57329-30-3

Basic information

• Product Name: Benzofuran, 3-(4-chlorophenyl)-
• CAS NO: 57329-30-3
• Molecular Formula: C14H9ClO
• Molecular Weight: 228.678
• Mol File: 57329-30-3.mol

Chemical Properties

• CAS DataBase Reference: Benzofuran, 3-(4-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzofuran, 3-(4-chlorophenyl)-(57329-30-3)
• EPA Substance Registry System: Benzofuran, 3-(4-chlorophenyl)-(57329-30-3)

Safety Data

• Hazardous Substances Data: 57329-30-3(Hazardous Substances Data)

Upstream product

• 533-58-4 2-Iodophenol 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 1579264-19-9 2-(1-(4-chlorophenyl)vinyl)phenol 
• 95-56-7 2-hydroxybromobenzene 
• 75230-50-1 p-chloroacetophenone tosylhydrazone 
• 59214-70-9 3-bromobenzofuran 
• 1679-18-1 4-Chlorophenylboronic acid 
• 108-95-2 phenol 
• 271-89-6 1-benzofurane 
• 106-39-8 bromochlorobenzene 
• 127-19-5 N,N-dimethyl acetamide 
• 2985-79-7 4'-chloro-2-hydroxybenzophenone 
• 637-87-6 1-Chloro-4-iodobenzene 
• 90-02-8 salicylaldehyde 

Relevant articles and documents

Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl Halides to Aryl Ketones for the Synthesis of Benzofuran Derivatives

A nickel-catalyzed intramolecular nucleophilic addition reaction of aryl halides to aryl ketones for the formation of benzofuran derivatives has been developed. A number of substrates bearing electron-donating or electron-withdrawing groups were subjected to the standard reaction conditions, giving the corresponding products in moderate to good yields.

Sequential One-Pot Synthesis of 3-Arylbenzofurans from N-Tosylhydrazones and Bromophenol Derivatives

A divergent and efficient one-pot sequence allowing direct access to 3-arylbenzofuran derivatives has been developed. The process, involving N-tosylhydrazones and bromophenols, proceeds via a palladium-catalyzed Barluenga-Valdés cross-coupling, followed by an aerobic, copper-catalyzed, radical cyclization to form Csp2-Csp2 and O-Csp2 bonds. 3-Arylated benzofurans bearing various substituents were obtained with good to excellent yields (up to 90%). Mechanistic investigation strongly supports a radical process for the cyclization step.

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.

Exogenous-oxidant-free electrochemical oxidative C-H sulfonylation of arenes/heteroarenes with hydrogen evolution

An efficient and environmentally benign electrochemical oxidative radical C-H sulfonylation of arenes/heteroarenes was developed in this work. A series of significant diarylsulfones were prepared under mild catalyst- and exogenous-oxidant-free reaction conditions, which efficiently avoid the issues of desulfonylation or over-reduction of sulfonyl groups.

Synthesis of 3-aryl-benzo[b]furans and 3-aryl-naphtho[b]furans using n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride immobilised on SiO2 as an efficient and reusable catalyst

A new and convenient method is described for the synthesis of 3-aryl-benzo[b]furans and 3-aryl-naphtho[b]furans by the reaction of various α-bromoketones with phenols and 2-naphthols in the presence of n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride

Direct arylation of benzo[b]furan and other benzo-fused heterocycles

The direct arylation of benzo[b]furan, benzo[b]thiophene, and indole has been studied by using aromatic bromides as the aryl source. The protocol employing common reagents and a Pd catalyst has led to the regioselective arylation of these heterocycles at the 2-position. A range of functional groups were tolerated, providing quick access to a variety of arylated benzo-fused heterocycles that would be accessible more elaborately using classical synthetic strategies. This is the first systematic study of the direct arylation of benzo[b]-furan.

Benzofurans from benzophenones and dimethylacetamide: Copper-promoted cascade formation of furan O1-C2 and C2-C3 bonds under oxidative conditions

DMA donates: Copper(II) acetate and 8-hydroxyquinoline promote the formation of a benzofuran core through a cascade of copper-catalyzed processes wherein the key carbon atom comes from the dimethylacetamide (DMA) solvent. Strong evidence for the participation of a Wacker cyclization catalyzed solely by copper is provided, not only in the title reaction from benzophenones but also from 2-hydroxy-α-arylstyrene derivatives. Copyright

Palladium(II)-catalyzed intramolecular addition of arylboronic acids to ketones

A palladium(II)-catalyzed intramolecular addition of arylboronic acids to ketones was developed. Compared to Pd(OAc)2 catalysis system, cationic palladium complex with dppp as the ligand has higher catalytic activity and efficiency for wider sc

Palladium assisted substitution of 3-benzo[b]furan triflates

Triflates of 3-coumaranones were prepared, and experimented as coupling partners in palladium catalyzed Stille, Heck, Suzuki, and Sonogashira coupling reactions. The corresponding 3-substituted benzo[b]furans were obtained in excellent yields.