3261-05-0

Basic information

• Product Name: 5-CHLORO-BENZOFURAN-3-ONE
• Synonyms: 5-CHLORO-BENZOFURAN-3-ONE;5-Chloro-3(2H)-benzofuranone;5-Bromo-3-Benzofuranone;5-Chloro-1-benzofuran-3(2H)-one;5-chlorobenzofuran-3(2H)-one;5-Chlorocoumaran-3-one, 5-Chloro-2,3-dihydro-3-oxo-1-benzofuran, 5-Chloro-2,3-dihydro-3-oxobenzo[b]furan
• CAS NO: 3261-05-0
• Molecular Formula: C₈H₅ClO₂
• Molecular Weight: 168.58
• Product Categories: pharmacetical
• Mol File: 3261-05-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 117 °C
• Boiling Point: 304.3 °C at 760 mmHg
• Flash Point: 145.6 °C
• Appearance: /
• Density: 1.428 g/cm³
• Vapor Pressure: 0.00088mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLORO-BENZOFURAN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-BENZOFURAN-3-ONE(3261-05-0)
• EPA Substance Registry System: 5-CHLORO-BENZOFURAN-3-ONE(3261-05-0)

Safety Data

• Hazardous Substances Data: 3261-05-0(Hazardous Substances Data)

Usage

Uses

5-Chloro-benzofuran-3-one is a useful reactant for the synthesis of 2-?(2-?hydroxypropan-?2-?yl)?benzofuran-?3(2H)?-?ones in a more environment-?friendly process.

InChI:InChI=1/C8H5ClO2/c9-5-1-2-8-6(3-5)7(10)4-11-8/h1-3H,4H2

Upstream product

• 186581-53-3 diazomethane 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 623-12-1 4-chloromethoxybenzene 
• 79-04-9 chloroacetyl chloride 
• 3261-07-2 chloro-acetic acid-(4-chloro-phenyl ester) 
• 71643-66-8 4-chloro-2-iodo phenol 
• 4122-68-3 4-chlorophenyloxyacetyl chloride 
• 95186-47-3 4-chloro-2-ethynyl-1-methoxybenzene 
• 670-62-2 methyl 5-chloro-2-(2-ethoxy-2-oxoethoxy)benzoate 
• 62755-94-6 ethyl 5-chloro-3-hydroxy-1-benzofuran-2-carboxylate 
• 960063-92-7 3-acetoxy-5-chloro-benzofuran 
• 24483-75-8 2-chloro-1-(5-chloro-2-hydroxy-phenyl)-ethanone 
• 334758-22-4 2-carboxymethoxy-5-chloro-benzoic acid 

Downstream Products

• 62877-31-0 5-chloro-2-morpholin-4-ylmethyl-benzofuran-3-ol 
• 97211-83-1 8-chloro-10H-benzofuro[3,2-b]indole 
• 139221-04-8 2-(2-cyano-2-ethoxycarbonylvinyl)-3-hydroxy-5-chlorobenzofuran 
• 139313-77-2 (5-Chloro-benzofuran-3-yl)-acetonitrile 
• 669-66-9 5-chloro-benzofuran-3-one oxime 
• 960064-19-1 C₁₃H₈ClN₃O₄ 
• 960064-03-3 C₁₃H₈ClN₃O₄ 
• 1243205-05-1 3-azido-5-chloro-2,3-dihydro-1-benzofuran 
• 669-45-4 5-chloro-2,3-dihydro-1-benzofuran-3-amine hydrochloride 
• 1387634-98-1 5-chloro-2-(5-chlorobenzofuran-3-yl)-3-methoxybenzofuran 
• 1387635-00-8 5-chloro-2-(5-chlorobenzofuran-3-yl)-3-ethoxybenzofuran 
• 23145-05-3 5-chlorobenzofuran 
• 223576-64-5 (5-chlorobenzofuran-2-yl)boronic acid 

Relevant articles and documents

Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2

In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series of aurones have been synthesized. These compounds are structurally related to the synthetic flavones and showed nanomolar activities towards CK2. Biochemical tests revealed that 20 newly synthesized compounds inhibited CK2 with IC50 values in the nanomolar range. Further property-based optimization of aurones was performed, yielding a series of CK2 inhibitors with enhanced lipophilic efficiency. The most potent compound 12m (BFO13) has CLipE = 4.94 (CLogP = 3.5; IC50 = 3.6 nM) commensurable with the best known inhibitors of CK2.

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.

Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy

A gold-catalyzed intermolecular alkyne oxidation for the preparation of 3-coumaranones has been developed. Using 8-isopropylquinoline N-oxides as oxidants, the reactions of o-ethynylanisoles afford versatile 3-coumaranones in moderate to good isolated yields. The synthetic utility of this chemistry is also indicated by the synthesis of the natural product sulfuretin.