156-44-5

Basic information

• Product Name: N-[(E)-(5-nitrofuran-2-yl)methylidene]aniline
• Synonyms: Aniline, N-(5-nitrofurfurylidene)-; benzenamine, N-[(1E)-(5-nitro-2-furanyl)methylene]-; N-(5-Nitrofurfurylidene)aniline; N-[(E)-(5-Nitro-2-furyl)methylene]aniline
• CAS NO: 156-44-5
• Molecular Formula: C₁₁H₈N₂O₃
• Molecular Weight: 216.1928
• Mol File: 156-44-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 355.4°C at 760 mmHg
• Flash Point: 168.7°C
• Density: 1.27g/cm³
• Vapor Pressure: 6.42E-05mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: N-[(E)-(5-nitrofuran-2-yl)methylidene]aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(E)-(5-nitrofuran-2-yl)methylidene]aniline(156-44-5)
• EPA Substance Registry System: N-[(E)-(5-nitrofuran-2-yl)methylidene]aniline(156-44-5)

Safety Data

• Hazardous Substances Data: 156-44-5(Hazardous Substances Data)

Upstream product

• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 62-53-3 aniline 
• 114729-17-8 4-{[1-(5-Nitro-furan-2-yl)-meth-(E)-ylidene]-amino}-benzoic acid methyl ester 
• 114729-20-3 (3-Butoxy-phenyl)-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 91135-78-3 (E)-4-(((5-nitrofuran-2-yl)methylene)amino)phenol 
• 17885-51-7 5-nitro-furfural-(4-chloro-phenylimine) 
• 2666-86-6 4-methyl-N-(5-nitro-furan-2-ylmethylene)-aniline 
• 92-55-7 5-nitro-2-furfuraldehyde diacetate 

Downstream Products

• 13410-74-7 4-nitro-N-((5-nitrofuran-2-yl)methylene)benzenamine 
• 82773-58-8 N-(5-nitrofurfurylidene)-2-nitroaniline 
• 156-46-7 3-Chlor-N-(5-nitro-furfuryliden)-anilin 
• 13060-78-1 2-hydroxy-N-(5-nitrofurfurylidene)aniline 
• 103987-68-4 2-chloro-N-(5-nitro-furan-2-ylmethylene)-aniline 
• 156-45-6 N-(5-Nitro-furfuryliden)-m-toluidin 
• 103983-91-1 3-{[1-(5-Nitro-furan-2-yl)-meth-(E)-ylidene]-amino}-phenol 
• 13410-73-6 N-(5-nitrofurfurylidene)-3-nitroaniline 
• 114729-19-0 (3,5-Dinitro-phenyl)-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 93198-55-1 (3,5-Bis-trifluoromethyl-phenyl)-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amine 
• 2577-98-2 5-nitro-furfural-o-tolylimine 
• 103988-66-5 3-Brom-N-(5-nitro-furfuryliden)-anilin 
• 91635-10-8 4-Brom-N-(5-nitro-furfuryliden)-anilin 
• 103987-57-1 2-bromo-N-(5-nitro-furan-2-ylmethylene)-aniline 

Relevant articles and documents

A class of 5-nitro-2-furancarboxylamides with potent trypanocidal activity against Trypanosoma brucei in vitro

Recently, the World Health Organization approved the nifurtimox- eflornithine combination therapy for the treatment of human African trypanosomiasis, renewing interest in nitroheterocycle therapies for this and associated diseases. In this study, we have synthesized a series of novel 5-nitro-2-furancarboxylamides that show potent trypanocidal activity, ～1000-fold more potent than nifurtimox against in vitro Trypanosoma brucei with very low cytotoxicity against human HeLa cells. More importantly, the most potent analogue showed very limited cross-resistance to nifurtimox-resistant cells and vice versa. This implies that our novel, relatively easy to synthesize and therefore cheap, 5-nitro-2-furancarboxylamides are targeting a different, but still essential, biochemical process to those targeted by nifurtimox or its metabolites in the parasites. The significant increase in potency (smaller dose probably required) has the potential for greatly reducing unwanted side effects and also reducing the likelihood of drug resistance. Collectively, these findings have important implications for the future therapeutic treatment of African sleeping sickness.

SOME DATA ON THE CHEMISTRY OF 5-NITRO-2-FURALDEHYDE, V. ANILINE DERIVATIVES

UV, IR and 1H-NMR spectra of Schiff bases of 5-nitro-2-furaldehyde with mono- and disubstituted anilines have been investigated.The spectra measured in methanol, in acidic and basic media and in concentrated sulfuric acid are discussed in conne

The Reaction of Aniline with 5-Nitro-2-furaldehyde. A Model for Non-Enzymic Browning Reactions

The condensation between 5-nitro-2-furaldehyde and aniline, a model for food browning reactions, yields the corresponding Schiff base, 5-nitro-2-furfurylideneaniline, cleanly.The corresponding reaction with 2-furaldehyde itself yields, in contrast, a mixture of products.Since the equilibrium constant for formation of the Schiff base from 5-nitro-2-furaldehyde and aniline, 177 dm3mol-1, is not large enough to drive the reaction to completion at moderate concentrations of aniline, phenylhydrazine was employed to trap the Schiff base as it was formed: that is, the reaction with aniline was studied by examining aniline-catalysed phenylhydrazone formation.