1132-38-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
N-cyclohexylideneaniline is used as an intermediate in the synthesis of various organic compounds, particularly in the production of pharmaceuticals and agrochemicals. Its unique structure allows it to be a key component in the development of new drugs and agricultural chemicals, contributing to advancements in these fields.
Used in Dyes and Pigments Industry:
N-cyclohexylideneaniline is also employed as a building block for the preparation of dyes and pigments. Its ability to form stable compounds with other chemical entities makes it a valuable resource in creating a wide range of colors and shades for various applications, including textiles, plastics, and printing inks.
As a Hazardous Substance:

Upstream product

• 108-94-1 cyclohexanone 
• 62-53-3 aniline 
• 108-93-0 cyclohexanol 
• 1821-36-9 N-phenyl-2-cyclohexylamine 
• 1227476-15-4 Azobenzene 
• 622-37-7 Phenyl azide 
• 110-83-8 cyclohexene 
• 1670-47-9 1,1-diethoxycyclohexane 
• 64269-06-3 1-(phenylamino)cyclohexanecarbonitrile 
• 108-91-8 cyclohexylamine 
• 2201-24-3 1-phenylcyclohexylamine 
• 2325-27-1 N-phenyltriphenyliminophosphorane 
• 98-95-3 nitrobenzene 
• 100-64-1 cyclohexanone-oxime 

Downstream Products

• 80254-41-7 1,3-diphenyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4-dithione 
• 38425-88-6 3-(2-phenylimino-cyclohexyl)-propionitrile 
• 57178-09-3 4?phenyl?1?thia?4?azaspiro[4.5]decan?3?one 
• 69139-51-1 4-(1'-oxo-2'-phenyl-1',4'-dihydro-2'H-spiro[cyclohexane-1,3'-isoquinoline]-4'-carbonyl)-morpholine 
• 93994-44-6 N-Phenyl-N'-(4-chlor-benzolsulfonyl)-C-cyclopentyl-formamidin 
• 5785-79-5 (C₃H₇)2BN(C₆H₅)C₆H₉ 
• 59631-53-7 2-Isopropyl-3,3-dimethyl-thiobutyranilid 
• 124841-84-5 O,O-dibutyl(1-phenylaminocyclohexyl)phosphonate 
• 19973-12-7 1-phenyl-3,4,5,6,7,8-hexahydro-1H-quinolin-2-one 
• 77229-09-5 N-phenyl-2,3,5,6,7,8-hexahydro-4-quinolinone 
• 7236-86-4 diethyl (1-(phenylamino)cyclohexyl)phosphonate 
• 124841-87-8 cyclohexylphenylimine hydrochloride 
• 77243-09-5 3-methyl-N-phenyl-3,4,5,6,7,8-hexahydro-2-quinolinone 
• 77229-06-2 4-methyl-N-phenyl-3,4,5,6,7,8-hexahydro-2-quinolinone 

Relevant academic research and scientific papers

Reductive amination of aldehydes and ketones with sodium borohydride supported onto HZSM-5 zeolite under microwave irradiation in a solvent free system

Sodium borohydride supported onto a HZSM-5 zeolite is presented as a general reducing agent for the reductive amination of aldehydes and ketones under microwave irradiation in solventless system. Copyright Taylor & Francis Inc.

The azaallylic anion as a synthon for Pd-catalyzed synthesis of heterocycles: domino two- and three-component synthesis of indoles

(Chemical Equation Presented) Piecing it all together with palladium: Two- and three-component cascade processes that are promoted by a multifunctional Pd catalyst lead to indoles in a highly efficient manner (see scheme). The key step is the Pd-catalyzed α-arylation of imines with o-dihalobenzene derivatives.

Three-Component Cascade Reactions with 2,3-Diketoesters: A Novel Metal-Free Synthesis of 5-Vinyl-pyrrole and 4-Hydroxy-indole Derivatives

5-Vinyl-pyrrole and 4-hydroxy-indole derivatives are synthesized by metal-free aldol/cyclization/aromatization cascade reactions of in situ generated enamines with 2,3-diketoesters. This convenient atom-economical process produces multifunctional pyrrole and indole products in moderate to good yields.

Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4

An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant

Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is

Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media

Abstract: A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity. Graphic abstract: A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni nanocatalyst.[Figure not available: see fulltext.]

Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor

Reductive amination of aldehydes and ketones with primary and secondary amines under catalysis with nickel nanoparticles supported on zeolite X, MgO, or activated carbon in the gas phase or in the gas-liquid system in a plug-flow reactor proceeds at atmospheric pressure of hydrogen with the formation of secondary or tertiary amines in high yield.

Metal-free nitrogen -doped carbon nanosheets: A catalyst for the direct synthesis of imines under mild conditions

Herein, a highly stable, porous, multifunctional and metal-free catalyst was developed, which exhibited significant catalytic performance in the oxidation of amines and transfer hydrogenation of nitriles under mild conditions; this could be attributed to the presence of numerous active sites and their outstanding BET surface area. The obtained results showed that most of the yields of imines exceeded 90%, and the cycling performance of the catalyst could be at least seven runs without any decay in the reaction activity, which could be comparable to those of metal catalysts. Subsequently, a kinetic study has demonstrated that the apparent activation energy for the direct synthesis of imines from amines is 67.39 kJ mol-1, which has been performed to testify that the catalytic performances are rational. Via catalyst characterizations and experimental data, graphitic-N has been proven to be the active site of the catalyst. Hence, this study is beneficial to comprehend the mechanism of action of a metal-free N-doped carbon catalyst in the formation of imines.

Oxidative Rearrangement of Primary Amines Using PhI(OAc)2 and Cs2CO3

An oxidative rearrangement of primary amines mediated by a hypervalent iodine(III) reagent is herein reported. The combination of PhI(OAc)2 and Cs2CO3 proves highly efficient at inducing the direct 1,2-C to N migration of primary amines, which can be applied to the preparation of both acyclic and cyclic amines. A mechanistic study shows that the rearrangement proceeds via a concerted mechanism.