4-(Benzylaminocarbonyl)benzeneboronic acid pinacol ester

Base Information

• Chemical Name: 4-(Benzylaminocarbonyl)benzeneboronic acid pinacol ester
• CAS No.: 1073353-57-7
• Molecular Formula: C20H26BNO4
• Molecular Weight: 337.226
• Hs Code.: 2934999090
• Mol file: 1073353-57-7.mol

Synonyms:4-(Benzylaminocarbonyl)benzeneboronic acid pinacol ester;4-(N-BENZYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER;N-BENZYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZAMIDE;4-(N-Benzylaminocarbonyl)phenylboronic acid,pinacol;[4-(Benzylamino-1-carbonyl)phenyl]boronic acid pinacol ester

Chemical Property of 4-(Benzylaminocarbonyl)benzeneboronic acid pinacol ester

Chemical Property:

• Melting Point: 109-113°C
• PSA: 47.56000
• LogP: 3.30670
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

4-(N-Benzylaminocarbonyl)phenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-(Benzylaminocarbonyl)benzeneboronic acid pinacol ester

There total 5 articles about 4-(Benzylaminocarbonyl)benzeneboronic 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: 88.0%

benzylamine (100-46-9) + 4-carboxyphenylboronic acid pinacol ester (180516-87-4) → N-benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1073353-57-7)

Guidance literature:

With benzotriazol-1-ol; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.06.032

Reference yield: 85.0%

bis(pinacol)diborane (73183-34-3) → N-benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1073353-57-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

DOI:10.1002/anie.201907366

Reference yield: 65.0%

N-benzylbenzamide (1485-70-7) + bis(pinacol)diborane (73183-34-3) → N-benzyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1048647-68-2) + N-benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1073353-57-7) + N-benzyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N-(2,3-dimethyl-1H-indol-7-yl)-[2,2'-bipyridine]-5-carboxamide; In tetrahydrofuran; at 50 - 60 ℃; regioselective reaction; Catalytic behavior; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201907366

upstream raw materials:

4-carboxyphenylboronic acid

benzylamine

4-carboxyphenylboronic acid pinacol ester

benzoic acid

Downstream raw materials:

N-benzyl-4-[4-bromo-2-(2-methoxy-ethoxymethoxy)-5-oxo-2,5-dihydro-furan-3-yl]-benzamide

N-benzyl-4-(4-bromo-2-hydroxy-5-oxo-2,5-dihydro-furan-3-yl)-benzamide

Refernces

• 1、 Morera, Enrico,Di Marzo, Vincenzo,Monti, Ludovica,Allarà, Marco,Schiano Moriello, Aniello,Nalli, Marianna,Ortar, Giorgio,De Petrocellis, Luciano. "Arylboronic acids as dual-action FAAH and TRPV1 ligands". . p. 1401 - 1405. Retrieved 2016/02/19.