137832-14-5

Basic information

• Product Name: (E)-N-(4-nitrobenzyl)-1-(4-nitrophenyl)methanimine
• Synonyms: (E)-N-(4-nitrobenzyl)-1-(4-nitrophenyl)methanimine
• CAS NO: 137832-14-5
• Molecular Weight: 285.259
• Mol File: 137832-14-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-N-(4-nitrobenzyl)-1-(4-nitrophenyl)methanimine(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N-(4-nitrobenzyl)-1-(4-nitrophenyl)methanimine(137832-14-5)
• EPA Substance Registry System: (E)-N-(4-nitrobenzyl)-1-(4-nitrophenyl)methanimine(137832-14-5)

Safety Data

• Hazardous Substances Data: 137832-14-5(Hazardous Substances Data)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 7409-30-5 p-nitrobenzylamine 
• 18600-42-5 4-nitrobenzylamine hydrochloride 
• 100872-24-0 benzylidene-(4-nitro-benzyl)-amine 
• 126178-30-1 N-(4-nitrobenzylidene)-1-phenylmethanamine 
• 64-17-5 ethanol 

Downstream Products

• 555-16-8 4-nitrobenzaldehdye 

Relevant articles and documents

Base-Mediated Generation of Ketenimines from Ynamides: [3+2] Annulation with Azaallyl Anions

Under basic conditions and heat, ynamides can serve as precursors to ketenimines, whose synthetic potential is often hampered by their difficulty of access. Herein, we report that they can undergo a [3+2] cycloaddition with 2-azaallyl anions, obtained from benzylimines under the same reaction conditions. This reaction between two highly reactive intermediates, both generated in situ from bench stable starting materials, gives access to various nitrogen-rich heterocycles. The reaction usually proceeds with excellent diastereoselectivity, in favor of the cis adduct. Deuteration experiments and DFT calculations helped rationalize the regio- and stereoselectivity of the process as well as the formation of side products. (Figure presented.).

Reactions of Benzylamine and Selected Ring- and N-Substituted Derivatives with Iodine, Including a Synthesis for Benzonitriles

Benzylamine and its ring-substituted derivatives are smoothly dehydrogenated to iminium ions by iodine in a non-nucleophilic polar solvent such as acetonitrile.If excess amine is used, condensation of the iminium ion with free benzylamine occurs, affording N-benzylidenebenzylamines.However, when t-butylamine is present as a co-solvent, further dehydrogenation takes place and good to excellent yields of benzonitriles are obtained.N-Monosubstituted benzylamines are converted to N-benzylidene amines which, in the presence of t-butylamine, undergo transamination forming N-benzylidene-t-butylamine.In acetonitrile, the iminium species resulting from N-methylbenzylamine condenses with two molecules of free amine to give N,N'-dibenzyl-N,N'-dimethyl-1-phenylmethanediamine.Treatment of N-methylbenzylamine with iodine in the presence of alcohols as co-solvents leads to the formation of acetals in low yields.N,N-Disubstituted benzylamines form tertiary iminium ions which undergo hydrolysis on aqueous workup., liberating benzaldehyde and the appropriate secondary amine fragment.In the presence of t-butylamine, N-benzylidene-t-butylamine is once again obtained.Probable mechanisms for these reactions are outlined.