7196-05-6

Basic information

• Product Name: 5-METHOXY-3-PHENYLBENZOFURAN
• Synonyms: 5-METHOXY-3-PHENYLBENZOFURAN
• CAS NO: 7196-05-6
• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.25
• Mol File: 7196-05-6.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-METHOXY-3-PHENYLBENZOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-3-PHENYLBENZOFURAN(7196-05-6)
• EPA Substance Registry System: 5-METHOXY-3-PHENYLBENZOFURAN(7196-05-6)

Safety Data

• Hazardous Substances Data: 7196-05-6(Hazardous Substances Data)

Upstream product

• 53074-73-0 2-(2-chloroacetyl)phenol 
• 100-58-3 phenylmagnesium bromide 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 150-76-5 4-methoxy-phenol 
• 70-11-1 α-bromoacetophenone 
• 62594-98-3 4-methoxy-2-(1-phenylethenyl)phenol 
• 536-74-3 phenylacetylene 
• 14385-49-0 8-(4'-methoxyphenoxy)acetophenone 

Downstream Products

• 7291-76-1 5-hydroxy-3-phenylbenzofuran 

Relevant articles and documents

B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with Phenols

We developed a B(C6F5)3 catalyzed hydroarylation of terminal alkynes with various phenols at room temperature without adding any additives, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. Those transformations featured a broad substrate scope with moderate yields. Mechanism studies indicated that those transformations proceeded through the activation of phenol by B(C6F5)3 with subsequent protonation of alkyne/Friedel-Crafts-type reaction. (Figure presented.).

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.