2-Cyanophenylboronic acid Chemical Properties

Melting point:

240 °C (dec.) (lit.)

Boiling point:

376.4±44.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

pka

7.98±0.58(Predicted)

form 

Powder

color 

Off-white to cream

InChI

InChI=1S/C7H6BNO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,10-11H

InChIKey

NPLZNDDFVCGRAG-UHFFFAOYSA-N

SMILES

B(C1=CC=CC=C1C#N)(O)O

CAS DataBase Reference

138642-62-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39-36

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

MSDS

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

2-Cyanophenylboronic acid Usage And Synthesis

Chemical Properties

off-white to cream powder

Uses

2-Cyanophenylboronic Acid is used in the synthesis of pyridine inhibitors of TAK1. Also participates in the discovery and synthesis of 1,2,4-triazoles as novel allosteric valosine containing protein (VCP) inhibitors. VCP is found highly abundant in various tumor types allowing for a potential target in cancer therapy.

Synthesis

Under nitrogen protection, 7.88 g (55.8 mmol) of 2,2,6,6-tetramethylpiperidine and 2.77 g (65.3 mmol) of lithium chloride (1.17:1 molar ratio to 2,2,6,6-tetramethylpiperidine) in THF were added to a 300 mL flask. A lithium 2,2,6,6-tetramethylpiperidine solution was prepared by slow dropwise addition of 24.2 g (58.2 mmol) of 15% n-butyllithium hexane solution at -10 °C. After cooling the reaction system to -50 °C, 10.93 g (58.2 mmol) of triisopropoxyborane and 4.98 g (48.3 mmol) of benzonitrile were added sequentially dropwise, and the reaction was maintained at this temperature for 3 h. HPLC analysis showed that the area percentage of 2-cyanobenzeneboronic acid in the reaction solution was 98.6%, and the by-product, 1 -phenyl-1 -(2,2,6,6-tetramethylpiperidin- 1-yl)methylimine had an area percentage of 1.38%. The reaction solution was poured into 38 mL of 3N HCl for hydrolysis and 150 mL of ethyl acetate was added for extraction to separate the aqueous phase. The organic phase was washed with 50 mL of 0.2N HCl and quantitatively analyzed by HPLC to confirm that the yield of 2-cyanophenylboronic acid was 95.0% and it contained 0.45% of 1-phenyl-(2,2,6,6-tetramethylpiperidin-1-yl)methylimine.

References

[1] Patent: JP2015/160823, 2015, A. Location in patent: Paragraph 0053

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