25158-68-3

Basic information

• Product Name: 5-nitro-1-benzofuran-3(2H)-one
• Synonyms: 3(2H)-benzofuranone, 5-iodo-; 5-Iodo-1-benzofuran-3(2H)-one
• CAS NO: 25158-68-3
• Molecular Formula: C₈H₅NO₄
• Molecular Weight: 260.0286
• Mol File: 25158-68-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 341.3°C at 760 mmHg
• Flash Point: 160.2°C
• Density: 2.029g/cm³
• Vapor Pressure: 8.1E-05mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: 5-nitro-1-benzofuran-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-nitro-1-benzofuran-3(2H)-one(25158-68-3)
• EPA Substance Registry System: 5-nitro-1-benzofuran-3(2H)-one(25158-68-3)

Safety Data

• Hazardous Substances Data: 25158-68-3(Hazardous Substances Data)

Upstream product

• 5037-70-7 2-bromo-1-(2-hydroxy-5-nitrophenyl)ethanone 
• 100-17-4 para-methoxynitrobenzene 
• 79-04-9 chloroacetyl chloride 
• 97-51-8 5-Nitrosalicylaldehyde 
• 885951-98-4 2-ethynyl-4-nitrophenol 
• 77123-62-7 1-ethynyl-2-methoxy-5-nitrobenzene 
• 53074-73-0 2-(2-chloroacetyl)phenol 

Downstream Products

• 1093451-04-7 C₁₆H₁₁NO₅ 

Relevant articles and documents

A Hg(OTf)2-Catalyzed Enolate Umpolung Reaction Enables the Synthesis of Coumaran-3-ones and Indolin-3-ones

The potential of mercury catalysis has been extended to the arena of enolate umpolung reactions for the first time by the generation of enolonium species via Hg(OTf)2-catalyzed N-oxide addition to alkynes. The enolonium species formed can undergo intramolecular nucleophilic attack by hydroxyl or amino groups, leading to the synthesis of various coumaran-3-ones and indolin-3-ones.

Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis

Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50value of 3.15?μM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50?=?0.33?μM) and 41 (IC50?=?0.25?μM) were found to protect islet β-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.

4-Substituted-7-azaindoles bearing a ureidobenzofuranone moiety as potent and selective, ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)

A series of 5-ureidobenzofuranones was discovered as potent and selective inhibitors of mTOR with good cellular activity. Molecular modeling studies revealed several hydrogen bond interactions of the ureido group with the enzyme at the ATP-binding site. Furthermore, modeling showed that the ureido group is best situated at C-5 of the benzofuranone. Syntheses of 4-ureido and 5-ureidobenzofuranones are presented.