3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER Chemical Properties

Melting point:

75-76℃

Boiling point:

334.5±32.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Solid

color 

White to Almost white

Safety Information

RIDADR 

UN3439

HazardClass 

6.1

HS Code 

2931900090

3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER Usage And Synthesis

Synthesis

2-Fluoro-5-bromobenzonitrile (1000.00 mg, 5.00 mmol, 1.00 eq.) and pinacol ester of bisboronic acid (1396.61 mg, 5.50 mmol, 1.10 eq.) were added to potassium acetate (1472.07 mg, 15.00 mmol, 3.00 eq.) in a dioxane (10 mL) and DMF (1 mL) ) in a solvent mixture of dioxane (10 mL) and DMF (1 mL) for degassing. Subsequently, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride 1:1 complex with dichloromethane (366.85 mg, 0.50 mmol, 0.10 eq.) was added. The reaction mixture was placed in a sealed vial and the reaction was heated at 100 °C overnight. After completion of the reaction, it was cooled to room temperature and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, gradient 0 to 5%) to afford the target product 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.0 g, 81% yield).

References

[1] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 0504; 0505; 0506
[2] Patent: WO2011/25799, 2011, A1. Location in patent: Page/Page column 50
[3] Organic Letters, 2004, vol. 6, # 19, p. 3265 - 3268

3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER(775351-57-0)Related Product Information

• 3-Cyanophenylboronic acid
• 3-Cyano-4-fluorobenzeneboronic acid
• 2-FLUORO-5-METHYLPHENYLBORONIC ACID
• 5-CYANO-2-FLUOROBENZENEBORONIC ACID
• 4-Fluorobenzonitrile
• 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FLUOROBENZENE
• 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• 3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER
• 4-Fluoro-3-methylphenylboronic acid
• 2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER