64554-26-3

Usage

Type of compound

Radical cation form of o-Phenylenediamine

Usage

Commonly used in the synthesis of various organic compounds

Reactivity

Highly reactive species

Role in chemistry

Used as a radical cation source in organic chemistry

Studies

Investigated for potential applications in organic synthesis

Reactions

Known for its ability to participate in a variety of chemical reactions

Hazard

Can be hazardous if not properly managed

Oxidation

Known for its ability to undergo oxidation reactions

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 584-48-5 2,4-dinitrobromobenzene 
• 618-86-0 1-chloro-3,5-dinitrobenzene 
• 108-36-1 1,3-dibromobenzene 
• 535-87-5 3.5-diaminobenzoic acid 
• 603-12-3 2,6-dinitrobenzoic acid 
• 51686-79-4 2,4,6-tribromo-1,3-dinitrobenzene 
• 3027-36-9 isophthaloyl diazide 
• 98-95-3 nitrobenzene 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 99-09-2 3-nitro-aniline 
• 610-30-0 2,4-dinitrobenzoic acid 
• 108-46-3 recorcinol 

Downstream Products

• 6265-21-0 3-[(2-hydroxy-ethyl)amino]aniline 
• 90434-85-8 2-(3-amino-anilino)-ethanethiol 
• 31992-43-5 1-(3-aminophenyl)pyrrolidin-2-one 
• 79461-25-9 N,N'-m-phenylenedisuccinamic acid 
• 1138-69-8 N-(3-amino-phenyl)-succinamic acid 
• 4288-20-4 N,N'-bis-(4-methyl-thiazol-2-yl)-m-phenylenediamine 
• 25227-71-8 N,N'-m-phenylene-bis-propionamide 
• 36210-57-8 1,5-diamino-2,4-dibromobenzene 
• 15667-18-2 N,N'-bis(benzylidene)-m-phenylenediaine 
• 27919-85-3 N¹,N¹,N³,N³-tetrabenzylbenzene-1,3-diamine 
• 64287-26-9 N,N,N',N'-Tetraethyl-m-phenylenediamine 

Relevant academic research and scientific papers

FeS-NH4Cl-CH3OH-H2O: An efficient and inexpensive system for reduction of nitroarenes to anilines

Nitroarenes are reduced to corresponding anilines with FeS-NH4Cl-CH3OH-H2O system in good yields.

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).

Au/Ni/Ni(OH)2/C Nanocatalyst with High Catalytic Activity and Selectivity for m-dinitrobenzene Hydrogenation

The Au/Ni/Ni(OH)2/C bimetallic nanocatalysts with different Au loadings (Au/Ni/Ni(OH)2/C-1: 0.05 wt%Au; Au/Ni/Ni(OH)2/C-2: 0.46 wt%Au; Au/Ni/Ni(OH)2/C-3: 2.60 wt%Au) were prepared at room temperature. The characterization results proved the nanostructure of Au islands supported on the Ni/Ni(OH)2 nanoparticles (NPs) and synergy effect of Au-, Ni- and Ni(OH)2-related species in Au/Ni/Ni(OH)2/C. These are the main reasons why their catalytic performance and selectivity to m-nitroaniline in m-dinitrobenzene hydrogenation were much higher than those of monometallic catalysts (Au/C and Ni/Ni(OH)2/C). Because Au/Ni/Ni(OH)2/C-2 was with high dispersion of Au, Au(0)/Aun+ ratio≈1:1 on the surface, novel nanostructure, moderate capacity of activating and dissociating hydrogen, and synergistic effect, it had much better catalytic activity (conversion of m-dinitrobenzene-100%) and higher selectivity to m-nitroaniline (95.0%) in m-dinitrobenzene hydrogenation reaction compared to other two supported bimetallic catalysts (Au/Ni/Ni(OH)2/C-1 and Au/Ni/Ni(OH)2/C-3). Au/Ni/Ni(OH)2/C-2 also exhibited high stability. Graphic abstract: [Figure not available: see fulltext.]

Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines

Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.

Rhodium nanoparticles supported on 2-(aminomethyl)phenols-modified Fe3O4 spheres as a magnetically recoverable catalyst for reduction of nitroarenes and the degradation of dyes in water

A magnetic nanostructured catalyst (Fe3O4@SiO2-Amp-Rh) modified with 2-(aminomethyl)phenols (Amp) was designed and prepared, which is used to catalyze the reduction of aromatic nitro compounds into corresponding amines and the degradation of dyes. The 2-aminomethylphenol motif plays a vital role in the immobilization of rhodium nanoparticles to offer extraordinary stability, which has been characterized by using various techniques, including transmission electron microscopy (TEM), thermal gravimetric analyzer (TGA), X-Ray Diffraction (XRD), and X-ray photoelectron spectroscopy (XPS). A variety of nitroaromatic derivatives have been reduced to the corresponding anilines in water with up to yields of 99% within 1?h at room temperature. In addition, the catalyst system is effective in catalyzing the reduction of toxic pollutant 4-nitrophenol and the degradation of MO, MB and RhB dyes. Importantly, this catalyst Fe3O4@SiO2-Amp-Rh can be easily recovered by an external magnetic field because of the presence of magnetic core of Fe3O4, and the activity of Fe3O4@SiO2-Amp-Rh does not decrease significantly after 7 times’ recycling, which indicates that the catalyst performed high reactivity as well as stability. Graphical abstract: [Figure not available: see fulltext.]

Magnetically‐recoverable Schiff base complex of Pd(II) immobilized on Fe3O4@SiO2 nanoparticles: an efficient catalyst for the reduction of aromatic nitro compounds to aniline derivatives

Fe3O4@SiO2/Schiff base/Pd(II) is reported as a magnetically recoverable heterogeneous catalyst for the chemoselective reduction of aromatic nitro compounds to the corresponding amines through catalytic transfer hydrogenation (CTH). In this regard, a small amount of the nanocatalyst (0.52?mol% Pd) and hydrazine hydrate, showing safe characteristics and perfect ability as the hydrogen donor, were added to the nitro substrates. The experiments described the successful reduction of aromatic nitro compounds with good to excellent yields and short reaction times. The catalyst, due to its magnetic property, could be simply separated from the reaction mixture by a permanent magnet and reused in seven consecutive reactions without considerable loss in its activity. Moreover, the leaching of Pd was only 3.6% after the seventh run. Thus, the most striking feature of this method is to use a small amount of the magnetic nanocatalyst along with a cheap and safe hydrogen source to produce the important amine substances selectively, which makes the method economical, cheap, environmentally friendly, and simple. Graphic abstract: [Figure not available: see fulltext.]

Copper nanoparticles (CuNPs) catalyzed chemoselective reduction of nitroarenes in aqueous medium

Abstract: A procedure for practical synthesis of CuNPs from CuSO4·5H2O is established, under appropriate reaction conditions, using rice (Oryza sativa) as an economic source of reducing as well as a stabilizing agent. Optical and microscopic techniques are employed for the characterization of the synthesized CuNPs and the sizes of the particles were found to be in the range of 8 ± 2 nm. The nanoparticles are used as a catalyst for chemoselective reduction of aromatic nitro compounds to corresponding amines under ambient conditions and water as a reaction medium. Graphic abstract: CuNPs are synthesized using hydrolysed rice and used as catalyst for chemoselective reduction of nitroarenes to their corresponding amines in water. [Figure not available: see fulltext.]

Rhodium-terpyridine Catalyzed Transfer Hydrogenation of Aromatic Nitro Compounds in Water

A rhodium terpyridine complex catalyzed transfer hydrogenation of nitroarenes to anilines with i-PrOH as hydrogen source and water as solvent has been developed. The catalytic system can work at a substrate/catalyst (S/C) ratio of 2000, with a turnover frequency (TOF) up to 3360 h?1, which represents one of the most active catalytic transfer hydrogenation systems for nitroarene reduction. The catalytic system is operationally simple and the protocol could be scaled up to 20 gram scale. The water-soluble catalyst bearing a carboxyl group could be recycled 15 times without significant loss of activity.

Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water

Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].

Crosslinked polymer encapsulated palladium nanoparticles for catalytic reduction and Suzuki reactions in aqueous medium

Acrylamide and N-isopropylacrylamide were copolymerized in the presence of a N,N-methylenebisacrylamide crosslinker to obtain poly(N-isopropylacrylamide-co-acrylamide) [P(NA)] polymer colloidal particles. Pd nano crystals with diameter of 4–8 nm were loaded into the [P(NA)] microgels by reduction of [PdCl4]-2 within dispersion of polymer microgels. The Pd NPs-loaded hybrid microgels were analysed by TEM, STEM, EDX and XRD. The catalytic ability of the Pd-[P(NA)] system was investigated towards reductive transformation of nitroarenes into corresponding aryl amines and Suzuki coupling transformation in a green solvent, H2O. The progress of catalytic reaction was examined by thin layer chromatography (TLC). Different reactants were effectively converted into their corresponding products with great to fabulous yields (extending from 75 to 97%) under gentle reaction conditions. The Pd-[P(NA)] catalyst is stable for long time and can be utilized numerous times without any notable loss in its catalytic action.