13663-59-7

Basic information

• Product Name: N-CYCLOHEXYL-4-NITROANILINE
• Synonyms: Cyclohexylamine,N-(p-nitrophenyl)- (6CI,7CI,8CI); N-(4-Nitrophenyl)cyclohexylamine;N-Cyclohexyl-p-nitroaniline
• CAS NO: 13663-59-7
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.27
• Mol File: 13663-59-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-CYCLOHEXYL-4-NITROANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CYCLOHEXYL-4-NITROANILINE(13663-59-7)
• EPA Substance Registry System: N-CYCLOHEXYL-4-NITROANILINE(13663-59-7)

Safety Data

• Hazardous Substances Data: 13663-59-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
N-CYCLOHEXYL-4-NITROANILINE is used as a chemical intermediate for the production of dyes, pigments, and pharmaceuticals. Its unique structure allows it to be a versatile building block in the synthesis of a wide range of compounds.
Used in Organic Synthesis:
N-CYCLOHEXYL-4-NITROANILINE is utilized in organic synthesis as a precursor for the production of other important chemical compounds. Its presence in various chemical reactions contributes to the formation of complex organic molecules.
Used in Pharmaceutical Industry:
As a chemical intermediate, N-CYCLOHEXYL-4-NITROANILINE plays a role in the development of pharmaceuticals. Its properties make it a valuable component in the synthesis of drugs with potential therapeutic applications.

Upstream product

• 114274-09-8 4-(Cyclohexylamino)-1,2,4-triazole 
• 98-95-3 nitrobenzene 
• 734-25-8 N-(4-nitrophenyl)-4-methylbenzenesulfonamide 
• 108-93-0 cyclohexanol 
• 108-91-8 cyclohexylamine 
• 111015-93-1 1-(4-nitrophenyl)-3,5-dinitro-2-pyridone 
• 108-94-1 cyclohexanone 
• 100-01-6 4-nitro-aniline 
• 586-78-7 para-nitrophenyl bromide 
• 110-83-8 cyclohexene 
• 24067-17-2 4-nitrophenylboronic acid 
• 636-98-6 p-nitrobenzene iodide 
• 766-93-8 N-cyclohexylformamide 
• 905718-45-8 [(4-nitrophenyl)(phenyl)iodonium trifluoromethanesulfonate] 

Downstream Products

• 855928-69-7 acetic acid-(N-cyclohexyl-4-nitro-anilide) 
• 857610-31-2 N,N'-dicyclohexyl-N,N'-bis-(4-nitro-phenyl)-adipamide 

Relevant articles and documents

Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides

A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.

Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions

A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.

Functional ion liquid method for catalytic synthesis of amine compounds

The invention discloses a method for synthesizing an amine compound catalyzed by functionalized ionic liquid. According to the method, functionalized ionic liquid is used as a catalyst to catalyze N-alkylation of amine and alcohol to synthesize corresponding compound derivatives. Acid functionalized ionic liquid is used as the catalyst to synthesize a series of compounds of amine. The method has the following advantages: a catalytic system is a metal-free system; the usage amount of the catalyst is small, and the catalyst has high catalytic activity, good stability and low corrosivity; operation is simple, and reaction is mild; post-treatment is easy, and the catalyst can be cyclically used.

The copper-nicotinamide complex: Sustainable applications in coupling and cycloaddition reactions

The crystalline copper(ii)-nicotinamide complex, synthesized via simple mixing of copper chloride and nicotinamide solution at room temperature, catalyzes the C-S, C-N bond forming and cycloaddition reactions under a variety of sustainable reaction conditions.

Carbon-coated magnetic palladium: Applications in partial oxidation of alcohols and coupling reactions

A carbon-coated magnetic Pd catalyst has been synthesized via in situ generation of nanoferrites and incorporation of carbon from renewable cellulose via calcination; the catalyst can be used for oxidation of alcohols, amination reaction and arylation of aryl halides (cross-coupling reaction). the Partner Organisations 2014.

Magnetic silica supported copper: A modular approach to aqueous Ullmann-type amination of aryl halides

One-pot synthesis of a magnetic silica supported copper catalyst has been described via in situ generated magnetic silica (Fe3O 4@SiO2); the catalyst can be used for the efficacious amination of aryl halides in aqueous medium under microwave irradiation.

A recyclable Cu-catalyzed C-N coupling reaction in water and its application to synthesis of imidazo[1,2-a]quinoxaline

Polystyrene-supported pyrrole-2-carbohydrazide (PSP) was synthesized and combined with CuI to make up a recyclable heterogeneous catalytic system for Ullmann-type C-N coupling reaction in water. In which, a variety of functionalized aryl halides animated efficiently with anilines, benzylamine, aliphatic amines, and imidazole. its preliminary application resulted in a more practical synthesis of imidazo[1,2-a]quinoxaline.

Sulfonic acid-functionalized ionic liquids as metal-free, efficient and reusable catalysts for direct amination of alcohols

A series of sulfonic acid-functionalized (SO3H-functionalized) ionic liquids was synthesized and used as metal-free, highly selective and efficient catalysts for the direct amination of alcohols. Notably, the activities of the series of SO3H-functionalized ionic liquids were compared and a 92% isolated yield was obtained using 3-tetradecyl-1-(butyl-4- sulfonyl)imidazolium trifluoromethanesulfonate ([BsTdIM][OTf]) as the catalyst. Importantly, the catalytic system has wide substrate scope including benzylic, allyl, propargylic, aliphatic alcohols with sulfonamide, amide, carbamate, aromatic amine and N-heterocyclic compounds. Interestingly, the system was also suitable for a multi-gram scale direct amination of alcohols. Additionally, the reusable nature of [BsTdIM][OTf] makes this protocol more attractive and avoids the disposal and neutralization of acidic catalysts. Moreover, preliminary experiments indicated that this reaction should proceed via an SN1 pathway. Copyright

New ligands for copper-catalyzed C-N coupling reactions with aryl halides

2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-containing heterocycles under mild conditions. The catalytic system showed great functional-group tolerance and excellent chemoselectivity. 7copy; 2012 Elsevier Ltd. All rights reserved.

OXIDATIVE HOMO-COUPLING REACTIONS OF ARYL BORONIC ACIDS USING A POROUS COPPER METAL-ORGANIC FRAMEWORK AS A HIGHLY EFFICIENT HETEROGENEOUS CATALYST

The disclosure provides methods for the use of open metal frameworks to synthesize biaryls comprising contacting a metal organic framework (MOF) or metal organic polyhedral (MOP) with an aryl boronic acid compound under conditions wherein the MOF or MOP catalyze the synthesis of the biaryl through a homo-coupling reaction.