1821-36-9

Usage

Uses

Used in Chemical Synthesis:
N-Cyclohexylaniline is used as a reagent in palladium-catalyzed amination of aromatic bromides. This reaction is an important method for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Cyclohexylaniline is used as a building block for the synthesis of various drug molecules. Its unique structure allows for the formation of diverse chemical entities with potential therapeutic applications.
Used in Agrochemical Industry:
N-Cyclohexylaniline is also used in the agrochemical industry for the synthesis of active ingredients in pesticides and herbicides. Its reactivity and compatibility with various chemical groups make it a valuable intermediate in the development of new agrochemical products.
Used in Specialty Chemicals:
In the specialty chemicals sector, N-Cyclohexylaniline is employed as a precursor for the synthesis of various functional materials, such as dyes, pigments, and polymers. Its versatility in chemical reactions enables the creation of a wide range of specialty products with specific properties and applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1927, 1985 DOI: 10.1021/jo00211a028Synthetic Communications, 19, p. 565, 1989Tetrahedron Letters, 16, p. 119, 1975

InChI:InChI=1/C12H17N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1,3-4,7-8,12-13H,2,5-6,9-10H2

Upstream product

• 54955-24-7 N-cyclohexyl-N-nitrosoaniline 
• 108-94-1 cyclohexanone 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 103-70-8 Formanilid 
• 108-86-1 bromobenzene 
• 108-91-8 cyclohexylamine 
• 122-39-4 diphenylamine 
• 108-85-0 1-bromocyclohexane 
• 542-18-7 cyclohexyl chloride 
• 142-04-1 aniline hydrochloride 
• 110-83-8 cyclohexene 
• 108-93-0 cyclohexanol 
• 873-51-8 phenylborondichloride 

Downstream Products

• 4212-82-2 N-cyclohexyl-acetanilide 
• 110-83-8 cyclohexene 
• 56418-80-5 N-cyclohexyl-N-ethylaniline 
• 4705-13-9 N-cyclohexyl-N-phenylaniline 
• 93995-78-9 N-cyclohexyl-4-phenylazo-aniline 
• 86-74-8 9H-carbazole 
• 94593-61-0 N-cyclohexylbenzanilide 
• 2933-12-2 N,N-diethyl-N'-cyclohexyl-N'-phenyl-ethylenediamine 
• 100721-33-3 2-chloro-N-cyclohexyl-N-phenylacetamide 
• 1454-79-1 N-cyclohexyl-4-methyl-N-phenylbenzenesulfonamide 
• 100951-07-3 3-chloro-propionic acid-(N-cyclohexyl-anilide) 
• 18707-43-2 N-cyclohexyl-N-methylaniline 
• 101269-84-5 cyclohexyl-phenyl-carbamic acid-(3-chloro-propyl ester) 
• 25761-73-3 N-cyclohexyl-N-phenylcarbamoyl chloride 

Relevant academic research and scientific papers

Synthesis and characterization of bidentate NHC-Pd complexes and their role in amination reactions

The new well-defined and air-stable ortho-xylyl-linked N-heterocyclic carbene (NHC) Pd complexes (2a-d) have been synthesized and characterized by elemental analysis, 1H NMR, 13C NMR, IR spectroscopy, and single crystal X-ray diffraction studies. The palladium atom in the complex 2a lies on a crystallographic mirror plane and can be described as having a square-planar coordination environment with the carbene atoms of the benzimidazole rings of the ligand occupying two coordination sites in cis positions. Two further coordination sites are occupied by chloride ligands. The benzimidazole rings are connected to each other by an ortho-xylyl bridge. The catalytic activity of these palladium complexes has been tested in the coupling reactions of various N-containing substrates with bromobenzene. A preliminary catalytic study shows that the bis(NHC)-Pd complexes are highly active in the Buchwald-Hartwig amination reaction.

Reduction of imines to amines through use of Cp2MoH2 and protonic acid system

Imines are conveniently reduced to the corresponding amines by molybdenum dihydride CpMoH2 under mild conditions in good yields.In the presence of a ketone only an imine was reduced and the ketone was recovered quantitatively.

THE ACTUAL MERCURATING SPECIES IN THE MERCURATION OF AROMATIC AMINES AND THE AMINOMERCURATION OF OLEFINS

The reactivity of ?- and ?- N-mercurated and C-mercurated amines as electrophiles towards olefins and aromatic amines is studied under different reaction conditions.Depending on the ionic or covalent character of the starting mercury(II) salt, dissociated

Highly Coordinated Tin Hydrides: A Novel Synthesis of Tertiary Amines via Hydrostannation of Imines

The highly coordinated tin hydride, Bu2SnClH-HMPA (B), is shown to be an effective agent for the reduction of imines.The subsequent alkylation of the resulting intermediate tin amides permitted the preparation of a series of tertiary amines in a one-pot procedure.The spectral identification of the novel tin hydrides, B and Bu2SnClH-Bu4NF, was accomplished by 1H, 13C, and 119Sn NMR and FT-IR studies.

ELECTROLYTIC BEHAVIOR OF TETRASUBSTITUTED IMINIUM SALT IN ACETONITRILE.

Cathodic behavior of N-cyclohexylidenepyrrolidinium salt (1) and N-cyclohexylideneaniline (2) in acetonitrile has been studied by means of dc polarography, cyclic voltammetry and preparative electrolysis under controlled potential conditions. Compound 1 e

Synthesis of palladium complexes derived from imidazolidin-2-ylidene ligands and used for catalytic amination reactions

N-Aryl amination and the Buchwald–Hartwig reaction are of great synthetic and industrial interest and scientists accept their usefulness and versatility for obtaining arylamines. In this study Ag–N-heterocyclic carbene complexes were used as transmetallation reagents for the synthesis of Pd–N-heterocyclic carbene complexes. The new Pd–N-heterocyclic carbene complexes were characterized using elemental analysis and 1H NMR, 13C NMR and infrared spectroscopies. The crystal structure of one, namely dichlorobis[1,3-bis(2-methylbenzyl)imidazolidin-2-yliden]palladium(II), is presented. The activity of the Pd(II) complexes in the coupling reaction of anilines or amines with bromobenzene was investigated. These complexes exhibited high catalytic activities in the direct synthesis of triarylamines and secondary amines in a single step. Copyright

Oxidative three-component carboamination of vinylarenes with alkylboronic acids

The three-component carboamination of alkenes is of significant interest due to the ease by which functionalized amines can be produced from readily available chemical building blocks. Previously, a variety of carbon-centered radical precursors have been

The impact of the nature of amine reactants in the palladium catalyzed conversion of phenol to N-substituted anilines

Anilines and cyclohexylamines are currently produced from fossil feedstocks. Phenol would be an attractive alternative feedstock that can be obtained from renewable resources. We herein clarify the influence of the amine on the course of the amination of phenol using a hydrogen borrowing strategy. Amines can in this case act as a reductant which can be dehydrogenated to initiate the partial hydrogenation of phenol which is required for the reaction to take place. The nature of the amine reactant can have a larger effect than the presence of additional reductants like sodium formate. The results in this report do not only present a method for the amination of phenol without addition of an extra reductant, but also rationalize the reactivity of amines in their reaction with phenol.

Visible-light-mediated tungsten-catalyzed C-H amination of unactivated alkanes with nitroarenes

Alkylamines are important motifs in pharmaceutical and material sciences. The existing reports of C-H amination are limited to ammonia, diazo and azide nitrogen sources. This work describes a rapid construction of C-N bonds from accessible nitroarene and alkane feedstock under decatungstate catalysis. A variety of C-H precursors including gaseous, linear, cyclic and benzylic hydrocarbons could adopt this protocol to afford the corresponding alkylamines in high efficiency. [Figure not available: see fulltext.]

A base-free Chan–Lam reaction catalyzed by an easily assembled Cu(II)-carboxylate metal-organic framework

A new copper(II) metal-organic framework is constructed as a sustainable copper heterogeneous catalyst. Cu-DPTCA, with high catalytic activity, can effectively promote the Chan–Lam coupling reaction of arylboronic acids and amines without adding any base or additive.