5-Nitro-2-phenylbenzofuran

Base Information

• Chemical Name: 5-Nitro-2-phenylbenzofuran
• CAS No.: 16237-97-1
• Molecular Formula: C14H9NO3
• Molecular Weight: 239.23
• DSSTox Substance ID: DTXSID40457650
• Nikkaji Number: J1.835.179J
• Wikidata: Q82280576
• Mol file: 16237-97-1.mol

Synonyms:5-Nitro-2-phenylbenzofuran;16237-97-1;2-phenyl-5-nitrobenzofuran;5-Nitro-2-phenyl benzofuran;SCHEMBL2242477;DTXSID40457650;LSIZJYOZWTXNCL-UHFFFAOYSA-N

Chemical Property of 5-Nitro-2-phenylbenzofuran

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.058243149
• Heavy Atom Count: 18
• Complexity: 309

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=C(O2)C=CC(=C3)[N+](=O)[O-]

Technology Process of 5-Nitro-2-phenylbenzofuran

There total 32 articles about 5-Nitro-2-phenylbenzofuran 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: 92.0%

(Z)-1-((2-bromo-1-phenylvinyl)oxy)-4-nitrobenzene → 5-nitro-2-phenylbenzofuran (16237-97-1)

Guidance literature:

With potassium carbonate; palladium dichloride; In N,N-dimethyl-formamide; at 130 ℃; for 6h; under air; sealed tube;

DOI:10.1021/ol202383z

Reference yield: 92.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → 5-nitro-2-phenylbenzofuran (16237-97-1)

Guidance literature:

With 1,10-Phenanthroline; copper(II) acetate hydrate; sodium acetate; palladium diacetate; In 1,2-dichloro-ethane; at 110 ℃; for 24h; Reagent/catalyst; Solvent; Concentration; Kinetics; Molecular sieve;

DOI:10.1002/anie.201305326

Reference yield: 88.0%

2-iodo-4-nitrophenol (89487-91-2) + phenylacetylene (536-74-3) → 5-nitro-2-phenylbenzofuran (16237-97-1)

Guidance literature:

With dichloro{2-[(1H-pyrazol-1-yl-κN²)methyl]-6-(1H-pyrazol-1-yl-κN²)pyridine-κN}copper(II); caesium carbonate; In 1,4-dioxane; at 130 ℃; for 72h; Sealed tube; Inert atmosphere;

DOI:10.1002/adsc.201301010

upstream raw materials:

2'-hydroxy-5'-nitro-deoxybenzoin

sulfuric acid

acetic acid

2-iodo-4-nitrophenol

Downstream raw materials:

2-phenylbenzofuran-5-amine

Refernces

• 1、 Delogu, Giovanna L.,Kumar, Amit,Gatto, Gianluca,Bustelo, Fernando,Saavedra, Lucía M.,Rodríguez-Franco, Maria Isabel,Laguna, Reyes,Vi?a, Dolores. "Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human monoamine oxidase inhibitors". . . Retrieved 2021/01/14.
• 2、 Borges, Fernanda,Delogu, Giovanna L.,Era, Benedetta,Fais, Antonella,Gatto, Gianluca,Kumar, Amit,Matos, Maria J.,Pintus, Francesca,Uriarte, Eugenio. "Looking for new xanthine oxidase inhibitors: 3-Phenylcoumarins versus 2-phenylbenzofurans". . p. 774 - 780. Retrieved 2020/07/07.