7466-42-4

Usage

InChI:InChI=1/C18H14N2/c1-3-7-15(8-4-1)16-11-13-18(14-12-16)20-19-17-9-5-2-6-10-17/h1-14H/b20-19+

Upstream product

• 100-34-5 benzene diazonium chloride 
• 619-97-6 benzenediazonium nitrate 
• 1227476-15-4 Azobenzene 
• 71-43-2 benzene 
• 495-48-7 azoxybenzene 
• 92-67-1 4-phenylalanine 
• 586-96-9 Nitrosobenzene 
• 62-53-3 aniline 
• 99-65-0 meta-dinitrobenzene 
• 23265-32-9 1-(methylsulfonyl)-2-(phenyl)diazene 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 17082-12-1 trans-azobenzene 
• 72358-76-0 phenylhydrazine acetate 

Downstream Products

• 92-67-1 4-phenylalanine 
• 62-53-3 aniline 
• 5326-53-4 1,2-di([1,1'-biphenyl]-4-yl)diazene 
• 34161-43-8 1-phenyl-2-([1,1'-biphenyl]-4-yl)hydrazine 

Relevant academic research and scientific papers

Cu(I) mediated one-pot synthesis of azobenzenes from bis-Boc aryl hydrazines and aryl halides

N,N′-bis-Boc aryl hydrazines underwent Cu(I) catalyzed couplings with aryl halides to provide N,N′-bis-Boc diaryl hydrazines. The resulting N,N′-bis-Boc diaryl hydrazines are readily oxidized to the azobenzenes in the presence of Cu(I) and a base. A prolo

Polar Effects in Reactions of Carbon-Centered Radicals with Diazonium Salts: Free-Radical Diazocoupling

Carbon-centered radicals react with diazonium salts by addition, leading under reductive conditions to azo derivatives (free-radical diazocoupling), or by electron-transfer in chain processes.The reaction is highly sensitive to polar effects and it has been investigated by three different processes: (i) alkyl radicals, generated from alkyl iodides, H2O2, Fe(II) salt, and DMSO, have been utilized to develop a new general synthesis of alkylarylazo compounds; (ii) the reaction of aryl radicals with diazonium salts in the presence of Ti(III) or Fe(II) salts has been investigated, also in relation to the fact that the reaction products (azoarenes and biaryls) are often detected as side products in classical organic reactions of diazonium salts, catalyzed by Cu(I) salts, such as the Sandmeyer, Meerwein, and Pschorr reactions; (iii) adducts from addition of aryl radicals to vinyl acetate or vinyl ether react with diazonium salts either by diazocoupling reaction or by electron-transfer; a general synthesis of arylazo compounds has been developed.

Acid-Catalyzed Reactions of N-Arylhydroxylamines and Related Compounds with Benzene. Iminium-Benzenium Ions

N-Arylhydroxylamines react with benzene in the presence of trifluoroacetic acid (TFA) at room temperature to give diphenylamines.When TFA was replaced by a strong acid, trifluoromethanesulfonic acid (TFSA), the major products were aminobiphenyls.The nature of the reaction was explored by reactions of 4-substituted phenylhydroxylamines and dialkylaniline N-oxides with benzene.Thus, it was demonstrated that the reactive intermediates are onium-benzenium dications which are trapped by benzene to give aminobiphenyls by a mechanism similar to the Friedel-Krafts alkylation.Further evidence for the proposed reaction mechanism was the observation that nitrosobenzene and azoxybenzene reacted with benzene to give analogous products in the presence of the stronger acid.