632-52-0

Usage

Purification Methods

Crystallise the hydrazine from 1:1 CHCl3/toluene, 1:5 CHCl3/EtOH (m 149o), *C6H6 or *C6H6/pet ether. Store it in a refrigerator, in the dark. [Beilstein 15 H 125, 15 I 29, 15 III 77, 15 IV 59.]

InChI:InChI=1/C24H20N2/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H

Upstream product

• 122-39-4 diphenylamine 
• 147506-92-1 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl 
• 607-00-1 diphenylformamide 
• 119-61-9 benzophenone 
• 591-50-4 iodobenzene 
• 455-13-0 4-Iodobenzotrifluoride 
• 34690-49-8 N,N-(Diphenyl)benzenesulfenamide 
• 67-64-1 acetone 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 78-78-4 methylbutane 
• 2143-67-1 diphenylaminyl radical 
• 38158-67-7 N-propyl-N-phenylaniline 

Downstream Products

• 34839-24-2 N,N'-bis-(4-nitro-phenyl)-N,N'-diphenyl-hydrazine 
• 29325-54-0 N¹,N¹,N²-triphenylbenzene-1,2-diamine 
• 531-91-9 N,N'-diphenyl-p-phenylenediamine 
• 3665-72-3 5,10-diphenyl-5,10-dihydrophenazine 
• 122-39-4 diphenylamine 
• 382165-80-2 N-nitrosodiphenylamine 
• 13327-85-0 Diphenylamino-triphenylmethan 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 92-52-4 biphenyl 
• 2143-67-1 diphenylaminyl radical 
• 20626-85-1 Dimethyl(diphenylamino)phosphin 
• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 857468-42-9 N-(4-chloro-phenyl)-N',N'-diphenyl-p-phenylenediamine 
• 116599-79-2 [1,4]benzoquinone-diphenylhydrazone-phenylimine; hydrochloride 

Relevant academic research and scientific papers

Bismuth Amides Mediate Facile and Highly Selective Pn–Pn Radical-Coupling Reactions (Pn=N, P, As)

The controlled release of well-defined radical species under mild conditions for subsequent use in selective reactions is an important and challenging task in synthetic chemistry. We show here that simple bismuth amide species [Bi(NAr2)3] readily release aminyl radicals [NAr2]. at ambient temperature in solution. These reactions yield the corresponding hydrazines, Ar2N?NAr2, as a result of highly selective N?N coupling. The exploitation of facile homolytic Bi?Pn bond cleavage for Pn?Pn bond formation was extended to higher homologues of the pnictogens (Pn=N–As): homoleptic bismuth amides mediate the highly selective dehydrocoupling of HPnR2 to give R2Pn?PnR2. Analyses by NMR and EPR spectroscopy, single-crystal X-ray diffraction, and DFT calculations reveal low Bi?N homolytic bond-dissociation energies, suggest radical coupling in the coordination sphere of bismuth, and reveal electronic and steric parameters as effective tools to control these reactions.

Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst

We report an efficient method for the oxidative dehydrogenation of hydrazines and diarylamines in aqueous ethanol using Anderson-type polyoxomolybdate-based iron(iii) as a catalyst and hydrogen peroxide as an oxidant. A series of azo compounds and tetraarylhydrazines were obtained in moderate to excellent yields. The reaction conditions and substrate scopes are complementary or superior to those of more established protocols. In addition, the catalyst shows good stability and reusability in water. The preliminary mechanistic studies suggest that a radical process is involved in the reaction.

A Highly Active, Recyclable and Cost-Effective Magnetic Nanoparticles Supported Copper Catalyst for N-arylation Reaction

Abstract: The immobilization of a copper complex by covalent anchoring of 2-hydroxybenzophenone on the surface of amine-functionalized magnetic nanoparticles was reported. The structure and morphology of the catalyst was characterized by different techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron micrograph (TEM), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDS), vibrating sample magnetometer (VSM) and inductively coupled plasma (ICP) spectroscopy. This efficient and cost effective catalyst was applied in the N-arylation reaction and the products were obtained in good to excellent yields in short reaction times. The cost-effective catalyst demonstrated high stability, which could be facilely separated from the reaction mixture by applying an external magnet and recycled at least four times with only a slight decrease in its activity. Graphic Abstract: [Figure not available: see fulltext.]

Method for realizing N-N coupling of secondary arylamine by utilizing electrochemical reaction

The invention relates to the technical field of organic synthesis, and discloses a method for realizing the N-N coupling of secondary arylamine by utilizing electrochemical reaction, i.e., in a deviceprovided with an anode and a cathode, an Nmethylaniline

Iodine-mediated oxidative N-N coupling of secondary amines to hydrazines

An I2-mediated N-N coupling reaction has been established for oxidative dimerization of N-aryl aminopyridines to a variety of novel hydrazine derivatives under mild conditions. This synthetic method does not require use of transition metals and

Transition-Metal-Free Dehydrogenative N–N Coupling of Secondary Amines with KI/KIO4

A transition-metal-free method for the dehydrogenative N–N coupling of secondary amines has been accomplished. This oxidative KI/KIO4 protocol is mild and operationally simple. A diverse range of diphenylamines, carbazoles, and N-alkylanilines readily undergo N–N homo-coupling effectively. Notably, the N–N cross-coupling of two different arylamines is also demonstrated, which provides a straightforward approach to the complex N–N structures.

Cu-Catalyzed Aerobic Oxidative N-N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

A Cu-catalyzed method has been identified for aerobic oxidative dimerization of carbazoles and diarylamines to the corresponding N-N coupled bicarbazoles and tetraarylhydrazines. The reactions proceed under mild conditions (1 atm O2, 60-80 °C)

Reduction of nitroarenes, azoarenes and hydrazine derivatives by an organic super electron donor

Reduction of nitrobenzene by excess organic electron donor, 12, affords diphenylhydrazine in a reaction where azobenzene oxide and azobenzene are likely intermediates. No cleavage of the N-N σ-bond is seen under photoactivation conditions, whereas traces are seen under thermal activation. Hydrazone derivatives were prepared to explore the cleavage of N-N σ-bonds; the results show that a low-lying LUMO assists the transition state for accepting an electron, and the stabilisation that the potential fragments from N-N bond cleavage afford to the fragments is important in determining whether cleavage is observed.

Cu(I) catalyzed dehydrogenative homo coupling of aromatic amines under simple and mild reaction conditions

An efficient protocol for the synthesis of a variety of azobenzenes and hydrazines from aromatic amines under mild reaction conditions is developed using Cu(I) catalyst. The copper cataylst used in this study comprises of CuBr, DMAP and AIBN. The plausible proposed mechanism for this dehydrogenative homo coupling of aromatic amines is depicted.

Facile Cu(I)-catalyzed oxidative coupling of anilines to azo compounds and hydrazines with diaziridinone under mild conditions

A mild and highly efficient Cu(I)-catalyzed oxidative coupling of anilines is described. Various primary and secondary anilines can be efficiently coupled under mild conditions to the corresponding azo compounds and hydrazines in high yields. This method provides a direct and practical access to these compounds and is also amenable to gram scale with no special precautions to exclude air or moisture.