20887-06-3

Usage

Uses

Used in Organic Synthesis:
N-(2-aminobenzyl)aniline is utilized as a key intermediate in organic synthesis for its ability to participate in various chemical reactions, facilitating the creation of a broad spectrum of chemical products.
Used in Pharmaceutical Industry:
Within the pharmaceutical sector, N-(2-aminobenzyl)aniline is employed as a building block in the synthesis of pharmaceuticals, leveraging its chemical properties to contribute to the development of new medicinal compounds.
Used in Dye Production:
In the dye industry, N-(2-aminobenzyl)aniline is harnessed for its capacity to form colorants, playing a crucial role in the production of dyes that have applications across different industries.
Used in Chemical Compounds Synthesis:
N-(2-aminobenzyl)aniline is also used as a component in the synthesis of other organic compounds, highlighting its versatility and importance in the field of chemistry.

Upstream product

• 33331-19-0 N-(2-nitrobenzyl)aniline 
• 62-53-3 aniline 
• 610-14-0 2-nitrobenzyl chloride 
• 17064-77-6 N-(2-nitrobenzylidene)aniline 
• 4424-17-3 2-aminobenzanilide 
• 50-00-0 formaldehyd 
• 56222-13-0 N-(2-Phenylaminomethyl-phenyl)-hydroxylamine 
• 3682-71-1 2-phenyl-2H-indazole 
• 64-17-5 ethanol 
• 141-78-6 ethyl acetate 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 612-23-7 2-nitrobenzyl chloride 
• 622-14-0 N,N'-diphenylmethylenediamine 

Downstream Products

• 28220-33-9 3-phenyl-3,4-dihydro-1H-quinazoline-2-thione 
• 20878-69-7 3-phenyl-3,4-dihydroquinazolin-2(1H)-one 
• 127662-21-9 3-phenyl-1,2,3,4-tetrahydroquinazoline 
• 225-11-6 benz[a]acridine 
• 75063-89-7 3-Phenyl-3,4-dihydro-quinazolin-2-ylamine 
• 60109-71-9 3-phenyl-3,4-dihydro-benzo[d][1,2,3]triazine 

Relevant academic research and scientific papers

Lewis acid solid catalysts for the synthesis of methylenedianiline from aniline and formaldehyde

A catalyst containing Hf4+ and Zn2+ supported on silica has been found to be highly effective for the synthesis of methylenedianiline (MDA), an indispensable precursor in the polyurethane industry. Its performance was further improved when the silica support was replaced by silica-alumina, which resulted in a catalyst that was both active and selective, as indicated by the high MDA yield and high 4,4′–MDA/(2,2′–MDA + 2,4′–MDA) isomer ratio obtained. Furthermore, the catalyst also gave an appreciable oligomeric MDA (OMDA) yield and was noticeably more stable than the zeolites that were used in comparative tests: it could be used in at least five consecutive runs without any significant loss in activity. The combination of Br?nsted and Lewis acidity strongly increases the overall activity and yields a catalyst that represents a remarkably stable and reusable alternative to the commonly studied systems for this reaction.

Integration of Bromine and Cyanogen Bromide Generators for the Continuous-Flow Synthesis of Cyclic Guanidines

A continuous-flow process for the in situ on-demand generation of cyanogen bromide (BrCN) from bromine and potassium cyanide that makes use of membrane-separation technology is described. In order to circumvent the handling, storage, and transportation of elemental bromine, a continuous bromine generator using bromate–bromide synproportionation can optionally be attached upstream. Monitoring and quantification of BrCN generation was enabled through the implementation of in-line FTIR technology. With the Br2 and BrCN generators connected in series, 0.2 mmol BrCN per minute was produced, which corresponds to a 0.8 m solution of BrCN in dichloromethane. The modular Br2/BrCN generator was employed for the synthesis of a diverse set of biologically relevant five- and six-membered cyclic amidines and guanidines. The set-up can either be operated in a fully integrated continuous format or, where reactive crystallization is beneficial, in semi-batch mode.

Transition metal-free α-C(sp3)-H bond functionalization of amines by oxidative cross dehydrogenative coupling reaction: Simple and direct access to C-4-alkylated 3,4-dihydroquinazoline derivatives

A transition metal-free catalytic system has been developed for the cross dehydrogenative coupling of amines with nitroalkanes under mild condition employing potassium iodide/tert-butyl hydrogen peroxide catalytic system. This methodology was further extended for the construction of biologically important N-heterocycles, namely, 3,4-dihydroquinazoline derivatives. This novel strategy provides a simple, efficient, and direct access to 4-alkyl-3,4- dihydroquinazoline derivatives. Copyright

Synthesis of 3h-quinazolin-4-ones and 4h-3,1-benzoxazin-4-ones via benzylic oxidation and oxidative dehydrogenation using potassium iodide-tert-butyl hydroperoxide

A simple and elegant method for benzylic activation was demonstrated employing the potassium iodide/tert-butyl hydrogen peroxide catalytic system. This methodology was further extended for the synthesis of biologically important heterocycles namely, 3H-quinazolin-4-ones and 4H-3,1-benzoxazin-4-ones including mecloqualone and etaqualone which are important quinazolinone-based drugs used for the treatment of insomnia in good yields.

PRODUCTION OF MIXTURES OF METHYLENEDIANILINE AND ITS HIGHER HOMOLOGUES USING CALCINED METAL OXIDE-SILICA CATALYSTS

The present disclosure relates to compositions, systems, and methods of forming an amine (e.g., methylenedianiline (MDA)) using an acid catalyst including, for example, a metal oxide-silica catalyst calcined at temperature(s) of about ≥ 500°C to form a solid acid silica-metal oxide catalyst. A metal oxide of a solid acid silica-metal oxide catalyst may comprise alumina. A process for making a solid acid silica-metal oxide catalyst may comprise calcining an amorphous alumina-silica material at temperature(s) of about ≥ 500°C and/or under an anhydrous and/or inert atmosphere. A rearrangement reaction of the condensation product of aniline and formaldehyde in the presence of a solid acid silica-metal oxide catalyst may yield more MDA and/or more desirable isomer(s) of MDA than reactions performed with a corresponding catalyst calcined at temperature(s) of less than 500°C.

TRINUCLEAR INTERMEDIATES IN ANILINE-FORMALDEHYDE CONDENSATION

The trinuclear intermediate products 4-(4-anilinomethylanilinomethyl)aniline and 4-aniline were isolated and identified by TLC during investigation of the aniline-formaldehyde condensation in the presence of acidic catalysts.The transformation of these compounds and of 4-anilinomethylaniline in methanol and under the conditions of acid aniline-formaldehyde condensation and rearrangement are described.It was established that the fromation of polyamines is possible not only as a result of the initial reaction of the final diamines with formaldehyde but also of the reaction of protonated anilinomethylanilines with aromatic amines present in the reaction mixture.