4-Phenoxybenzoic acid

Base Information

• Chemical Name: 4-Phenoxybenzoic acid
• CAS No.: 2215-77-2
• Molecular Formula: C13H10O3
• Molecular Weight: 214.221
• Hs Code.: 29189900
• European Community (EC) Number: 218-682-5
• NSC Number: 246039
• UNII: K7YP1JL5BZ
• DSSTox Substance ID: DTXSID6062258
• Nikkaji Number: J80.430D
• Wikidata: Q27140032
• Metabolomics Workbench ID: 66030
• ChEMBL ID: CHEMBL107518
• Mol file: 2215-77-2.mol

Synonyms:4-carboxy biphenylether;4-carboxybiphenyl ether;4-carboxybiphenyl ether, sodium salt;4-carboxydiphenyl ether;4-phenoxybenzoic acid;4CBPE

Chemical Property of 4-Phenoxybenzoic acid

Chemical Property:

• Appearance/Colour: white to slightly yellow crystalline powder
• Vapor Pressure: 6.07E-06mmHg at 25°C
• Melting Point: 163-165 °C(lit.)
• Refractive Index: 1.5090 (estimate)
• Boiling Point: 364.2 °C at 760 mmHg
• PKA: 4.57(at 25℃)
• Flash Point: 141.7 °C
• PSA: 46.53000
• Density: 1.241 g/cm³
• LogP: 3.17710
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: Very faint turbidity in hot methanol.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.062994177
• Heavy Atom Count: 16
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

4-Phenoxybenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37/39-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=C(C=C2)C(=O)O
• Uses: 4-Phenoxybenzoic acid can block DNA binding of the human papillomarvirus (HPV) E2 protein. It is employed as an intermediate of Sitafloxacin, which is a fluoroquinolone antibiotic that shows promise in the treatment of Buruli ulcer.

Technology Process of 4-Phenoxybenzoic acid

There total 62 articles about 4-Phenoxybenzoic acid 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: 96.0%

4-phenoxybenzonitrile (3096-81-9) → 4-Phenoxybenzoic acid (2215-77-2)

Guidance literature:

With dihydrogen peroxide; potassium hydroxide; In methanol; ethanol; for 4.5h; Reflux;

DOI:10.1002/cmdc.201600327

Reference yield: 95.0%

carbon monoxide (201230-82-2) + 4-phenoxyanilin (139-59-3) → 4-Phenoxybenzoic acid (2215-77-2)

Guidance literature:

With tert.-butylnitrite; methanesulfonic acid; Ru(2,2'-bipyridine)₃Cl₂·6H₂O; water; In acetonitrile; at 20 ℃; for 16h; Autoclave; Irradiation;

DOI:10.1002/adsc.201800532

Reference yield: 92.0%

para-chlorobenzoic acid (74-11-3) + phenol (108-95-2,27073-41-2) → 4-Phenoxybenzoic acid (2215-77-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 12h;

DOI:10.1002/adsc.201000977

upstream raw materials:

n-butyllithium

4-Bromodiphenyl ether

diethyl ether

4-phenoxyiodobenzene

Downstream raw materials:

2-cyano-3-oxo-3-(4-phenoxy-phenyl)-propionic acid methyl ester

3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl-N-(5-(4-phenoxyphenyl)-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamide

Refernces

• 1、 Arora, Aayushi,Kaushal, Jolly,Kumar, Arun,Nautiyal, Divyanshu,Oswal, Preeti,Singh, Siddhant. "Suzuki?Miyaura coupling and O?arylation reactions catalysed by palladium(II) complexes of bulky ligands bearing naphthalene core, Schiff base functionality and biarylphosphine moiety". . . Retrieved 2022/01/19.
• 2、 Yagci, Semih,Gozelle, Mahmut,Kaya, Selen Gozde,Ozkan, Yesim,Aksel, Ahmet Bugra,Bakar-Ates, Filiz,Dundar, Yasemin,Eren, Gokcen. "Hit-to-lead optimization on aryloxybenzamide derivative virtual screening hit against SIRT". . . Retrieved 2021/01/07.