30504-49-5

Usage

Uses

Azobenzene-d10 (CAS# 30504-49-5) is a useful isotopically labeled research compound.

Upstream product

• 18628-43-8 nitrosobenzene-d₅ 
• 4165-61-1 aniline-d5 
• 1076-43-3 benzene-d6 
• 4165-60-0 nitrobenzene-d5 

Downstream Products

• 17049-65-9 2-phenyl-1,2-dihydro-3H-indazol-3-one 
• 1076-43-3 benzene-d6 
• 34346-16-2 phenyl-d5 
• 1133971-49-9 C₆H₂⁽²⁾H₅⁽¹⁸⁾O₂ 
• 1133971-48-8 C₆H₂⁽²⁾H₅O₂ 

Relevant academic research and scientific papers

Rhodium(III)-catalyzed regioselective C–H nitrosation/annulation of unsymmetrical azobenzenes to synthesize benzotriazole N-oxides via a RhIII/RhIII redox-neutral pathway

A Rh(III)-catalyzed regioselective C–H nitrosation/annulation reaction of unsymmetrical azobenzenes with [NO][BF4] has been developed to achieve high-yielding syntheses of benzotriazole N-oxides with excellent functional group tolerance. Computational studies have revealed that this oxidative C–H functionalization reaction involves an interesting redox-neutral Rh(III)/Rh(III) pathway without the change of Rh oxidation state.

Rh(III)-catalyzed [4?+?1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides toward 3-acyl-(2H)-indazoles

A Rh(III)-catalyzed [4 + 1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides was developed to access 2H-indazoles in moderate to excellent yields with good functional group compatibilities. It proceeded with the sequential insertion of the Rh(III) carbene to the C?H bond and cyclization steps, where sulfoxonium ylides served as efficient and stable carbene precursor.

A New Route to 4-Aminodiphenylamine via Nucleophilic Aromatic Substitution for Hydrogen: Reaction of Aniline and Azobenzene

A new example of nucleophilic aromatic substitution for hydrogen is described which encompasses reacting aniline and azobenzene (1) in the presence of base under aerobic conditions to generate 4-(phenylazo)diphenylamine (2) in high yield.Monitoring the time course of the reaction under anaerobic conditions revealed that hydrazobenzene (9) was formed as an intermediate in the reaction in equal molar amounts as 2.However, under aerobic conditions 9 was shown not to persist in the reaction mixture.The kinetic effect of isotopic substitution on this reaction was probed by competition experiments utilizing equal molar mixtures azobenzene-d10 and undeuterated material which gave a kH/kD of 4.6 +/- 0.1.It was concluded from these studies that azobenzene was functioning as both the electrophile and oxidant in this reaction.Catalytic hydrogenation of 2 generates 4-aminodiphenylamine (4-ADPA) (10) and aniline.These reactions form the basis of a novel synthetic route to 4-ADPA which does not utilize halogenated intermediates or reagents and ultimately relies on O2 as the terminal oxidant in the system.

RUTHENIUM-CATALYSED REARRANGEMENTS OF AZOBENZENES IV. REARRANGEMENTS OF DEUTERATED AZOBENZENES TO 1-PHENYLBENZIMIDAZOLE AND N-PHENYL-1,2-PHENYLENEDIAMINE DERIVATIVES

The ruthenium-catalysed reactions of azobenzene-d10 and 4,4'-disubstituted azobenzene-d8 compounds with non-deuterated tri-n-butylamine, n-butanol or 2-propanol give 1-phenylbenzimidazole or N-phenyl-1,2-phenylenediamine derivatives.The distibution of 1H in the aromatic rings of these products and in the recovered azobenzenes indicated that in all cases ortho-metallation of the azobenzene derivative has occured.The significance of those and other observations for the mechanism of these reactions is discussed.