6272-26-0

Basic information

• Product Name: 6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one
• Synonyms: AKOS BBS-00001298;6-HYDROXYBENZOFURAN-3(2H)-ONE;6-HYDROXY-3-COUMARANONE;6-HYDROXY-2,3-DIHYDROBENZO[B]FURAN-3-ONE;6-HYDROXY-2H-BENZOFURAN-3-ONE;6-Hydroxy-3-coumaranone~6-Hydroxy-2,3-dihydro-1-benzofuran-3-one;6-hydroxy-2,3-dihydro-1-benzofuran-3-one;6-HYDROXY-1-BENZOFURAN-3(2H)-ONE
• CAS NO: 6272-26-0
• Molecular Formula: C₈H₆O₃
• Molecular Weight: 150.13
• Product Categories: Heterocyclic Compounds;Heterocycle;Fused Ring Systems;Heterocyclic Building Blocks;O-Containing;Others;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 6272-26-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 242-246 °C (dec.)(lit.)
• Boiling Point: 369.3 °C at 760 mmHg
• Flash Point: 162.6 °C
• Appearance: yellow crystalline powder or chunks
• Density: 1.436 g/cm³
• Vapor Pressure: 5.66E-06mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.63±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 121444
• CAS DataBase Reference: 6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one(6272-26-0)
• EPA Substance Registry System: 6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one(6272-26-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 6272-26-0(Hazardous Substances Data)

Usage

Description

6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one is an organic compound characterized by its faint yellow to brown powder appearance. It is a derivative of benzo[b]furan, a type of heterocyclic compound, and features a hydroxyl group at the 6th position and a carbonyl group at the 3rd position. 6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one is known for its potential applications in various industries, particularly as a pharmaceutical intermediate.

Uses

Used in Pharmaceutical Industry:
6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one is used as a pharmaceutical intermediate for the synthesis of various drugs and medicinal compounds. Its unique chemical structure allows it to serve as a building block in the development of new pharmaceuticals, potentially contributing to the creation of novel treatments for a range of health conditions.
As a chemical intermediate, 6-Hydroxy-2,3-dihydrobenzo[b]furan-3-one can be further modified or reacted with other compounds to produce a variety of pharmaceutically active substances. Its versatility in chemical reactions makes it a valuable asset in the field of drug discovery and development.

InChI:InChI=1/C8H6O3/c9-5-1-2-6-7(10)4-11-8(6)3-5/h1-3,9H,4H2

Upstream product

• 59354-24-4 chloroacetonitrile 
• 108-46-3 recorcinol 
• 79-04-9 chloroacetyl chloride 
• 107-14-2 chloroacetonitrile 
• 91634-23-0 4-acetoxy-2-methoxybenzoic acid 
• 1878-83-7 3-hydroxyphenoxyacetic acid 
• 755722-84-0 imine 
• 2491-39-6 2-bromo-2',4'-dihydroxyoacetophenone 
• 84356-87-6 C₂₃H₁₅ClO₈ 
• 84356-90-1 5-[Bis-(6-hydroxy-3-oxo-2,3-dihydro-benzofuran-2-yl)-methyl]-3-chloro-[1,2]benzoquinone 
• 57280-75-8 2',4'-dihydroxy-2-methoxyacetophenone 
• 10035-10-6 hydrogen bromide 
• 76681-74-8 C₂₃H₁₆O₈ 
• 90921-05-4 3-oxo-2,3-dihydrobenzofuran-6-yl acetate 

Downstream Products

• 848567-12-4 (Z)-6-hydroxy-2-(4-(trifluoromethyl)benzylidene)benzofuran-3(2H)-one 
• 139149-22-7 (E/Z)-6-benzyloxy-2,3-dihydrobenzofuran-3-oxime 
• 139149-23-8 N-[6-Benzyloxy-2,3-dihydrobenzofuran-3-yl]-hydroxylamine 
• 161953-16-8 6-(2.6-Diflurobenzyloxy)-3-oximino-2,3-dihydrobenzofuran 
• 726174-52-3 (6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester 
• 210360-63-7 (Z)-2-(2,4-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one 
• 15832-09-4 6-methoxy-3-coumaranone 
• 61429-80-9 (2Z)-6-hydroxy-2-[(3-hydroxyphenyl)methylene]benzofuran-3-one 
• 1234351-94-0 (Z)-6-hydroxy-2-(4-methylbenzylidene)benzofuran-3(2H)-one 
• 1234351-74-6 (2Z)-2-(2-chlorobenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one 
• 5786-54-9 (Z)-6-hydroxy-2-(4-hydroxybenzylidene)benzofuran-3(2H)-one 
• 1234351-77-9 (Z)-6-hydroxy-2-(3-chlorobenzylidene)benzofuran-3(2H)-one 
• 1234351-86-0 (Z)-6-hydroxy-2-(2-methoxybenzylidene)benzofuran-3(2H)-one 
• 1234351-92-8 (Z)-4-((6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl)benzonitrile 

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.

PD-1/PD-L1 small-molecule inhibitor and preparation method and application thereof

The invention discloses a PD-1/PD-L1 small-molecule inhibitor and a preparation method and application thereof. Specifically, the invention discloses a compound with the structure shown in the formulaL, a stereoisomer or a tautomer thereof, or pharmaceutically acceptable salts or hydrates or solvates thereof, and please see the specification for specific definitions. The compound has excellent effects for restraining PD-1/PD-L1. Please see the specification for the formula.

Aurones as new porcine pancreatic α-amylase inhibitors

Background: Aurones, (Z)-2-benzylidenebenzofuran-3-one derivatives, are naturally-occurring structural isomers of flavones, with promising pharmacological potential. Methods: In this study, the structural requirements for the inhibition of porcine pancreatic α-amylase by hydroxylated or methoxylated aurone derivatives were investigated by assessing their in vitro biological activities against porcine pancreatic α-amylase. Results: The structure-activity relationship of these inhibitors based on both in vitro and in silico findings showed that the hydrogen bonds between the OH groups of the A or B ring of (Z)-benzylidenebenzofuran-3-one derivatives and the catalytic residues of the binding site are crucial for their inhibitory activities. Conclusion: It seems that the OH groups in aurones inhibit α-amylase in a manner similar to that of OH groups in flavones and flavonols.