30504-49-5

Basic information

• Product Name: AZOBENZENE-D10
• Synonyms: AZOBENZENE-D10
• CAS NO: 30504-49-5
• Molecular Formula: C₁₂H₁₀N₂
• Molecular Weight: 192.28
• Mol File: 30504-49-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: AZOBENZENE-D10(CAS DataBase Reference)
• NIST Chemistry Reference: AZOBENZENE-D10(30504-49-5)
• EPA Substance Registry System: AZOBENZENE-D10(30504-49-5)

Safety Data

• Hazardous Substances Data: 30504-49-5(Hazardous Substances Data)

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 
• 4165-60-0 nitrobenzene-d5 
• 1076-43-3 benzene-d6 

Downstream Products

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

Relevant articles and documents

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.

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.