36966-93-5

Basic information

• Product Name: 4-bromo-benzene-standarddiazohydroxide-⁽¹⁾
• CAS NO: 36966-93-5
• Molecular Weight: 201.023
• Mol File: 36966-93-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-bromo-benzene-standarddiazohydroxide-⁽¹⁾(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-benzene-standarddiazohydroxide-⁽¹⁾(36966-93-5)
• EPA Substance Registry System: 4-bromo-benzene-standarddiazohydroxide-⁽¹⁾(36966-93-5)

Safety Data

• Hazardous Substances Data: 36966-93-5(Hazardous Substances Data)

Upstream product

• 17333-82-3 4-bromo-benzenediazonium ion 
• 103-88-8 4-bromoacetanilide 
• 35920-23-1 acetic acid-(4-bromo-N-nitroso-anilide) 

Relevant articles and documents

Formation of diazohydroxides ArN2OH in aqueous acid solution: Polarographic determination of the equilibrium constant KR for the reaction of 4-substituted arenediazonium ions with H2O

In aqueous acid (pH 2+ decompose spontaneously through the rate-limiting formation of the extremely unstable aryl cation that reacts with any nucleophile present in its solvation shell (D N-‰+-‰AN mechanism). However, in weak acidic and alkaline solutions, ArN2+ react with H2O and OH- at the terminal nitrogen to give azo adducts of the type ArN2OH that are in equilibrium with the parent ArN2 +. The diazohydroxide, in this case an acid, is in equilibrium with its conjugate base, and diazoate ArN2O-. The equilibrium constant for reaction with OH- has been determined for a limited number of ArN2+ from kinetic measurements but not with H2O (KR). Here, we have exploited the electrochemical properties of ArN2+ to determine, for the first time, the equilibrium constants KR of formation of 4-substituted X-ArN 2OH (Xi￡H, Me, MeO, Br, and NO2), which can decompose in several ways including Z-E isomerization or further reaction with OH- to give diazoate ArN2O-. The technique applied was differential pulse polarography, which is very selective and sensitive. The determined pKR values are 5-6, and they are somewhat higher than those obtained for the reaction of ArN2+ with alcohols ROH (pKDE-‰=-‰3-5) under similar acidic conditions. The KR values are not very sensitive to changes in the nature of the substituent in the aromatic ring and a linear Hammett plot with a slope of ρ-‰=-‰0.58 was obtained.