141645-23-0

Basic information

• Product Name: (2-Butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone
• Synonyms: (2-Butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone;(2-butyl-5-nitrobenzofuran-3-yl)(4-(3-(dibutylaMino)propoxy)phenyl)Methanone;4-[(2-butyl-6-nitro-1-benzofuran-3-yl)carbonyl]phenol;2-butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylaMino)propoxy]phenyl]-;Methanone, (2-butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylaMino)propoxy]phenyl]-;2-Butyl-3-[4-(2-Dibutylaminopropoxy)benzoyl]-5-Nitrobenzofuran;Dronedarone Impurity D;(2-butyl-5-nitro-1-benzofuran-3-yl)-[4-[3-(dibutylamino)propoxy]phenyl]methanone
• CAS NO: 141645-23-0
• Molecular Formula: C₃₀H₄₀N₂O₅
• Molecular Weight: 508.65
• EINECS: 1806241-263-5
• Product Categories: API
• Mol File: 141645-23-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 638.148 °C at 760 mmHg
• Flash Point: 339.74 °C
• Appearance: Off-white crystalline
• Density: 1.109
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.56
• PKA: 9.43±0.50(Predicted)
• CAS DataBase Reference: (2-Butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2-Butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone(141645-23-0)
• EPA Substance Registry System: (2-Butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone(141645-23-0)

Safety Data

• Hazardous Substances Data: 141645-23-0(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2-Butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone" is a complex molecule with a long chain structure. It consists of a benzofuranyl ring with a butyl and nitro group attached, as well as a phenylmethanone group connected to a dibutylamino propoxy chain. (2-Butyl-5-nitro-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone is used in pharmaceutical research and has potential applications in drug development, particularly in the areas of cardiovascular and central nervous system disorders. Its specific properties and potential uses would require further research and testing.

InChI:InChI=1/C30H40N2O5/c1-4-7-11-28-29(26-22-24(32(34)35)14-17-27(26)37-28)30(33)23-12-15-25(16-13-23)36-21-10-20-31(18-8-5-2)19-9-6-3/h12-17,22H,4-11,18-21H2,1-3H3

Upstream product

• 114980-27-7 4-<3-(dibutylamino)propoxy>benzaldehyde 
• 772-33-8 Koshlands reagent I 
• 20120-23-4 3-dibutylaminopropionic acid ethyl ester 
• 111-92-2 dibutylamine 
• 540-38-5 p-Iodophenol 
• 89487-91-2 2-iodo-4-nitrophenol 
• 2050-51-3 3-dibutylaminopropanol 
• 33527-94-5 4-acetoxyiodobenzene 
• 1636167-45-7 2-(hex-1-yn-1-yl)-4-nitrophenyl acetate 
• 504421-91-4 2-iodo-4-nitrophenyl acetate 
• 141645-16-1 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran 
• 1356411-44-3 C₃₀H₄₃N₃O₅ 
• 115555-77-6 1-chloro-3-(di-n-butylamino)-propane hydrochloride 
• 1333493-60-9 1-{4-[3-(di-n-butylamino)propoxy]phenyl}-1,3-heptanedione hydrochloride 

Downstream Products

• 141626-36-0 dronedarone 
• 141626-57-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)-benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide 
• 141625-93-6 dronedarone hydrochloride 
• 500791-70-8 5-amino-2-n-butyl-3-[4-(3-di-n-butylamino propoxy)benzoyl]benzofuran bisoxalate 
• 1278585-69-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)acetamide 
• 1354567-98-8 2-n-butyl-3-{4-[3-(di-n-butylamino)propoxy]benzoyl}-5-aminobenzofuran hydrochloride 
• 1354567-97-7 N-[2-butyl-3-[4-(3-(di-n-butylamino)propoxy)benzoyl]-5-benzofuranyl]methanesulfonamide hydrobromide 
• 141644-91-9 (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-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.

Concise total synthesis of antiarrhythmic drug dronedarone via a conjugate addition followed intramolecular heck cyclization

A concise, scalable, and an efficient total synthesis for dronedarone (2) was described using conjugate addition followed by intramolecular Heck cyclization. The other key reaction includes selective reduction of nitro functionality and addition of lithiated terminal alkyne to the aldehyde. The overall yield of this approach is 44% in six steps.

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.