4-Cyano-2-Methylphenylboronic acid, pinacol ester

Base Information

• Chemical Name: 4-Cyano-2-Methylphenylboronic acid, pinacol ester
• CAS No.: 848953-05-9
• Molecular Formula: C14H18BNO2
• Molecular Weight: 243.113
• Hs Code.: 2931900090
• Mol file: 848953-05-9.mol

Synonyms:

Chemical Property of 4-Cyano-2-Methylphenylboronic acid, pinacol ester

Chemical Property:

• Boiling Point: 369.6±35.0 °C(Predicted)
• PSA: 42.25000
• Density: 1.05±0.1 g/cm3(Predicted)
• LogP: 2.16588
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

4-Cyano-2-methylphenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Cyano-2-Methylphenylboronic acid, pinacol ester

There total 3 articles about 4-Cyano-2-Methylphenylboronic 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: 89.0%

4-bromo-3-methylbenzonirtile (41963-20-6) + bis(pinacol)diborane (73183-34-3) → 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (848953-05-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 125 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1021/acs.jmedchem.9b00747

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + (4-cyano-2-methylphenyl)boronic acid (313546-18-8) → 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (848953-05-9)

Guidance literature:

With magnesium sulfate; In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.142

Reference yield:

4-bromo-3-methylbenzonirtile (41963-20-6) → 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (848953-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere

1.2: 0.75 h / -98 - 20 °C / Inert atmosphere

2.1: hydrogenchloride; water / tetrahydrofuran / 0.25 h / 20 °C

3.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; water; magnesium sulfate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.09.142

upstream raw materials:

4-bromo-3-methylbenzonirtile

bis(pinacol)diborane

2,3-dimethyl-2,3-butane diol

(4-cyano-2-methylphenyl)boronic acid

Downstream raw materials:

3-(bromomethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

C₂₃H₃₇FN₂O₅

4-(4-bromothiophen-3-yl)-3-methylbenzonitrile

(E)-ethyl 3-(4-(4-cyano-2-methylphenyl)thiophen-3-yl)acrylate