141627-42-1

Basic information

• Product Name: (2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone
• Synonyms: (2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone;2-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran;Methanone, (2-butyl-5-nitro-3-benzofuranyl)(4-methoxyphenyl)-;2-butyl-3-[(4-Methoxyphenyl)carbonyl]-5-nitro-1-benzofuran;(2-butyl-5-nitro-3-benzofuranyl)(4-methoxyphenyl)Methanone;Dronedarone Impurity E;(2-butyl-5-nitro-1-benzofuran-3-yl)-(4-methoxyphenyl)methanone
• CAS NO: 141627-42-1
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.372
• EINECS: 1806241-263-5
• Product Categories: API
• Mol File: 141627-42-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 537.726 °C at 760 mmHg
• Flash Point: 279.007 °C
• Appearance: Off-white crystalline
• Density: 1.235 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: (2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone(141627-42-1)
• EPA Substance Registry System: (2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone(141627-42-1)

Safety Data

• Hazardous Substances Data: 141627-42-1(Hazardous Substances Data)

Usage

Uses

(2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone is a reagent in the preparation of heterocyclic benzofuran carboxamides via amidation of heterocyclic acyl chlorides with benzofuranamine. This is also a derivative of Dronedarone (D679445),which is a drug used for the treatment of atrial fibrillation and atrial flutter in patients who have suffered cardiac arrhythmias.

InChI:InChI=1/C20H19NO5/c1-3-4-5-18-19(20(22)13-6-9-15(25-2)10-7-13)16-12-14(21(23)24)8-11-17(16)26-18/h6-12H,3-5H2,1-2H3

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 133238-87-6 2-(n-butyl)-5-nitrobenzofuran 
• 1256921-45-5 2-(2-pentanoyloxy-5-nitrophenyl)-1-(4-methoxyphenyl)-ethanone 
• 1257220-33-9 2-(2-hydroxy-5-nitrophenyl)-1-(4-methoxyphenyl)-1,3-heptandione 
• 638-29-9 n-valeryl chloride 
• 772-33-8 Koshlands reagent I 
• 6411-34-3 4-allyloxyphenol 
• 1137261-90-5 1-(4-methoxyphenyl)-1,3-heptanedione 
• 70726-17-9 (2-hydroxy-5-nitrobenzyl)triphenylphosphine chloride 
• 2973-19-5 2-hydroxy-5-nitrobenzyl chloride 
• 142-61-0 Hexanoyl chloride 
• 1393093-68-9 2-bromo-1-(2-hydroxy-5-nitrophenyl)hexan-1-one 
• 1393093-67-8 2-bromo-1-(2-methoxy-5-nitrophenyl)hexan-1-one 
• 1393093-66-7 1-(2-methoxy-5-nitrophenyl)hexan-1-one 

Downstream Products

• 1278585-69-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)acetamide 
• 141626-57-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)-benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide 
• 141626-36-0 dronedarone 
• 1309476-89-8 (4-(3-chloropropoxy)phenyl)(5-amino-2-butylbenzofuran-3-yl)methanone 
• 1310430-03-5 (4-(3-chloropropoxy)phenyl)(2-butyl-5-nitrobenzofuran-3-yl)methanone 

Relevant articles and documents

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.

Electrochemical Cross-Dehydrogenative Coupling between Phenols and β-Dicarbonyl Compounds: Facile Construction of Benzofurans

Preparative electrochemical synthesis is an ideal method for establishing green, sustainable processes. The major benefits of an electro-organic strategy over that of conventional chemical synthesis are the avoidance of reagent waste and mild reaction conditions. Here, an intermolecular cross-dehydrogenative coupling between phenols and β-dicarbonyl compounds has been developed to build various benzofurans under undivided electrolytic conditions. Neither transition metals nor external chemical oxidants are required to facilitate the dehydrogenation and dehydration processes. The key factor in success was the use of nBu4NBF4 as the electrolyte and hexafluoroisopropanol as the solvent, which play key roles in the cyclocondensation step. This electrolysis is scalable and can be used as a key step in drug synthesis. On the basis of several experimental results, the mechanism, particularly of the remarkable anodic oxidation and cyclization process, was illustrated.

Identification and characterization of potential impurities of dronedarone hydrochloride

Six potential process related impurities were detected during the impurity profile study of an antiarrhythmic drug substance, Dronedarone (1). Simple high performance liquid chromatography and liquid chromatography-mass spectrometry methods were used for the detection of these process impurities. Based on the synthesis and spectral data (MS, IR, 1H NMR, 13C NMR, and DEPT), the structures of these impurities were characterized a s 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran (impurity I); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)-benzoyl)benzofuran-5-yl)-N- (methylsulfonyl)-methanesulfonamide (impurity II); N-(2-butyl-3-(4-(3- (dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-1-chloromethanesulfonamide (impurity III); N-{2-propyl-3-[4-(3-dibutylaminopropoxy)benzoyl]benzofuran-5-yl} - methanesulfonamide (impurity IV); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy) benzoyl)benzofuran-5-yl)-formamide (impurity V); and (2-butyl-5-((3- (dibutylamino)propyl)amino)benzofuran-3-yl)(4-(3- (dibutylamino)propoxy)phenyl) methanone (impurity VI). The synthesis and characterization of these impurities are discussed in detail.