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

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

• 24483-75-8 2-chloro-1-(5-chloro-2-hydroxy-phenyl)-ethanone 
• 186581-53-3 diazomethane 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 106-48-9 4-chloro-phenol 
• 122-88-3 4-Chlorophenoxyacetic acid 
• 623-12-1 4-chloromethoxybenzene 
• 79-04-9 chloroacetyl chloride 
• 71643-66-8 4-chloro-2-iodo phenol 
• 3261-07-2 chloro-acetic acid-(4-chloro-phenyl ester) 
• 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 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 

Downstream Products

• 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 
• 139313-78-3 2-(5-Chloro-benzofuran-3-yl)-N-hydroxy-acetamidine 
• 128105-08-8 4-[(5-chloro-3-benzofuranyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide 
• 82156-63-6 ethyl (5-chloro-1-benzofuran-3-yl)acetate 
• 5590-44-3 5-chloro-2,3-dihydro-benzofuran-3-ol 
• 74814-87-2 (Z)-4'-(5-Tetrazolyl)-2-benzylidene-5-chlorobenzofuran-3(2H)-one 
• 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 

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.

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.

Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus

In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential.

NOVEL HETEROARYL IMIDAZOLES AND HETEROARYL TRIAZOLES AS GAMMA-SECRETASE MODULATORS

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I; (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

NOVEL PHENYL IMIDAZOLES AND PHENYL TRIAZOLES AS GAMMA-SECRETASE MODULATORS

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed

Novel benzofuran derivatives with dual 5-HT1A receptor and serotonin transporter affinity

Several benzofuran derivatives linked to a 3-indoletetrahydropyridine through an alkyl chain were prepared and evaluated for serotonin transporter and 5-HT1A receptor affinities. Their design, synthesis and structure-activity relationships are described.

BENZOFURANYL- AND BENZOTHIENYL- PIPERAZINYL QUINOLINES AND METHODS OF THEIR USE

Benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.

Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2 H)-benzofuranone derivatives

A new series of (Z)-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2 H)-benzofuranones (11a-p) and (Z)-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2 H)-benzofuranones (12a-m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a-p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a-m) were not effective against selected bacteria. The quantitative structure-activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities.