20927-95-1

Usage

Uses

Used in Pharmaceutical Industry:
Dibenzofuran, 2-nitrois used as a key intermediate in the synthesis of conformationally constrained haptens. These haptens are essential for the development of vaccines and drugs targeting specific diseases by enhancing the immune response.
Used in Antiviral Applications:
Dibenzofuran, 2-nitrois also a potential anti-HIV-1 agent, showing promise in the development of new treatments for HIV-1 infection. Its specific mode of action and effectiveness against the virus are areas of ongoing research and development.

InChI:InChI=1/C12H7NO3/c14-13(15)8-5-6-12-10(7-8)9-3-1-2-4-11(9)16-12/h1-7H

Upstream product

• 132-64-9 dibenzofuran 
• 5917-19-1 2-Nitro-6-amino-dibenzofuran 
• 104-82-5 4-Methylbenzyl chloride 
• 620-88-2 4-nitrophenyl phenyl ether 
• 86607-76-3 1-bromo-2-(4-nitrophenoxy)benzene 
• 83486-51-5 1-(5-Nitro-biphenyl-2-yloxy)-pyrrolidine-2,5-dione 
• 83486-48-0 4-methoxy-1-(4-nitro-2-phenylphenoxy)-pyridinium tetrafluoroborate 
• 106961-17-5 2',5'-Dinitro-biphenyl-2-ol 
• 509-14-8 tetranitromethane 
• 35535-82-1 sodium salt of 2-bromophenol 
• 350-46-9 4-Fluoronitrobenzene 
• 95-56-7 2-hydroxybromobenzene 
• 65103-30-2 4-nitrophenyl 2-(allyloxy)benzoate 
• 629-50-5 Tridecane 

Downstream Products

• 144280-50-2 2,8-dinitrodibenzofuran 
• 3693-22-9 dibenzo[b,d]furan-2-amine 
• 51230-49-0 2-chlorodibenzofuran 
• 1426925-57-6 C₄₈H₃₄N₂O₂Si₂ 

Relevant academic research and scientific papers

Double functionalization of 2-amino-2′-hydroxy-1,1′-biaryls: Synthesis of 4-nitro-dibenzofurans and benzofuro-indoles

Several substituted 2′-amino-biphenyl-2-ols were synthesized. The mild and TM-free double functionalization: nitration and cycloetherification of 2′-amino-biphenyl-2-ols have been achieved for the synthesis of functionalized 4-nitro-dibenzofurans utilizing NaNO2 in TFA and water. Interestingly, nitration of phenol ring was observed along with the dibenzofuran ring formation in the one-pot synthesis. The position of the nitro group in several dibenzofurans is also established by X-ray crystal structure studies. Further functionalization of the obtained 4-nitro-dibenzofurans has been carried into 3-nitro-terphenyl-2-ol, novel benzofuro-indoles, and amino-dibenzofurans. The mechanistic understanding on double functionalization of 2′-amino-biphenyl-2-ols suggests that reaction proceeds by a combination of nitration of the phenol ring followed by Sandmeyer reaction for dibenzofuran ring formation.

Regioselective Preparation of 2- and 3-Nitrodibenzofurans by the Direct Nitration of Dibenzofuran

Nitration of dibenzofuran with nitric acid in trifluoroacetic acid gave 3-nitrodibenzofuran selectively under very mild conditions.In contrary, the Friedel-Crafts type nitration using alkyl nitrates and aluminium chloride in nitromethane gave 2-nitrodibenzofuran as the main product.

Quinoline Ligands Improve the Classic Direct C?H Functionalisation/Intramolecular Cyclisation of Diaryl Ethers to Dibenzofurans

The C?H functionalisation approach to the synthesis of dibenzofurans is hampered by a number of problems. Herein we describe the evolution of a cheap, bench stable quinoline ligand, which obviates most of the current limitations and allows for a high yielding synthesis of a range of valuable dibenzofurans. Dibenzofurans are important motifs in natural products and compounds with wide biological activity.

Synthesis of Dibenzofurans by Cu-Catalyzed Deborylative Ring Contraction of Dibenzoxaborins

An efficient transformation of dibenzoxaborins to dibenzofurans by deborylative ring contraction was achieved under mild conditions using a copper catalyst. The method showed a broad substrate scope enabling the preparation of various dibenzofurans, including those bearing a functional group. The ready availability of various dibenzoxaborins enhances the utility of this method, as demonstrated by the regiodivergent synthesis of dibenzofurans.

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.

NOVEL OXIME ESTER COMPOUND AND PHOTORESIST COMPOSITION CONTAINING THE SAME

The present invention relate to an oxime ester compound represented by chemical formula A, and to a photoresist composition containing the same. The X, R1, R2 and R5 of the formula A are as described in the description of the invention. The present inventnion aims to provide the oxime ester compound as a novel photoinitiator which can be used as a photoresist composition.COPYRIGHT KIPO 2018

Microwave-Promoted Pd-Catalyzed Synthesis of Dibenzofurans from Ortho-Arylphenols

ortho-Aryl phenols, synthesized via protecting group free Suzuki–Miyaura coupling of ortho-halophenols and arene boronic acids, undergo a cyclization to dibenzofurans via oxidative C–H activation. The reaction proceeds under microwave irradiation in short reaction times using catalytic amounts of Pd(OAc)2 without additional ligands.

One-Pot Assembly of Fused Heterocycles via Oxidative Palladium-Catalyzed Cyclization of Arylols and Iodoarenes

A one-pot, two-step cyclization reaction of iodoarenes with diversified arylols, including 4-hydroxyquinoline, quinolinone, 4-hydroxypyridine and phenol, has been developed. By using this palladium-catalyzed formal tandem O-arylation, dehydrogenative cross-coupling reaction, a variety of biologically significant fused benzo[4,5]furo heterocycles and dibenzofurans were quickly assembled in high yields with excellent regioselectivity. Notably, the efficient one-pot reaction led to the heterocycles via sequential oxidation, iodination, isomerization and cyclization steps without purification of any reaction intermediates.

Synthesis of Dibenzofurans via C-H Activation of o-Iodo Diaryl Ethers

An efficient method for the synthesis of dibenzofuran from o-iododiaryl ether using reusable Pd/C under ligand-free conditions has been developed. Synthesis of o-iododiaryl ether was achieved in one pot through sequential iodination and O-arylation of phenol under mild reaction conditions.

One pot synthesis of diarylfurans from aryl esters and PhI(OAc)2 via palladium-associated iodonium ylides

The example of palladium-catalyzed intermolecular cyclization for the synthesis of various diarylfurans in which one of the aromatic rings originates from the phenolic part of the starting ester and the other one from PhI(OAc)2 has been reported. The reaction is carried out through two steps: the rearrangement of palladium-associated iodonium ylides to form o-iodo diaryl ether and then palladium catalyzed intramolecular direct arylation. This reaction can tolerate a variety of functional groups and is alternative or complementary to the previous methods for the synthesis of diarylfurans.