26870-36-0

Basic information

• Product Name: 4-(benzofuran-2-yl)phenol
• Synonyms: 4-(benzofuran-2-yl)phenol;4-(2-Benzofuranyl)-phenol
• CAS NO: 26870-36-0
• Molecular Formula: C₁₄H₁₀O₂
• Molecular Weight: 210.228
• Mol File: 26870-36-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(benzofuran-2-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(benzofuran-2-yl)phenol(26870-36-0)
• EPA Substance Registry System: 4-(benzofuran-2-yl)phenol(26870-36-0)

Safety Data

• Hazardous Substances Data: 26870-36-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(benzofuran-2-yl)phenol serves as a crucial building block in the synthesis of a variety of drugs. Its inherent biological activities, such as antioxidant and anti-inflammatory properties, contribute to the development of medications aimed at treating different medical conditions.
Used in Anticancer Applications:
4-(benzofuran-2-yl)phenol is being studied for its potential anticancer effects, suggesting that it could be utilized as an anticancer agent. Its ability to target and mitigate cancerous cells could make it a valuable component in cancer treatment regimens.
Used in Neuroprotective Applications:
4-(benzofuran-2-yl)phenol has also been investigated for its neuroprotective properties, indicating its potential use in the development of treatments for neurological disorders and conditions where neuronal protection and preservation are critical.
Used in Antioxidant and Anti-inflammatory Therapies:
Given its antioxidant and anti-inflammatory characteristics, 4-(benzofuran-2-yl)phenol can be employed in therapies that require mitigation of oxidative stress and inflammation, which are common in a variety of diseases and conditions.

Upstream product

• 19234-04-9 2-(p-methoxyphenyl)-benzo[b]furan 
• 65200-70-6 2-(2-methoxyphenyl)-1-(4-methoxyphenyl)ethan-1-one 
• 701262-43-3 (E)-1-(4-hydroxyphenyl)ethanone O-phenyloxime 
• 4846-21-3 O-phenylhydroxylamine 
• 99-93-4 4-Hydroxyacetophenone 
• 858237-53-3 4,2'-dimethoxystilbene 
• 70340-04-4 (2-hydroxybenzyl)triphenylphosphonium bromide 
• 156-38-7 4-hydroxyphenylacetate 
• 6468-98-0 3-(4-hydroxyphenyl)-2H-chromen-2-one 
• 90-02-8 salicylaldehyde 
• 90-01-7 salicylic alcohol 
• 1542580-99-3 C₁₇H₁₆O₄ 
• 1548157-96-5 C₁₇H₁₆O₄ 
• 98437-24-2 benzofuran-2-boronic acid 

Downstream Products

• 258875-77-3 2-(4-(3-bromopropoxy)phenyl)benzofuran 
• 57664-51-4 2-[4'-(3-diethylaminopropoxy)phenyl]benzofuran 
• 1025740-45-7 2-[4-(7-bromoheptyloxy)phenyl]benzofuran 
• 1375085-41-8 C₁₇H₁₇NO₂ 
• 1375085-42-9 C₁₈H₁₉NO₂ 
• 57664-56-9 2-(4-(2-bromoethoxy)phenyl)benzofuran 
• 1416452-75-9 2-[4-(5-chloropentyloxy)phenyl]benzofuran 
• 1416452-21-5 C₂₇H₂₉NO₂ 
• 1416452-78-2 2-[4-(8-bromooctyloxy)phenyl]benzofuran 
• 1416452-25-9 C₃₀H₃₅NO₂ 
• 1416452-80-6 2-[4-(9-bromononyloxy)phenyl]benzofuran 
• 1416452-30-6 C₃₁H₃₇NO₂ 
• 1416452-41-9 C₄₄H₄₁NO₃ 
• 1416452-99-7 [2-(4-{7-[(3-hydroxybenzyl)-N-methylamino]heptyloxy}phenyl)benzofuran-3-yl]-p-tolylmethanone 

Relevant articles and documents

An expeditious synthesis of polyhydroxylated 2-arylbenzo[b]furans

An expeditious synthesis of polyhydroxylated 2-arylbenzo[b]furans is described. The key steps are the conversion of the corresponding polymethoxylated stilbenes into diarylethanoid molecules (epoxide or alcohol) that were demethylated and cyclised using boron tribromide to give the target polyhydroxylated 2-arylbenzo[b]furans.

Acid-mediated intermolecular C-F/C-H cross-coupling of 2-fluorobenzofurans with arenes: Synthesis of 2-arylbenzofurans

Transition-metal-free acid-promoted biaryl construction was achieved via intermolecular C-F/C-H cross-coupling. By treating 2-fluorobenzofurans with arenes in the presence of AlCl3, 2-arylbenzofurans were obtained. This protocol was successfully applied to the short-step orthogonal synthesis of a bioactive 2-arylbenzofuran natural product, which allows independent transformations of C-F and C-Br bonds. Mechanistic studies indicated that α-fluorine-stabilized carbocations, generated via the protonation of 2-fluorobenzofurans, served as key intermediates. The Friedel-Crafts-type C-C bond formation between the α-fluorocarbocations and arenes, followed by hydrogen fluoride elimination, afforded 2-arylbenzofurans. This journal is

2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling

A series of 2-phenylbenzofurans compounds was designed, synthesized and evaluated as cholinesterase inhibitors. The biological assay experiments showed that most of the compounds displayed a clearly selective inhibition for butyrylcholinesterase (BChE), while a weak or no effect towards acetylcholinesterase (AChE) was detected. Among these benzofuran derivatives, compound 16 exhibited the highest BChE inhibition with an IC50 value of 30.3 μM. This compound was found to be a mixed-type inhibitor as determined by kinetic analysis. Moreover, molecular dynamics simulations revealed that compound 16 binds to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of BChE and it displayed the best interaction energy value, in agreement with our experimental data.

ALIGNMENT COMPOUNDS

The present invention relates to compounds represented by the following Formula (I). With reference to Formula (I), at least one of E1 and E2 independently is, or is independently substituted with, at least one reactive group, such as a (meth)acryloyl group. The compounds of the present invention can be used alone and/or in combination with polymers prepared from such compounds, such as to form or as one or more components of an alignment layer.

An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides

An efficient and practical method for construction of 2-arylbenzo[b]furans from 2-methoxychalcone epoxides has been reported. Catalyzed by 2 mol % of BF3·Et2O, 2-methoxychalcone epoxides went through the Meerwein rearrangement, followed by deformylation in one-pot to successfully afforded 2-methoxydeoxybenzoins. Afterward, 2-arylbenzo[b]furans were obtained in high yields (87%-100%) via intermolecular cyclodehydration of 2-methoxydeoxybenzoins with 48% HBr. By utilization of this approach, the natural product stemofuran A and the key intermediate of eupomatenoid 6 have been synthesized conveniently.

Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids

A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC50 value of 0.017 μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD.

Synthesis of 2-phenylbenzofuran derivatives and selective binding activities on estrogen receptor

An improved chemical reaction protocol with short time and easy work-up was described here for 2-phenylbenzofuran derivatives. The final purified products, 2-phenylbenzofuran derivatives 5a-g and the intermediate diols 4a-g, were evaluated for their estrogen receptor (ER) binding affinity and selective activity in vitro. Among these fourteen tested compounds, 4g and 5g showed higher binding affinity on ER subtypes, ERα and ERβ. Compound 4g exhibited preferable ERα binding, while 5g was more estrogen selective for ERβ. The molecular docking was also performed to explore the detailed interactive interface between ER and the compounds.

Synthesis of fluorinated 2,3-disubstituted benzofurans potential β-amyloid aggregation inhibitors

A convenient synthesis of 2-[4'-(3-diethylaminopropoxy)phenyl]-3(2-fluorobenzoyl)benzofuran, 3-(4-fluorobenzoyl)- and 3-(4-trifluoromethylbenzoyl) derivatives, via the Suzuki cross-coupling reaction as the key transformation, is described.

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans

A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: Short syntheses of stemofuran A and eupomatenoid 6

Matrix presented. A new and efficient synthesis of 2-arylbenzofurans has been achieved via a route involving acylation and subsequent [3,3]-sigmatropic rearrangement of oxime ethers. Its synthetic utility is demonstrated by a short synthesis of stemofuran