2-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER Chemical Properties

Melting point:

105-106℃

Boiling point:

370.7±27.0 °C(Predicted)

Density 

1.10

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

-0.33±0.12(Predicted)

color 

White to Light yellow to Light orange

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

741709-63-7

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

HS Code 

2933399990

2-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER Usage And Synthesis

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. It is used in suzuki reactions.

Synthesis

To a 250 mL round bottom flask was added 5-bromo-2-cyanopyridine (3.0 g, 16.39 mmol), bis(pinacolato)diboron (4.58 g, 18.03 mmol), potassium acetate (5.47 g, 55.74 mmol), and dimethyl sulfoxide (100 mL). After degassing for 20 min, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (1.39 g, 1.64 mmol) was added. The reaction mixture was stirred at 80 °C for 24 h, followed by continued stirring at room temperature for 3 days. Upon completion of the reaction, 50 mL of water was added and the product was extracted with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The dark residue was purified by fast column chromatography (eluent: 20% acetone/hexane) to give a red solid. The solid was ground with hexane to give 1.72 g (46% yield) of the target product 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyanopyridine as a light pink solid.

References

[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5473 - 5494
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1277 - 1281
[3] Patent: US2009/136473, 2009, A1. Location in patent: Page/Page column 36; 61
[4] Patent: US2014/364414, 2014, A1. Location in patent: Paragraph 0438; 0449-0450
[5] Patent: WO2009/74812, 2009, A1. Location in patent: Page/Page column 70

2-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER(741709-63-7)Related Product Information

• (2-sulfanylphenyl)boronic acid
• 2-chloro-5-cyanopyridine
• Pyridine
• 3-Pyridylboronic acid
• 2-Aminopyridine-5-boronic acid, pinacol ester
• Indole-4-boronic acid pinacol ester
• 5-AMINOPYRIDINE-3-BORONIC ACID, PINACOL ESTER
• Pinacol
• 2-Chloro-3-cyanopyridine-4-boronic Acid Pinacol Ester
• 3-Cyanopyridine-4-boronic acid pinacol ester, tech. 90%
• 2-CYANOPYRIDINE-3-BORONIC ACID, PINACOL ESTER
• 4-CYANOPYRIDINE-3-BORONIC ACID, PINACOL ESTER,4-Cyanopyridine-3-boronic acid pinacol ester, tech. 90%
• 4-CYANOPYRIDINE-2-BORONIC ACID PINACOL ESTER
• 3-CYANOPYRIDINE-2-BORONIC ACID PINACOL ESTER
• 6-CYANOPYRIDINE-2-BORONIC ACID PINACOL ESTER
• 5-CYANOPYRIDINE-2-BORONIC ACID PINACOL ESTER
• 2-CYANOPYRIDINE-4-BORONIC ACID PINACOL ESTER
• 3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER