2-METHYL-5-CYANOPHENYL BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2-METHYL-5-CYANOPHENYL BORONIC ACID PINACOL ESTER
• CAS No.: 863868-32-0
• Molecular Formula: C14H18 B N O2
• Molecular Weight: 243.113
• Hs Code.: 2934999090
• Mol file: 863868-32-0.mol

Synonyms:2-Methyl-5-cyanophenyl boronic acid pinacol ester;B-4655;

Chemical Property of 2-METHYL-5-CYANOPHENYL BORONIC ACID PINACOL ESTER

Chemical Property:

• PSA: 42.25000
• LogP: 2.16588
• Storage Temp.: Room temperature.

Purity/Quality:

95% ^*data from raw suppliers

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-METHYL-5-CYANOPHENYL BORONIC ACID PINACOL ESTER

There total 4 articles about 2-METHYL-5-CYANOPHENYL BORONIC ACID PINACOL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-bromo-4-methyl-benzonitrile (42872-74-2) + bis(pinacol)diborane (73183-34-3) → 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (863868-32-0)

Guidance literature:

With potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80 ℃; for 3h; Microwave irradiation;

Reference yield:

3-chloro-4-methylbenzonitrile (21423-81-4) + bis(pinacol)diborane (73183-34-3) → 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (863868-32-0)

Guidance literature:

With caesium carbonate; [2-[(dimethylamino-κN)methyl]phenyl-κC](tricyclohexylphosphine)(trifluoroacetato-κO-(SP-4-3)palladium); In 1,4-dioxane; for 4h; Heating / reflux;

Reference yield:

para-methylbenzonitrile (104-85-8) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (863868-32-0) + 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (863868-22-8)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 25 ℃; for 72h; Title compound not separated from byproducts;

DOI:10.1021/ja0428309

upstream raw materials:

para-methylbenzonitrile

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

3-chloro-4-methylbenzonitrile

bis(pinacol)diborane

Downstream raw materials:

3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-methylbenzonitrile

Refernces

• 1、 -. "POSITIVE ALLOSTERIC MODULATORS OF MGLUR2". Page/Page column 59. . Retrieved 2012/01/05.
• 2、 Chotana, Ghayoor A.,Rak, Michael A.,Smith, Milton R.. "Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles". . p. 10539 - 10544. Retrieved 2007/10/03.