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

Melting point:

95-99 °C(lit.)

Boiling point:

345.8±25.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Powder

color 

Light yellow to orange or light tan

InChI

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

InChIKey

HOPDTPGXBZCBNP-UHFFFAOYSA-N

SMILES

CC1(C)OB(OC1(C)C)c2ccc(cc2)C#N

CAS DataBase Reference

171364-82-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29319090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

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

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

Chemical Properties

light yellow to orange or light tan crystalline powde

Uses

4-(Cyanophenyl)boronic Acid Pinacol Ester is used to prepare arylparacyclophanes via Suzuki aryl cross-coupling of bromoparacyclophane with arylboronic acid and arylboronates. It’s also used to prepare tyrosine-modified analogs of α4β7 integrin inhibitor biotin-R8ERY.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 7508, 1995 DOI: 10.1021/jo00128a024

Synthesis

Under argon protection, 4-bromobenzonitrile 91.1 g (0.5 mol), sodium acetate 98.4 g (1.2 mol), diethylene glycol dimethyl ether 800 mL and bis(pinacolato)diboron 152.4 g (0.6 mol) were added sequentially, the reaction temperature was controlled at 140 ??C, and catalyst 1,1'-bis(dicyclohexylphosphino)ferrocene palladium chloride 375.5 mg was added (0.5 mmol), the reaction was detected by high performance liquid chromatography (HPLC) after 14 h. The reaction was quenched with 600 mL of water, extracted with 300 mL of toluene for 3 times, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was recovered by decompression to obtain a brown solid, which was distilled using a 4L oil pump to obtain 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolato) benzonitrile 111.4 g. Content 99.5% (GC), yield 97.2%, melting point 93.6-94.5 ??.

4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(171364-82-2)Related Product Information

• 4-Cyanophenylboronic acid
• Tetramethylthiuram Disulfide
• 3,3'-IMINOBIS(N,N-DIMETHYLPROPYLAMINE)
• 1,2,3,4-TETRAMETHYL-1,3-CYCLOPENTADIENE
• Tetramethyl glutaric aciduria
• 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• 4-Cyano-2-fluorobenzeneboronic acid, pinacol ester
• 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)TOLUENE
• 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile