5-CYANO-2-FLUOROBENZENEBORONIC ACID

5-CYANO-2-FLUOROBENZENEBORONIC ACID Property

Melting point:

300

Boiling point:

351.3±52.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

6.97±0.58(Predicted)

color 

White

CAS DataBase Reference

468718-30-1(CAS DataBase Reference)

Safety

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39-22

RIDADR 

3439

Hazard Note 

Harmful/Keep Cold

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

5-CYANO-2-FLUOROBENZENEBORONIC ACID Chemical Properties,Usage,Production

Uses

suzuki reaction

Synthesis

Example 163 Synthesis of 3-(2-dimethylaminomethyl-cyclopropyl)-1H-indazole-5-carbonitrile Procedure: n-BuLi (1.9 M, 26.3 mL, 50 mmol) was slowly added dropwise under nitrogen protection to a solution of diisopropylamine (7.71 mL, 55 mmol) in anhydrous THF (100 mL), keeping the reaction temperature at 0 °C. After 10 min. the reaction system was cooled to -78 °C. Subsequently, a solution of 4-fluorobenzonitrile (6.06 g, 50 mmol) in anhydrous THF (20 mL) was added dropwise at a rate that maintained the internal temperature at -78 °C. After stirring at this temperature for 1 hour, trimethyl borate (8.41 mL, 75 mmol) was added dropwise, also at a rate maintaining an internal temperature of -78 °C. The reaction mixture was stirred at -78 °C and gradually warmed to room temperature for 16 hours. Upon completion of the reaction, the system was cooled to 10 °C and 25 mL of 6N HCl was added. stirring was continued at room temperature for 4 h. The reaction mixture was then partitioned between water and ethyl acetate. The organic layer was washed three times with 100 mL of 2N NaOH. The aqueous layers were combined and adjusted to pH 6 with 6N HCl. The white solid formed was extracted through three times with 100mL ethyl acetate. The organic layers were combined, dried with sodium sulfate, concentrated and dried under high vacuum to give 2-fluoro-5-cyanophenylboronic acid (5.74 g, 70% yield). The product was confirmed by 1H NMR (500 MHz, acetone-d6): δ 8.08 (1H, dd, J = 2.14,5.5 Hz), 7.90 (1H, m), 7.31 (1H, t, J = 8.85 Hz). Elemental analysis (C7H5BFNO2) Calculated values: C, 50.97; H, 3.05; N, 8.49. Measured values: C, 51.19; H, 3.19; N, 8.26.

References

[1] Patent: US2003/73849, 2003, A1