10480-05-4

Basic information

• Product Name: 4-nitro-N-[(E)-(4-nitrophenyl)methylidene]aniline
• Synonyms: 4-Nitro-N-[(E)-(4-nitrophenyl)methylene]aniline; benzenamine, 4-nitro-N-[(1E)-(4-nitrophenyl)methylene]-
• CAS NO: 10480-05-4
• Molecular Formula: C₁₃H₉N₃O₄
• Molecular Weight: 271.2283
• Mol File: 10480-05-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 479.8°C at 760 mmHg
• Flash Point: 244°C
• Density: 1.35g/cm³
• Vapor Pressure: 6.68E-09mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 4-nitro-N-[(E)-(4-nitrophenyl)methylidene]aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitro-N-[(E)-(4-nitrophenyl)methylidene]aniline(10480-05-4)
• EPA Substance Registry System: 4-nitro-N-[(E)-(4-nitrophenyl)methylidene]aniline(10480-05-4)

Safety Data

• Hazardous Substances Data: 10480-05-4(Hazardous Substances Data)

Upstream product

• 619-73-8 4-nitrobenzyl chloride 
• 100-01-6 4-nitro-aniline 
• 100-46-9 benzylamine 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 58825-56-2 2,3-bis-(4-nitro-phenyl)-6-trifluoromethyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 40046-78-4 2,3-bis-(4-nitro-phenyl)-6-phenyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 76086-93-6 3-[(4-Nitro-phenyl)-(4-nitro-phenylamino)-methyl]-1,3-dihydro-indol-2-one 
• 111536-94-8 3-phenyl-4,5-bis(p-nitrophenyl)-4,5-dihydro-1,2,4-oxadiazol 
• 14429-15-3 4-nitro-N-(4-nitrobenzyl)benzenamine 
• 126178-30-1 N-(4-nitrobenzylidene)-1-phenylmethanamine 
• 785-80-8 p-nitrobenzylideneaniline 
• 25105-60-6 2,3,6,7-tetrahydro-3-isopropyl-2-(4-nitrophenyl)cyclo-penta[e][1,3]oxazin-4(5H)-one 
• 58825-61-9 1-(4-Nitro-phenyl)-3-(2,2,2-trifluoro-acetyl)-urea 
• 555-16-8 4-nitrobenzaldehdye 
• 3646-57-9 bis(4-nitrophenyl)diazene 

Relevant articles and documents

Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl imines

A series of aryl imines have been synthesized by Fly-ash: H 2SO4 catalyzed microwave assisted process under solvent-free conditions. The yields of the imines have been found to be more than 87%. The purity of all imines has been checked using their physical constants and spectral data as published earlier in literature. The UV λmaxCN(nm), infrared νCN(cm-1), NMR δ(ppm) of CH and CN spectral data have been correlated with Hammett substituent constants and F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the above spectral data has been studied. The antimicrobial activities of All synthesised imines have been studied using Bauer-Kirby method.

Reactions of HDDA Benzynes with C,N-Diarylimines (ArCH=NAr')

o-Benzynes can be utilized to construct heterocyclic motifs using various nucleophilic and cycloaddition trapping reactions. Acridines have been synthesized by capture of C,N-diarylimines with benzynes generated by classical methods (i.e., from ortho-elimination of precursor arene compounds), although in poor yields. We report here that these imines can be trapped by benzynes generated by the hexadehydro-Diels–Alder (HDDA) reaction in an efficient manner to produce 1,4-dihydroacridine products. These dihydroacridines were subsequently aromatized using MnO2 to provide structurally complex acridines.

Direct synthesis of unsaturated β-amino acids

Zinc bromide promoted addition of trimethylsilyl butenoate lithium enolates to aromatic aldimines. The corresponding β-amino acids were obtained in moderate to good yields as anti isomers. The reaction was believed to proceed via the zinc enolates. A tentative explanation of the selectivity in favour of the anti isomers was proposed.

Aerobic oxidation of amines to imines catalyzed by a ruthenium complex under solvent-free conditions

A ruthenium complex [Et3NH]2[Ru(dipic)Cl3] showed high efficiency in the homo-coupling of primary amines and cross-coupling of benzylamine with anilines and aliphatic amines to the corresponding imines under air and solvent-free conditions. This protocol is an atom-economical green process and tolerates various substrates bearing both electron-donating and electron-withdrawing substituents.

Oxidation of aromatic anils by sodium perborate in aqueous acetic Acid Medium

The kinetics of oxidation of 9 meta- and 15 para- substituted aromatic anils by sodium perborate were investigated in aqueous acetic acid medium. The reaction was second order with respect to aromatic anil and first order with respect to the sodium perborate. The increase of [H+] in this oxidation retards the rate of the reaction. The observed rate constant for the substituents were plotted against the Hammett constant, δ and a non-linear concave downward curve was obtained for the anils with substituents in the aniline moiety. The observed break in the log kobs versus δwas attributed to the transition state whereas the non-linear concave upward curve was observed for the substituents in the benzaldehyde moiety and a non-linear concave upward curve was observed for the substituents in the combination of aniline and benzaldehyde moiety. The electron withdrawing substituents fall on one side of the curve, having a negative ρvalue and the electron releasing substituents fall on the other side, with a positive ρvalue and a suitable mechanism was proposed.