3-CYANOPYRIDIN-4-YLBORONIC ACID

3-CYANOPYRIDIN-4-YLBORONIC ACID Property

Boiling point:

407.9±55.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

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

pka

7.04±0.58(Predicted)

Safety

Hazard Codes 

Xn

Risk Statements 

22

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

3-CYANOPYRIDIN-4-YLBORONIC ACID Chemical Properties,Usage,Production

Synthesis

Under nitrogen protection, 300 g of anhydrous tetrahydrofuran was added to the reaction flask with stirring turned on, followed by the addition of 12 g of 3-cyanopyridine and cooling of the system to -30°C. The reaction was carried out under nitrogen protection. Slowly 70 mL of 2.0 M n-butyllithium solution was added dropwise. After stirring for 30 minutes, 1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane solution was added slowly dropwise. After 2 hours of reaction, 41 mL of triisopropyl borate was slowly added dropwise. Stirring was continued at -30°C for 1 hour, then slowly warmed to room temperature and stirred for 1 hour. To the reaction mixture was added 400 g of concentrated hydrochloric acid and stirred for 1 hour for hydrolysis. After completion of the reaction, the reaction was left to partition and the organic layer was washed with water three times (100 g each). The aqueous layer was combined and extracted once with 100 mL of petroleum ether. The organic layers were combined, dried with 50 g of anhydrous sodium sulfate and filtered. The filtrate was concentrated to dryness to give 14 g of 3-cyano-4-pyridineboronic acid.

References

[1] Patent: CN102718785, 2016, B. Location in patent: Paragraph 0040; 0041