13054-95-0

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-diphenyl-1-benzofuran is used as a building block for the synthesis of various organic compounds and pharmaceuticals, leveraging its chemical structure to create new therapeutic agents.
Used in Antioxidant and Anti-inflammatory Applications:
DBF is utilized for its antioxidant and anti-inflammatory properties, potentially offering benefits in the treatment of conditions associated with oxidative stress and inflammation.
Used in Cancer and Neurodegenerative Disease Treatment:
2,3-diphenyl-1-benzofuran is studied for its potential therapeutic use in treating cancer and neurodegenerative diseases, due to its biological activities that may contribute to disease management or mitigation.
Used in Organic Light-Emitting Diodes (OLEDs) and Electronic Devices:
DBF is employed in the development of organic light-emitting diodes and other electronic devices, taking advantage of its unique electronic and photophysical characteristics to enhance device performance.

Upstream product

• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 108-95-2 phenol 
• 6652-29-5 2-phenoxy-1,2-diphenylethanone 
• 4237-46-1 α-phenylbenzoin 
• 33719-60-7 <2-(Benzoyloxy)phenyl>phenylketon 
• 151832-48-3 2-(benzotriazol-1-yl)-2-(o-hydroxyphenyl)-1,1-diphenylethanol 
• 451-40-1 phenyl benzyl ketone 
• 583-53-9 2,3-dibromobenzene 
• 134-81-6 benzil 
• 591-50-4 iodobenzene 
• 92151-73-0 2-phenylethynylphenol 
• 271-89-6 1-benzofurane 
• 108-90-7 chlorobenzene 
• 71-43-2 benzene 

Downstream Products

• 1297374-17-4 C₅₀H₃₂O 
• 1297374-67-4 C₂₆H₂₅BO₃ 
• 55082-66-1 5-bromo-2,3-diphenylbenzofuran 
• 6723-03-1 6-bromo-2,3-diphenyl-benzofuran 
• 194784-78-6 6-iodo-2,3-diphenylbenzo[b]furan 
• 29938-00-9 2,3-diphenyl-benzofuran-7-ol 
• 40112-62-7 3,3-diphenyl-2(3H)-benzofuranone 

Relevant academic research and scientific papers

Synthesis of Conformationally Restricted 2,3-Diarylbenzo[b]furan by the Pd-Catalyzed Annulation of o-Alkynylphenols: Exploring a Combinatorial Approach

The palladium/bpy-catalyzed annulation of o-alkynylphenol with various aryl halides to generate diversified 2,3-diarylbenzo[b]furan is herein described. This method provides an efficient synthetic pathway for the combinatorial synthesis of conformationally restricted 2,3-diarylbenzo[b]furan for drug discovery.

Direct Observation and Reactivities of Benzoyl- and Methoxycarbonyldiphenylmethyl Cations

13C N.m.r. spectra, rates of decomposition, and reaction products are reported for the methoxycarbonyldiphenylmethyl and benzoyldiphenylmethyl cations in ClSO3H-CHCl3.

C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls

The aerobic oxidative coupling of arenes such as benzofuran and N-substituted indoles with benzene and derivatives thereof is described. The reaction is shown to take place in both inter- and intramolecular scenarios.

Palladium-catalyzed cross-coupling of benzyl ketones and α,β- unsaturated carbonyl and phenolic compounds with o-dibromobenzenes to produce cyclic products

A number of carbonyl and phenolic compounds efficiently couple with o- dibromobenzenes in the presence of a palladium catalyst and a base to give the corresponding oxygen-containing heterocycles or carbocyclic compounds. Thus, from the reactions of benzyl phenyl ketones, 1-naphthols, and α,β- unsaturated aldehydes and ketones, benzofuran, benzopyran, benzocyclobutane, and indene derivatives, respectively, are produced selectively via the successive formation of C-C and C-O bonds or of two C-C bonds.

Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent

Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.

Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis

Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1)participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5)and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29)as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.

Iridium-Catalyzed Aerobic Coupling of Salicylaldehydes with Alkynes: A Remarkable Switch of Oxacyclic Product

The iridium(III)/copper(II)-catalyzed dehydrogenative coupling of salicylaldehydes with internal alkynes proceeds efficiently under atmospheric oxygen through aldehyde C?H bond cleavage and decarbonylation. A variety of benzofuran derivatives can be synthesized by the environmentally benign procedure. DFT calculations suggest that this unique transformation involves the facile deinsertion of CO in the key metallacycle intermediate, which is in marked contrast to the corresponding rhodium(III) catalysis that leads to CO-retentive chromone derivatives.

Acid-promoted furan annulation and aromatization: An access to benzo[b]furan derivatives

An unprecedented PTSA-promoted furan annulation and aromatization in one pot has been developed. This process offers a simple and efficient synthetic route for the construction of various highly substituted benzo[b]furan derivatives, which are widely used not only in drug active molecules but also organic semiconductor and organic light-emitting devices. The preliminary mechanism study indicated this transformation proceeded sequentially via furan annulation and aromatization.

Photoinduced Gold-Catalyzed Domino C(sp) Arylation/Oxyarylation of TMS-Terminated Alkynols with Arenediazonium Salts

A selective and convenient synthesis of tri- and tetrasubstituted α,β-unsaturated ketones, as well as 2,3-diarylbenzofurans has been developed with the aid of light and taking advantage of a cooperative gold/photoredox-catalyzed 2-fold arylation reaction of TMS-terminated alkynols. The reaction of 3-(trimethylsilyl)prop-2-yn-1-ols was competent to generate diarylated α,β-unsaturated ketones; whereas the photoredox sequence involving 2-[(trimethylsilyl)ethynyl]phenol exclusively afforded 2,3-diarylbenzofurans. The reaction of terminal alkynes proceeded in poor yields while the use of bulkier silyl groups, such as TIPS, resulted unproductive. Apparently, the C(sp) arylation reaction is the first event on the domino bis-arylative sequence. These results could be explained through the intermediation of arylgold(III) species and several single electron transfer processes.

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

A regio- and chemoselective cross-coupling study using 2,3-dibromobenzofurans and 2,3,5-tribromobenzofuran was achieved with sub-stoichiometric loadings of triarylbismuths as atom-economic reagents under Pd-catalyzed conditions. As part of this study, various 2,3-diaryl- and 2,3,5-triarylbenzofuran products were obtained in high yields, involving one-pot operations and short reaction times.