Phenyl 3,5-dinitrobenzoate

Base Information

• Chemical Name: Phenyl 3,5-dinitrobenzoate
• CAS No.: 1523-20-2
• Molecular Formula: C13H8N2O6
• Molecular Weight: 288.216
• DSSTox Substance ID: DTXSID10429228
• Nikkaji Number: J1.775.693A
• Wikidata: Q82242206
• ChEMBL ID: CHEMBL3238208
• Mol file: 1523-20-2.mol

Synonyms:phenyl 3,5-dinitrobenzoate;1523-20-2;Benzoic acid, 3,5-dinitro-, phenyl ester;CHEMBL3238208;3,5-Dinitrobenzoic acid phenyl ester;DTXSID10429228;BDBM50004431

Chemical Property of Phenyl 3,5-dinitrobenzoate

Chemical Property:

• PSA: 117.94000
• LogP: 3.76860
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 288.03823598
• Heavy Atom Count: 21
• Complexity: 388

Purity/Quality:

95% ^*data from raw suppliers

3,5-DINITRO-BENZOIC ACID PHENYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC(=O)C2=CC(=CC(=C2)[N+](=O)[O-])[N+](=O)[O-]

Technology Process of Phenyl 3,5-dinitrobenzoate

There total 11 articles about Phenyl 3,5-dinitrobenzoate 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: 42.0%

3,5-dinitrobenzoic acid (99-34-3) + phenol (108-95-2,27073-41-2) → phenyl 3,5-dinitrobenzoate (1523-20-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1016/j.bmc.2014.03.008

Reference yield: 40.0%

Diphenyliodonium triflate (66003-76-7) + 2,4-dinitrobenzoic acid (610-30-0) → phenyl 3,5-dinitrobenzoate (1523-20-2) + 1,3-dinitro-9H-fluoren-9-one

Guidance literature:

With palladium diacetate; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 ℃; Schlenk technique;

DOI:10.1021/acs.orglett.1c03016

Reference yield:

phenol (108-95-2,27073-41-2) + 3,5-dinitrobenoyl chloride (99-33-2) → phenyl 3,5-dinitrobenzoate (1523-20-2)

Guidance literature:

With pyridine;

DOI:10.1021/ja01356a047

upstream raw materials:

3,5-dinitrobenzoic acid

phenol

3,5-dinitrobenoyl chloride

sodium phenoxide

Downstream raw materials:

3,5-dinitrobenzoic acid

phenolate

Refernces

• 1、 An, Guoqiang,Wang, Limin,Han, Jianwei. "Palladium Catalyzed Regioselective Cyclization of Arylcarboxylic Acids via Radical Intermediates with Diaryliodonium Salts". supporting information. p. 8688 - 8693. Retrieved 2021/11/24.
• 2、 El Seoud, Omar A.,Ruasse, Marie-Francoise,Rodrigues, Wagner A.. "Kinetics and mechanism of phosphate-catalyzed hydrolysis of benzoate esters: Comparison with nucleophilic catalysis by imidazole and o-iodosobenzoate". . p. 1053 - 1058. Retrieved 2007/10/03.