83790-87-8

Basic information

• Product Name: (2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone
• Synonyms: (2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone;Einecs 280-851-4;(2-butylbenzofuran-3-yl)(4-Methoxyphenyl)Methanone;AMiodarone Methoxy IMpurity;De(diethylaMinoMethyldiiodo) AMiodarone
• CAS NO: 83790-87-8
• Molecular Formula: C₂₀H₂₀O₃
• Molecular Weight: 308.371
• EINECS: 280-851-4
• Mol File: 83790-87-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 472°C at 760 mmHg
• Flash Point: 239.3°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 4.43E-09mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: (2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone(CAS DataBase Reference)
• NIST Chemistry Reference: (2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone(83790-87-8)
• EPA Substance Registry System: (2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone(83790-87-8)

Safety Data

• Hazardous Substances Data: 83790-87-8(Hazardous Substances Data)

Usage

General Description

(2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone, also known as 2-(2-butylbenzofuran-3-yl)-1-(4-methoxyphenyl)ethanone, is a chemical compound with a complex and specific structure. It is often used in the synthesis of pharmaceuticals and other organic compounds due to its unique molecular configuration. The compound contains a ketone group and a benzofuran ring, which makes it useful for applications in medicinal chemistry and drug discovery. Additionally, the presence of a methoxyphenyl group adds further versatility to its chemical properties. Overall, this compound has the potential for various applications in the field of organic chemistry and drug development.

InChI:InChI=1/C20H20O3/c1-3-4-8-18-19(16-7-5-6-9-17(16)23-18)20(21)14-10-12-15(22-2)13-11-14/h5-7,9-13H,3-4,8H2,1-2H3

Upstream product

• 75-44-5 phosgene 
• 4265-27-4 2-n-butylbenzo[b]furan 
• 75-34-3 1,1-dichloroethane 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-73-2 acrolein dimer 
• 1137261-90-5 1-(4-methoxyphenyl)-1,3-heptanedione 
• 693-02-7 hex-1-yne 
• 533-58-4 2-Iodophenol 
• 624-24-8 methyl valerate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 100-09-4 4-methoxybenzoic acid 
• 138320-27-1 2-(2-formyl-phenoxy)-hexanoic acid 
• 138320-26-0 methyl 2-(2-formylphenoxy)hexanoate 
• 5445-19-2 methyl 2-bromohexanoate 

Downstream Products

• 52490-15-0 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran 
• 1951-26-4 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran 
• 1951-25-3 Amiodarone 
• 19774-82-4 amiodarone hydrochloride 

Relevant articles and documents

Benzofuran compound and application thereof

The invention provides a benzofuran compound as shown in a formula (I) or pharmaceutically acceptable salt thereof, and application thereof. The compound can selectively inhibit activation of NLRP3 inflammasomes and inhibit maturation and secretion of inflammation activation signal molecules Caspase-1 and P20 and inflammatory cytokines IL-1beta, has a good prevention and treatment effect on NLRP3 inflammasome related diseases, and particularly has a remarkable prevention and treatment effect on peritonitis and gouty arthritis. Therefore, the compound can be used for preparing drugs for treating NLRP3 inflammasome-related diseases, such as anti-inflammatory drugs or auxiliary anti-inflammatory drugs.

Discovery of dronedarone and its analogues as NLRP3 inflammasome inhibitors with potent anti-inflammation activity

Inhibiting NLRP3 inflammasome activation is a prospective therapeutic strategy for uncontrolled inflammatory diseases. It is the first time that dronedarone, a multiply ion channel blocker, was identified as a NLRP3-inflammasome inhibitor with an IC50 value of 6.84 μM against IL-1β release. A series of novel 5-amide benzofuran derivatives were designed and synthesized as NLRP3-inflammasome inhibitors. Compound 8c showed slightly increased activity (IC50 = 3.85 μM) against IL-1β release. Notably, treatment with 8c could significantly inhibit NLRP3-mediated IL-1β release and ameliorate peritoneal inflammation in a mouse model of sepsis. Collectively, 8c is a promising lead compound for further chemical development as a NLRP3 inhibitor with anti-inflammation effects.

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.