Benzyl p-aminobenzoate

Base Information

• Chemical Name: Benzyl p-aminobenzoate
• CAS No.: 19008-43-6
• Molecular Formula: C14H13NO2
• Molecular Weight: 227.263
• Hs Code.: 2922499990
• European Community (EC) Number: 242-741-4
• NSC Number: 30685
• UNII: QY5LYM6X12
• DSSTox Substance ID: DTXSID00172473
• Nikkaji Number: J224.828J
• Wikidata: Q27287557
• Mol file: 19008-43-6.mol

Synonyms:benzyl 4-aminobenzoate;Benzyl p-aminobenzoate;19008-43-6;4-Aminobenzoic acid benzyl ester;UNII-QY5LYM6X12;QY5LYM6X12;EINECS 242-741-4;NSC-30685;Benzoic acid, 4-amino-, phenylmethyl ester;benzyl4-aminobenzoate;Benzyl-P-aminobenzoate;phenylmethyl 4-aminobenzoate;SCHEMBL1009228;p-aminobenzoic acid benzyl ester;DTXSID00172473;4-Amino-benzoic acid benzyl ester;NSC30685;NSC 30685;AKOS005158398;SB80184;UPCMLD00WDMA007477:001;1-Me-3-(trimEtsilyloxy)-1,3-butadiene;BS-49815;CS-0156252;E76222;J-640287;J-800287;Q27287557

Chemical Property of Benzyl p-aminobenzoate

Chemical Property:

• Vapor Pressure: 5.42E-07mmHg at 25°C
• Melting Point: 84.7 °C
• Refractive Index: 1.618
• Boiling Point: 411.8 °C at 760 mmHg
• PKA: 2.34±0.10(Predicted)
• Flash Point: 242.1 °C
• PSA: 52.32000
• Density: 1.194 g/cm³
• LogP: 3.20700
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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: 241

Purity/Quality:

99% ^*data from raw suppliers

Benzylp-Aminobenzoate ^*data from reagent 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=C(C=C2)N
• Uses: Benzyl p-Aminobenzoate is used in the development of potent and selective plasmin and plasma kallikrein inhibitors. Also used in the synthesis of pyrrolinones as potential therapeutics in the treatment of Niemann-Pick type C disease.

Technology Process of Benzyl p-aminobenzoate

There total 20 articles about Benzyl p-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: 100.0%

benzyl bromide (100-39-0) + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → benzyl 4-aminobenzoate (19008-43-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.6b01478

Reference yield: 97.0%

benzyl 4-nitrobenzoate (14786-27-7) → benzyl 4-aminobenzoate (19008-43-6)

Guidance literature:

With 10% Pd/C; diphenyl sulfide; hydrogen; In methanol; at 20 ℃; for 24h; chemoselective reaction;

DOI:10.1002/adsc.200700571

Reference yield: 96.0%

C14H11N3O2 → benzyl 4-aminobenzoate (19008-43-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 24h; chemoselective reaction;

DOI:10.1002/cctc.201300639

upstream raw materials:

benzyl 4-nitrobenzoate

benzyl 4-((tert-butoxycarbonyl)amino)benzoate

4-nitro-benzoyl chloride

benzyl alcohol

Downstream raw materials:

benzyl 4-{(3R,4R)-3,4-bis(benzyloxy)-2,5-dioxopyrrolidin-1-yl}-benzoate

4-iodobenzoic acid benzyl ester

4-(benzyloxycarbonyl)phenylisocyanide

C₂₇H₂₈N₂O₆

Refernces

• 1、 Bukhari, Shazreh,Cabral, Aaron D.,Gawel, Justyna M.,Gunning, Patrick T.,Israelian, Johan,Manaswiyoungkul, Pimyupa,Nawar, Nabanita,Olaoye, Olasunkanmi O.,Radu, Tudor B.,Raouf, Yasir S.,Sedighi, Abootaleb,Shouksmith, Andrew E.,Sina, Diana,Toutah, Krimo,de Araujo, Elvin D.. "PTG-0861: A novel HDAC6-selective inhibitor as a therapeutic strategy in acute myeloid leukaemia". . . Retrieved 2020/07/03.
• 2、 Motoyama, Yukihiro,Morii, Koshi,Ishizuka, Shoya,Inomoto, Sou,Zhang, Zhenzhong,Yoon, Seong-Ho. "Specific Inhibition of the Hydrogenolysis of Benzylic C?O Bonds Using Palladium Nanoparticles Supported on Nitrogen-Doped Carbon Nanofibers". . p. 505 - 509. Retrieved 2018/02/15.