3-Fluoro-4-methylphenylboronic acid Chemical Properties

Melting point:

232-237 °C (lit.)

Boiling point:

278.7±50.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

7.76±0.10(Predicted)

form 

Crystalline Powder

color 

White

BRN 

8544594

CAS DataBase Reference

168267-99-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-25

Safety Statements 

26-36/37/39-45-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Fluoro-4-methylphenylboronic acid Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

Reactant for:• ;Regioselective Suzuki coupling1,2

Uses

suzuki reaction

Uses

3-Fluoro-4-methylphenylboronic acid is an inhibitor of bacterial quorum sensing in Vibrio harveyi.

Synthesis

General procedure for the synthesis of 3-fluoro-4-methylphenylboronic acid from 2-fluoro-4-iodotoluene: In a 50 mL round-bottomed flask (equipped with a side arm, condenser, and stirring bar) triphenylphosphine (0.131 g, 0.5 mmol, 20 mol%), 2-fluoro-4-iodotoluene (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol). The reaction system was degassed by alternating vacuum and argon filling three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol%) was added under positive argon atmosphere. After stirring for 15 minutes at room temperature, diisopropylaminoborane (5 mL, 1 M THF solution, 5 mmol) was added and the reaction mixture was again degassed by alternating vacuum and argon filling three times. The reaction mixture was heated to reflux and kept at reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and methanol (6 mL, note: this is an exothermic reaction accompanied by hydrogen release) was slowly added. After stirring for 15 minutes, all solvent was removed by distillation under reduced pressure to give a black solid. The solid was dissolved in 3M sodium hydroxide solution (8 mL) and washed with hexane (3 x 10 mL). The aqueous phase was cooled to 0°C (ice bath) and acidified with concentrated hydrochloric acid to pH ≤ 1, at which point 3-fluoro-4-methylphenylboronic acid precipitated as a white solid. The aqueous phase was extracted with ether (3 x 10 mL), the organic phases were combined, dried with magnesium sulfate and filtered. The solvent was removed by distillation under reduced pressure to give a white solid product.

References

[1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583

3-Fluoro-4-methylphenylboronic acid(168267-99-0)Related Product Information

• Sodium tetrafluoroborate
• 4-Methoxyphenylboronic acid
• Methylboronic acid
• Phenylboronic acid
• Fluoroboric acid
• 4-Tolylboronic acid
• Phenylmethylsulfonyl fluoride
• 3-(Trifluoromethyl)benzaldehyde
• 3,5-Dimethylphenylboronic acid
• Benzotrifluoride
• 2 3-DIFLUORO-4-FORMYPHENYLBORONIC ACID
• 2-Fluoro-4-biphenylylboronic acid
• 3-FLUORO-4-METHOXYCARBONYLPHENYLBORONIC ACID
• 4-ETHOXYCARBONYL-3-FLUOROPHENYLBORONIC ACID
• 3-Fluoro-4-hydrazinocarbonylphenylboronic acid
• 3-Fluoro-4-formylphenylboronic acid
• 4-Carboxy-3-fluorophenylboronic acid
• Fluorine