C for 30 min. The reaction mixture was then slowly warmed up to -20°C over 1 hr. The progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent: petroleum ether (PE):ethyl acetate (EtOAc) = 1:1) to confirm that the raw materials were completely consumed. Upon completion of the reaction, the mixture was acidified to pH 2 with 3N HCl (50 mL) and stirred at room temperature for 15 minutes. The reaction mixture was transferred to a partition funnel and extracted with EtOAc (150 mL) and water (150 mL). The organic layer was separated, washed sequentially with water and brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give (2-fluoropyridin-4-yl)boronic acid (22.0 g, 91% yield) as a white solid.

References

[1] Patent: WO2015/103137, 2015, A1. Location in patent: Paragraph 00178
[2] Patent: US7087755, 2006, B1. Location in patent: Page/Page column 6
[3] Patent: US2004/122237, 2004, A1. Location in patent: Page 201

2-Fluoropyridine-4-boronic acid(401815-98-3)Related Product Information

• Flupirtine
• 4-Bromo-2-fluoropyridine
• 3-Pyridylboronic acid
• 2-Fluoro-4-iodopyridine
• Potassium tetrafluoroborate
• 2-Pyridineboronic acid
• Sodium tetrafluoroborate
• Pyridine-4-boronic acid
• 2-Fluoropyridine
• 2,6-Lutidine
• Fluoroboric acid
• Ammonium fluoborate
• 2-Chloro-3-cyanopyridine
• 5-CHLORO-2-FLUOROPYRIDINE-4-BORONIC ACID
• 3-CHLORO-2-FLUORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE
• 2,6-Difluoropyridine-4-boronic acid
• 2-FLUOROPYRIDINE-4-BORONIC ACID PINACOL ESTER
• 2-FLUOROPYRIDINE-5-BORONIC ACID,6-FLUOROPYRIDINE-3-BORONIC ACID