3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE Chemical Properties

Melting point:

78-82 °C (lit.)

Boiling point:

341.0±25.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

color 

White

InChI

InChI=1S/C13H16BNO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-6-10(8-11)9-15/h5-8H,1-4H3

InChIKey

FIGQEPXOSAFKTA-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1

CAS DataBase Reference

214360-46-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE Usage And Synthesis

Chemical Properties

White solid

Uses

3-Cyanophenylboronic acid pinacol ester can be used as a reactant to synthesize:

• 3-Cyano aryl/ heteroaryl derivatives by forming a C?C bond via palladium-catalyzed Suzuki-Miyaura reaction.
• 3-(Phenylamino)benzonitrile by copper-catalyzed Chan-Evans-Lam amination reaction.
• 3-(Trifluoromethyl)benzonitrile using potassium (trifluoromethyl)trimethoxyborate.

Synthesis

To a solution of 3-aminobenzonitrile (0.5 g, 4.23 mmol) in acetonitrile (30 mL) was added tert-butyl nitrite (0.7 mL, 6.34 mmol) and pinacol ester of bis(boronic acid) (1.29 g, 5.076 mmol) sequentially at 0 °C. The reaction mixture was warmed to 80 °C and stirred continuously for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (combiflash system) with the eluent being a 4% ethyl acetate/hexane solvent mixture, resulting in pinacol ester of 3-cyanobenzeneboronic acid (0.35 g, 99.8% yield). The molecular weight of the product was confirmed by LCMS analysis: m/z 294 ([M+H]+).

References

[1] Patent: WO2015/105779, 2015, A1. Location in patent: Page/Page column 17; 18
[2] Patent: US2016/333005, 2016, A1. Location in patent: Paragraph 0064-0065
[3] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933
[4] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849

3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(214360-46-0)Related Product Information

• 3-Cyanophenylboronic acid
• 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE,4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE 97%
• 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
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• 3-CYANO-4-FLUOROPHENYLBORONIC ACID, PINACOL ESTER
• 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• 1,3-DICYANO-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZENE
• 5-Cyano-2-methoxyphenylboronic acid pinacol ester