146334-66-9

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 589-91-3 p-methylcyclohexanol 
• 106-49-0 p-toluidine 
• 589-92-4 1-methylcyclohexan-4-one 
• 106-44-5 p-cresol 
• 62-53-3 aniline 
• 108-94-1 cyclohexanone 
• 51488-27-8 N-(4-methylcyclohexylidene)pyridine-3-amine 

Downstream Products

• 620-93-9 di-p-tolylamine 
• 1159-53-1 tri(p-tolyl)amine 

Relevant academic research and scientific papers

Selective primary aniline synthesis through supported Pd-catalyzed acceptorless dehydrogenative aromatization by utilizing hydrazine

By utilizing hydrazine (N2H4) as the nitrogen source in the presence of a hydroxyapatite-supported Pd nanoparticle catalyst (Pd/HAP), various primary anilines can be selectively synthesized from cyclohexanonesviaacceptorless dehydrogenative aromatization. The strong nucleophilicity of N2H4and the stability of the hydrazone intermediates can effectively suppress the formation of the undesired secondary aniline byproducts.

Selective Synthesis of Primary Anilines from NH3 and Cyclohexanones by Utilizing Preferential Adsorption of Styrene on the Pd Nanoparticle Surface

Dehydrogenative aromatization is one of the attractive alternative methods for directly synthesizing primary anilines from NH3 and cyclohexanones. However, the selective synthesis of primary anilines is quite difficult because the desired primary aniline products and the cyclohexanone substrates readily undergo condensation affording the corresponding imines (i.e., N-cyclohexylidene-anilines), followed by hydrogenation to produce N-cyclohexylanilines as the major products. In this study, primary anilines were selectively synthesized in the presence of supported Pd nanoparticle catalysts (e.g., Pd/HAP, HAP=hydroxyapatite, Ca10(PO4)6(OH)2) by utilizing competitive adsorption unique to heterogeneous catalysis; in other words, when styrene was used as a hydrogen acceptor, which preferentially adsorbs on the Pd nanoparticle surface in the presence of N-cyclohexylidene-anilines, various structurally diverse primary anilines were selectively synthesized from readily accessible NH3 and cyclohexanones. The Pd/HAP catalyst was reused several times though its catalytic performance gradually declined.

Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines

Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and tertiary substituted cyclohexylamines can be synthesized under convenient conditions in moderate to excellent yields.

A bifunctional palladium/acid solid catalyst performs the direct synthesis of cyclohexylanilines and dicyclohexylamines from nitrobenzenes

Nitroderivatives are transformed to cyclohexylanilines at room temperature in good yields and selectivity via a hydrogenation-amine coupling cascade reaction using Pd nanoparticles on carbon as a catalyst and a Broensted acid.

Catalytic Synthesis of Triarylamines

Condensation along Ullman reaction in the presence of copper catalysts was carried out with para-substituted arylamines and p-iodotoluene to yield the corresponding triarylamines. For preparation of diarylamines was used dehydrogenation of N-cycloalkylanilines and azomethines; diarylamines were obtained through dehydroamination of cycloaliphatic alcohols with anilines.

Catalytic reduction of the arene ring, and other functionalities, of organic substrates using formic acid and palladium on carbon

The arene ring in a variety of compounds with functionalities which contain nitrogen is reduced in good yields using formic acid and Pd/C in methanol.