Benzyl 3-aminobenzoate

Base Information

• Chemical Name: Benzyl 3-aminobenzoate
• CAS No.: 80787-43-5
• Molecular Formula: C14H13NO2
• Molecular Weight: 227.263
• European Community (EC) Number: 868-930-7
• DSSTox Substance ID: DTXSID70572683
• Nikkaji Number: J1.156.942K
• Wikidata: Q82461109
• Mol file: 80787-43-5.mol

Synonyms:benzyl 3-aminobenzoate;80787-43-5;Benzoic acid, 3-amino-, phenylmethyl ester;benzyl m-aminobenzoate;benzyl3-aminobenzoate;SCHEMBL913728;DTXSID70572683;3-amino-benzoic acid benzyl ester;YQEQHIZMMDWDOV-UHFFFAOYSA-N;AKOS005158375;SB79649;CS-0258478;EN300-70266;G22538;Z91832576

Chemical Property of Benzyl 3-aminobenzoate

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 227.094628657
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C2=CC(=CC=C2)N

Technology Process of Benzyl 3-aminobenzoate

There total 10 articles about Benzyl 3-aminobenzoate 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: 98.0%

benzyl 3-(tert-butoxycarbonylamino) benzoate (123986-60-7) → 3-aminobenzoic acid benzyl ester (80787-43-5)

Guidance literature:

benzyl 3-(tert-butoxycarbonylamino) benzoate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

With sodium hydrogencarbonate; In dichloromethane; water; Cooling with ice;

DOI:10.1016/j.tet.2011.12.030

Reference yield: 87.0%

meta-aminobenzoic acid (99-05-8,159139-79-4) + benzyl alcohol (100-51-6,185532-71-2) → 3-aminobenzoic acid benzyl ester (80787-43-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; for 5h;

DOI:10.1002/ardp.200700177

Reference yield: 47.0%

benzyl bromide (100-39-0) + meta-aminobenzoic acid (99-05-8,159139-79-4) → 3-aminobenzoic acid benzyl ester (80787-43-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.8b01512

upstream raw materials:

3-nitrobenzoic acid benzyl ester

benzyl 3-(tert-butoxycarbonylamino) benzoate

meta-aminobenzoic acid

3-[(tert-butoxycarbonyl)amino]benzoic acid

Downstream raw materials:

benzyl N-Boc-D,L-m-Tyr(O-Pyrim)-m-aminobenzoate

benzyl N-Boc-Tyr(O-Pyrim)-m-aminobenzoate

3-{[2-(2-adamantan-1-ylethyl)-5-phenyl-1H-pyrrole-3-carbonyl]amino}benzoic acid benzyl ester

3-[(2-cycloheptylmethyl-5-naphthalen-2-yl-1H-pyrrole-3-carbonyl)-amino]-benzoic acid benzyl ester

Refernces

• 1、 Khan, Gul Shahzada,Dickson, Benjamin D.,Barker, David. "Synthesis of benzoic acids and polybenzamides containing tertiary alkylamino functionality". experimental part. p. 1790 - 1801. Retrieved 2012/03/11.
• 2、 Krauss, Juergen,Knorr, Veronika,Manhardt, Vera,Scheffels, Stefanie,Bracher, Franz. "Synthesis of platensimycin analogues and their antibiotic potency". experimental part. p. 386 - 392. Retrieved 2009/04/16.