626-13-1

Usage

Chemical Properties

Sightly viscous liquid

Upstream product

• 108-39-4 3-methyl-phenol 
• 591-17-3 meta-bromotoluene 
• 108-44-1 1-amino-3-methylbenzene 
• 32578-31-7 3-tolyl triflate 
• 17933-03-8 m-tolylboronic acid 
• 108-41-8 1-chloro-3-methylbenzene 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 591-24-2 3-Methylcyclohexanone 
• 1193-18-6 3-methylcyclohexen-2-one 
• 6850-35-7 3-methylcyclohexan-1-amine 
• 625-95-6 3-Iodotoluene 

Downstream Products

• 184104-80-1 (4'-Iodo-biphenyl-4-yl)-di-m-tolyl-amine 
• 143490-35-1 Di-m-tolyl-dithiocarbamic acid methyl ester 
• 117933-21-8 biphenyl-4-yl-di(m-tolyl)-amine 
• 18992-65-9 2,7-dimethyl-9H-carbazole 
• 203710-89-8 N-(4-bromophenyl)-3-methyl-N-(m-tolyl)aniline 

Relevant academic research and scientific papers

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

The present invention relates to a device for emitting light. Provided are a novel mixture capable of improving stability and longevity, an organic electronic element using the same, and an electronic device thereof. (by machine translation)

Amination of Aryl Boronic Acids with Alkylnitrites: A Convenient Complement to Cu-Promoted Reductive Amination

Copper-catalyzed amination of aryl boronic acids with alkylnitrites leading to symmetrical diarylamines with a practical 50-80% yield was elaborated. Two C(sp2)-N bonds are formed in the one-pot process under mild conditions. This new approach to diarylamines is a complement to the Cu-assisted reductive amination of aryl boronic acids avoiding preliminary synthesis of nitrosoarenes. The possible reaction scheme based on quantum chemical calculations was suggested, clarifying key intermediates.

Direct Synthesis of Diphenylamines from Phenols and Ammonium Formate Catalyzed by Palladium

Arylamines are commercially and synthetically useful compounds with a wide variety of applications. Their preparation has been traditionally achieved using metal-catalyzed C?N coupling reactions with aryl halides. In this work, 17 different diarylamines are prepared from phenols by using ammonium formate as the aminating reagent. Phenolic compounds are more desirable feedstocks, owing to their availability from lignin, making them valuable biorenewable alternatives to aryl halides. Ammonium formate is found to be a convenient surrogate for ammonia and a useful aminating reagent for phenols. Diarylamine products are obtained in good to excellent yields while only water and CO2 are generated as byproducts of the transformation.

Iodine-catalyzed synthesis of N, N ′-diaryl-o-phenylenediamines from cyclohexanones and anilines using DMSO and O2 as oxidants

A novel I2-catalyzed cross-dehydrogenative aromatization of cyclohexanones and anilines to synthesize N,N′-diaryl-o-phenylenediamines has been unprecedentedly developed with dimethyl sulfoxide and oxygen employed as mild terminal oxidants. To prove the rationality of the two separate dehydration steps of the proposed mechanism, a resulting I2-catalyzed cross-dehydrogenative aromatization of cyclohexenones and anilines to synthesize diarylamines has also been reported.

Application of a 2-aryl indenylphosphine ligand in the Buchwald-Hartwig cross-coupling reactions of aryl and heteroaryl chlorides under the solvent-free and aqueous conditions

An efficient solvent-free protocol for the Buchwald-Hartwig cross-coupling reaction of aryl and heteroaryl chlorides with primary and secondary amines using the Pd(dba)2/ligand 1 catalytic system has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.

Versatile routes for synthesis of diarylamines through acceptorless dehydrogenative aromatization catalysis over supported gold-palladium bimetallic nanoparticles

Diarylamines are an important class of widely utilized chemicals, and development of diverse procedures for their synthesis is of great importance. Herein, we have successfully developed novel versatile catalytic procedures for the synthesis of diarylamines through acceptorless dehydrogenative aromatization. In the presence of a gold-palladium alloy nanoparticle catalyst (Au-Pd/TiO2), various symmetrically substituted diarylamines could be synthesized starting from cyclohexylamines. The observed catalysis of Au-Pd/TiO2 was heterogeneous in nature and Au-Pd/TiO2 could be reused several times without severe loss of catalytic performance. This transformation needs no oxidants and generates molecular hydrogen (three equivalents with respect to cyclohexylamines) and ammonia as the side products. These features highlight the environmentally benign nature of the present transformation. Furthermore, in the presence of Au-Pd/TiO2, various kinds of structurally diverse unsymmetrically substituted diarylamines could successfully be synthesized starting from various combinations of substrates such as (i) anilines and cyclohexanones, (ii) cyclohexylamines and cyclohexanones, and (iii) nitrobenzenes and cyclohexanols. The role of the catalyst and the reaction pathways were investigated in detail for the transformation of cyclohexylamines. The catalytic performance was strongly influenced by the nature of the catalyst. In the presence of a supported gold nanoparticle catalyst (Au/TiO2), the desired diarylamines were hardly produced. Although a supported palladium nanoparticle catalyst (Pd/TiO2) gave the desired diarylamines, the catalytic activity was inferior to that of Au-Pd/TiO2. Moreover, the activity of Au-Pd/TiO2 was superior to that of a physical mixture of Au/TiO2 and Pd/TiO2. The present Au-Pd/TiO2-catalyzed transformation of cyclohexylamines proceeds through complex pathways comprising amine dehydrogenation, imine disproportionation, and condensation reactions. The amine dehydrogenation and imine disproportionation reactions are effectively promoted by palladium (not by gold), and the intrinsic catalytic performance of palladium is significantly improved by alloying with gold. One possible explanation of the alloying effect is the formation of electron-poor palladium species that can effectively promote the β-H elimination step in the rate-limiting amine dehydrogenation.

Formal arylation of NH3 to produce diphenylamines over supported Pd catalysts

In the presence of supported Pd nanoparticle catalysts, e.g., Pd/Al2O3, various diphenylamines could be synthesized through acceptorless formal arylation using NH3 or its surrogates, e.g., urea, as nitrogen sources and cyclohexanones as arylation sources. The observed catalysis was truly heterogeneous, and the catalyst was reusable with retention of its high catalytic performance.

Selective one-pot synthesis of symmetrical and unsymmetrical di- and triarylamines with a ligandless copper catalytic system

The one-pot synthesis of symmetrical or unsymmetrical di- or triarylamines using aryl iodides or bromides and LiNH2 as ammonia source is reported. This highly selective method is based, for the first time, on a copper-catalyzed system, which does not require the presence of any additional ligand.

Smiles rearrangement for the synthesis of diarylamines

A protocol for the one-pot synthesis of diarylamines via Smiles rearrangement under microwave irradiation has been developed. Various diarylamines were effectively synthesized starting from readily available substituted phenols, arylamines and chloroacetyl chloride in moderate to good yields (58-92%). ARKAT-USA, Inc.

Cathodic reduction of diazonium salts in aprotic medium

Cathodic reduction of diazonium salts in acetonitrile led to the formation of azobenzenes, in good to moderate yields, and diarylamines as minoritary products. The reactions were carried out at the second reduction potential of the diazonium salts, involving aryl anions in the formation of the products.