3-Anilinobenzoic acid methyl ester

Base Information

• Chemical Name: 3-Anilinobenzoic acid methyl ester
• CAS No.: 55622-43-0
• Molecular Formula: C14H13NO2
• Molecular Weight: 227.263
• Mol file: 55622-43-0.mol

Synonyms:3-Anilino-benzoesaeure-methylester;methyl 3-anilinobenzoate;m-Diphenylamincarbonsaeuremethylester;3-anilino-benzoic acid methyl ester;methyl 3-phenylaminobenzoate;methyl 3-(phenylamino)benzoate;

Chemical Property of 3-Anilinobenzoic acid methyl ester

Chemical Property:

• PSA: 38.33000
• LogP: 3.28980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Anilinobenzoic acid methyl ester

There total 11 articles about 3-Anilinobenzoic acid methyl 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: 94.0%

methyl 3-bromobenzoate (618-89-3) + aniline (62-53-3) → 3-phenylamino benzoic acid methyl ester (55622-43-0)

Guidance literature:

With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 120 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.01.010

Reference yield: 92.0%

methyl 3-nitrosobenzoate (26960-97-4) + phenylboronic acid (98-80-6) → 3-phenylamino benzoic acid methyl ester (55622-43-0)

Guidance literature:

With triethyl phosphite; In toluene; at 20 ℃; for 0.75h;

DOI:10.1021/acs.orglett.8b00473

Reference yield: 87.0%

aniline (62-53-3) + [3-(methoxycarbonyl)phenyl]boronic acid (99769-19-4) → 3-phenylamino benzoic acid methyl ester (55622-43-0)

Guidance literature:

With (1,3-bis(2,6-diisopropyl-4-((E)-3-methoxy-3-oxoprop-1-en-1-yl)phenyl)-2,3-dihydro-1H-imidazole-2-yl)copper(I) chloride; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2020.131861

upstream raw materials:

m-bromobenzoic acid

aniline

methyl 3-chlorobenzoate

diphenylamine-2-carboxylic acid

Downstream raw materials:

diphenylamine-2-carboxylic acid

N-[3-hydroxymethylphenyl]-N-phenylamine

Refernces

• 1、 Higgins, Clare L.,Filip, Sorin V.,Afsar, Ashfaq,Hayes, Wayne. "Increasing the antioxidant capability via the synergistic effect of coupling diphenylamine with sterically hindered phenol". supporting information. . Retrieved 2019/11/28.
• 2、 Roscales, Silvia,Csák?, Aurelio G.. "Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling". supporting information. p. 1667 - 1671. Retrieved 2018/03/23.