N-Methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Base Information

• Chemical Name: N-Methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
• CAS No.: 1073353-58-8
• Molecular Formula: C15H22BNO4
• Molecular Weight: 291.155
• Hs Code.: 2934999090
• Mol file: 1073353-58-8.mol

Synonyms:4-(N-Methoxy-N-methylcarbamoyl)phenylboronic acid pinacol ester;N-Methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide;1-(N-METHOXY-N-METHYLCARBAMOYL)-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE;4-(N,O-DIMETHYLHYDROXYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER;N-Methoxy-N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Chemical Property of N-Methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Chemical Property:

• Melting Point: 94-101 °C
• PSA: 48.00000
• LogP: 1.61920
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid, pinacol ester

Technology Process of N-Methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

There total 3 articles about N-Methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 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:

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 4-carboxyphenylboronic acid pinacol ester (180516-87-4) → N-methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (1073353-58-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

bis(pinacol)diborane (73183-34-3) + 4-bromo-N-methoxy-N-methylbenzamide (192436-83-2) → N-methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (1073353-58-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃;

DOI:10.1016/j.bmcl.2017.06.032

Reference yield:

4-chlorobenzoyl chloride (586-75-4) → N-methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (1073353-58-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 80 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2017.06.032

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

4-carboxyphenylboronic acid pinacol ester

bis(pinacol)diborane

4-bromo-N-methoxy-N-methylbenzamide

Downstream raw materials:

[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl](1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)methanone

2,2-difluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone

ethyl 3-{-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl}-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)acrylate