5-Cyano-2-methoxyphenylboronic acid pinacol ester

Base Information

• Chemical Name: 5-Cyano-2-methoxyphenylboronic acid pinacol ester
• CAS No.: 706820-96-4
• Molecular Formula: C₁₄H₁₈BNO₃
• Molecular Weight: 259.113
• Hs Code.: 2934999090
• Mol file: 706820-96-4.mol

Synonyms:4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile

Chemical Property of 5-Cyano-2-methoxyphenylboronic acid pinacol ester

Chemical Property:

• PSA: 51.48000
• LogP: 1.86608
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

5-Cyano-2-methoxyphenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Cyano-2-methoxyphenylboronic acid pinacol ester

There total 5 articles about 5-Cyano-2-methoxyphenylboronic 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: 92.0%

3-bromo-4-methoxybenzonitrile (117572-79-9) + bis(pinacol)diborane (73183-34-3) → 4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (706820-96-4)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 100 ℃; for 3h; Inert atmosphere;

Reference yield:

4-methoxybenzonitrile (874-90-8) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (706820-96-4) + 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaboryl)benzonitrile (863868-23-9)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 25 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1021/ja0428309

Reference yield:

3-bromo-4-hydroxybenzonitrile (2315-86-8) → 4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (706820-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / acetonitrile / 6 h / 25 °C

2: potassium acetate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere; Reflux

With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate; potassium carbonate; In 1,4-dioxane; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

4-methoxybenzonitrile

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

3-bromo-4-methoxybenzonitrile

bis(pinacol)diborane