3-Cyanophenylboronic acid Chemical Properties

Melting point:

298 °C (dec.) (lit.)

Boiling point:

347.4±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

7.17±0.10(Predicted)

form 

solid

color 

White to Light yellow

BRN 

6136720

InChI

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

InChIKey

XDBHWPLGGBLUHH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

150255-96-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C,Xn

Risk Statements 

36/37/38-34-36-41-37/38-22

Safety Statements 

26-37/39-45-36/37/39-22-39-36

RIDADR 

UN3439

WGK Germany 

3

Hazard Note 

Harmful/Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29163990

MSDS

• Language:English Provider:3-Cyanophenylboronic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Cyanophenylboronic acid Usage And Synthesis

Chemical Properties

light orange powder

Uses

suzuki reaction

Uses

3-Cyanophenylboronic acid can be used:

• As an intermediate in the synthesis of piperidine-based MCH R1 antagonists.
• As a substrate in the Suzuki coupling reactions to prepare 4-aryl-1,8-naphthyridin-2(1H)-ones.
• As an intermediate in the synthesis of biaryl-based?phenylalanine?amino acid analogs, which are used as kainate receptors ligands.
• To prepare phenylimidazole-based?Ir(III) complexes for phosphorescent blue OLED applications.

Synthesis

The general procedure for the synthesis of 3-cyanophenylboronic acid from triisopropyl borate and m-bromobenzonitrile was as follows: 20 g of 3-bromobenzonitrile was dissolved in 100 ml of anhydrous tetrahydrofuran (THF) and mixed with 37.6 ml of triisopropoxyborane under nitrogen protection. The reaction system was cooled to -78 °C, followed by the slow dropwise addition of 98.3 ml of 1.6 M n-butyllithium hexane solution under stirring for about 30 minutes. The reaction mixture was continued to be stirred at room temperature for 30 minutes, then cooled to 0°C and 220 ml of 4M sulfuric acid solution was added. The reaction solution was heated to reflux overnight, cooled again to 0°C, and 340 ml of 5M aqueous sodium hydroxide solution was added, followed by extraction with 200 ml of diethyl ether. The aqueous phase was separated and the pH was adjusted to 2 with 6 M hydrochloric acid and extracted twice with 300 ml ethyl acetate. The ethyl acetate layers were combined, dried with anhydrous magnesium sulfate (MgSO4) and the solvent was removed by distillation under reduced pressure. The resulting crude product was recrystallized by DMF-water system to give 11.6 g (72% yield) of 3-cyanophenylboronic acid as light yellow needle-like crystals. The product was characterized by 1H NMR (270 MHz, DMSO-d6): δ 8.5 (brs, 2H), 8.3-7.6 (m, 4H).

References

[1] Patent: EP1179527, 2002, A1. Location in patent: Page 19-20
[2] Patent: US6348478, 2002, B1. Location in patent: Page column 14
[3] Patent: US2012/295874, 2012, A1. Location in patent: Page/Page column 207
[4] Patent: US2002/45613, 2002, A1
[5] Patent: US6538137, 2003, B1

3-Cyanophenylboronic acid(150255-96-2)Related Product Information

• Methylene dithiocyanate
• Phenylboronic acid
• Methyl 4-cyanobenzoate
• 4-Hydroxyphenylboronic acid
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 4-Tolylboronic acid
• 3,5-Dimethylphenylboronic acid
• Citric acid
• Ascoric Acid
• 3-AMINO-5-CYANOBENZENEBORONIC ACID HYDROCHLORIDE 97
• Boronic acid, (3-cyano-5-fluorophenyl)- (9CI)
• 3-Cyano-4-fluorobenzeneboronic acid
• 2-CHLORO-5-CYANOPHENYLBORONIC ACID
• 5-CYANO-2-FLUOROBENZENEBORONIC ACID
• 2-CYANOPHENYLBORONIC ACID,2-Cyanophenylboronic acid, >90%
• 3-AMINO-5-CYANOPHENYLBORONIC ACID
• 3-CYANO-5-NITROBENZENEBORONIC ACID 98