67490-46-4

Usage

Chemical compound

Benzenemethanimine, 4-nitro-

Also known as

p-nitrobenzylamine

Physical properties

Pale yellow crystalline substance

Functional group

Nitro group attached to benzene ring

Uses

Organic synthesis, pharmaceutical research, intermediate in production of dyes and pharmaceuticals

Safety

Considered hazardous, should be handled and stored with care, follow proper safety protocols

Upstream product

• 110-91-8 morpholine 
• 114467-15-1 C₁₃H₁₁N₂O₅S*H⁽¹⁺⁾ 
• 114467-13-9 C₁₃H₁₀BrN₂O₅S*H⁽¹⁺⁾ 
• 114467-12-8 C₁₃H₁₀N₃O₇S*H⁽¹⁺⁾ 
• 114467-11-7 C₁₄H₁₀F₃N₂O₅S*H⁽¹⁺⁾ 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 13889-98-0 N-acetylpiperidine 
• 555-16-8 4-nitrobenzaldehdye 
• 7409-30-5 p-nitrobenzylamine 

Downstream Products

• 56841-81-7 4-nitrobenzalchloroimine 
• 23980-86-1 3-(4-nitrobenzylideneamino)quinoline 
• 13707-46-5 N-tosyl-4-nitrobenzaldimine 
• 1093111-99-9 3-methylene-5-(4-nitro-phenyl)-pyrrolidin-2-one 

Relevant academic research and scientific papers

A practical oxidative conversion of aldehydes into N-chloroaldimines

A novel method for the preparation of N-chloroaldimines from commonly available aromatic aldehydes has been developed. The reaction proceeded effectively by two steps: aldehydes were initially transformed into imines and then chloro-substitution with NaClO2 gave the N-chloroaldimines. This simple protocol allows for the preparation of a variety of aromatic N-chloroaldimines in moderate to excellent yields without the isolation of the imine intermediate. We also found that 3-nitrobenzaldehyde and 4-cyanobenzaldehyde were converted into the related benzonitrile directly under the standard conditions.

Synthesis, photophysical and acidochromic properties of a series of tetrahydrodibenzo[a,i]phenanthridine chromophores

A series of luminescent 5-aryl-tetrahydrodibenzo[a,i]phenanthridines was developed through modified synthetic protocol using SnCl2-acetic acid as a catalyst. The synthesis was consistent with various functionalities and significantly improves t

Imine allylation using 2-alkoxycarbonyl allylboronates as an expedient three-component reaction to polysubstituted α-exo-methylene-γ-lactams

α-exo-Methylene-γ-lactams are key structural units in a wide variety of biologically active natural products. A concise route to the formation of polysubstituted α-exo-methylene-γ-lactams is described. In this three-component reaction, an imine is formed

Synthesis of some 2-aminonitroethanes via tin(II)chloride mediated addition reaction of bromonitromethane to imines

In the presence of tin(II)chloride, bromonitromethane reacts with imines derived from aromatic aldehydes and ammonia to yield 2-amino-2-aromatic substituted nitroethane derivatives via an addition reaction in good yields.

Correlation analysis of reactivity in the oxidation of substituted benzylamines by pyridinium hydrobromide perbromide

The oxidation of benzylamine and twenty-seven ortho-, meta- and para-substituted benzylamines by pyridinium hydrobromide perbromide (PHPB), in dimethylsulphoxide (DMSO), leads to the formation of the corresponding aldimines. The reactions are of first order with respect to both PHPB and the amine. The oxidation of deuterated benzylamine exhibited a substantial kinetic isotope effect (kII/kD = 3.20 at 303 K). An addition of pyridinium bromide does not affect the rate. PHPB itself has been postulated as the reactive oxidizing species. The rates of the oxidation of para- and meta-substituted benzylamines were correlated with Taft's and Swain's field and resonance substituent constants. The oxidation of para-substituted benzylamines showed an excellent correlation with Taft's σI and σRBA values; the meta-compounds correlated best with σI and σR0 values. Rates of the ortho-substituted compounds showed a significant correlation with Charton's triparametric equation. Suitable mechanism has been proposed.

Kinetics and mechanism of the oxidation of substituted benzylamines by oxo(salen)manganese(V) complexes

The oxidation of substituted benzylamines by substituted oxo(salen)manganese(V) complexes, in acetonitrile, leads to the formation of the corresponding aldimines. The reaction is first order with each of the amine and the Mn(V) complex. The oxidation of [1,1-2H2]benzylamine exhibited the presence of substantial kinetic isotope effects. The rates of oxidation of 19 amines by 4 Mn(V) complexes have been determined. Correlation analyses of the rates of oxidation of the 19 monosubstituted benzylamines were performed with various single and multiparametric equations. The rates of the oxidation showed excellent correlations in terms of Yukawa-Tsuno and Brown's equations. The polar reaction constants are negative. The rate of reduction of the substituted Mn(V) complexes showed an excellent correlation in terms of the Hammett equation with positive reaction constants. The reactivity-selectivity principle (RSP) is obeyed in this reaction. The validity of RSP was verified by Exner's mathematical procedure. Suitable mechanisms have been discussed.

Kinetics and mechanism of the oxidation of substituted benzylamines by hexamethylenetetramine-bromine

The oxidation of substituted benzylamines by hexamethylenetetramine-bromine (HABR) to the corresponding aldimines is first order with respect to each the amine and HABR. It is proposed that HABR itself is the reactive oxidizing species. The oxidation of deuterated benzylamine (PhCD2NH2) indicated a substantial kinetic isotope effect (kH/kD = 5.60 at 293 K). This confirmed the cleavage of an α-C-H bond in the rate-determining step. Correlation analyses of the rates of oxidation of 20 monosubstituted benzylamines were performed with various single-and multi-parametric equations. The rates of the oxidation showed excellent correlations in terms of the Yukawa-Tsuno and Brown equations. The polar reaction constants were negative. The oxidation exhibited extensive cross-conjugation, in the transition state, between the electron-donating substituents and the reaction centre. A mechanism involving a hydride ion transfer from the amine to HABR, in the rate-determining step, is proposed. Copyright

Correlation analysis of reactivity in the oxidation of substituted benzylamines by benzyltrimethylammonium tribromide

The oxidation of benzylamine and twenty-seven ortho-, meta- and para-monosubstituted benzylamines by benzyltrimethylammonium tribromide (BTMAB), in dimethylsulphoxide (DMSO), leads to the formation of corresponding aldimines. The reaction is first order with respect to both BTMAB and the amine. The oxidation of deuterated benzylamine exhibited a substantial kinetic isotope effect. Addition of benzyltrimethylammonium bromide does not affect the rate. Tribromide ion has been postulated as the reactive oxidizing species. The rates of the oxidation of para- and meta-substituted benzylamines showed excellent correlation in terms of both Taft's dual substituent-parameter and Charton's triparametric LDR equations, whereas the ortho-substituted compounds exhibited the best correlation with the Charton's tetraparametric LDRS equation. The oxidation of para-substituted benzylamines is more susceptible to the delocalization effect than is the oxidation of ortho- and meta-substituted compounds, which display a greater dependence on the field effect. The low positive value of the η suggests the presence of an electron-deficient centre in the rate-determining transition state with less charge separation. A suitable mechanism has been proposed.

Structural Effects on the Transition States of Imine-Forming Eliminations in N-Substituted O-(Arylsulfonyl)hydroxylamines

A series of amines with various alkyl and aryl substituents at C-1 were converted to the corresponding N-(arylsulfonoxy)amines, which served as precursors for base-promoted, imine-forming elimination.By varying the bases used to promote the elimination and by varying the leaving groups attached to nitrogen, the Broensted parameters β and βlgCH3 were determined.These were used to locate the transition state on the More O'Ferrall-Jencks energy surface for elimination.Substituents were found to influence the structure of the activated complex markedly.Resonance effects were most important, while inductive effects had little influence .