1601-98-5

Basic information

• Product Name: 1,2-Bis(4-bromophenyl)diazene
• Synonyms: 1,2-Bis(4-bromophenyl)diazene;4,4'-Dibromoazobenzene;Bis(4-bromophenyl)diazene;(E)-bis(4-bromophenyl)diazene
• CAS NO: 1601-98-5
• Molecular Formula: C₁₂H₈Br₂N₂
• Molecular Weight: 340.01
• Mol File: 1601-98-5.mol
• Article Data: 147

Chemical Properties

• Melting Point: 204 °C
• Boiling Point: 406.7°C at 760 mmHg
• Flash Point: 199.7°C
• Appearance: /
• Density: 1.67g/cm³
• Vapor Pressure: 1.88E-06mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1,2-Bis(4-bromophenyl)diazene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(4-bromophenyl)diazene(1601-98-5)
• EPA Substance Registry System: 1,2-Bis(4-bromophenyl)diazene(1601-98-5)

Safety Data

• Hazardous Substances Data: 1601-98-5(Hazardous Substances Data)

Usage

General Description

1,2-Bis(4-bromophenyl)diazene is a chemical compound with the molecular formula C12H8Br2N2. It is a diazene derivative, which is a class of compounds containing two nitrogen atoms connected by a double bond. 1,2-Bis(4-bromophenyl)diazene is a pale yellow solid that is insoluble in water and has a melting point of 74-76°C. It is mainly used as a chemical intermediate for the synthesis of various organic compounds. 1,2-Bis(4-bromophenyl)diazene has potential applications in pharmaceuticals, agrochemicals, and materials science due to its versatile reactivity and ability to participate in diverse chemical transformations. Additionally, it is important to handle 1,2-Bis(4-bromophenyl)diazene with caution as it may be hazardous if not used properly.

InChI:InChI=1/C12H8Br2N2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H/b16-15+

Upstream product

• 17333-82-3 4-bromo-benzenediazonium ion 
• 586-78-7 para-nitrophenyl bromide 
• 106-50-3 1,4-phenylenediamine 
• 19717-43-2 4,4'-dibromo-N,N'-diphenylhydrazine 
• 4418-84-2 4-bromoazobenzene 
• 106-40-1 4-bromo-aniline 
• 110-86-1 pyridine 
• 72437-42-4 [(4-bromophenyl)diazenyl](phenyl)methyl hydroperoxide 
• 5194-50-3 (E,Z)-2,4-hexadiene 
• 118622-96-1 N-(4-bromophenylaminothio)phthalimide 
• 2101-88-4 1-azido-4-bromobenzene 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 19717-43-2 4,4'-dibromo-N,N'-diphenylhydrazine 
• 1215-42-5 4,4'-dibromoazoxybenzene 
• 111122-29-3 1,2-Bis-(4-bromo-phenyl)-tetrahydro-pyridazine-3,6-dione 
• 35427-74-8 4,4'-dideuterioazobenzene 
• 106-40-1 4-bromo-aniline 
• 106190-30-1 4,4′-dibromoazobenzene 
• 57574-08-0 p-bromonitrosobenzene dimer 

Relevant articles and documents

Catalytic oxidation of primary aromatic amines with sodium periodate catalyzed by Mn(III)salophen complex supported on polystyrene-bound imidazole

The catalytic activity of Mn(III)salophen complex supported on polystyrene-bound imidazole, [Mn(salophen)Cl-PSI], was studied in the oxidation of primary aromatic amines in acetonitrile/water, using sodium periodate as an oxygen source. Amines were oxidized efficiently to their corresponding azo derivatives in the presence of this catalyst. The heterogeneous catalyst showed high stability and reusability in the oxidation reactions and could be reused several times without loss of its activity. The effect of different solvents was studied in the oxidation of p-toluidine and CH3CN/H2O was chosen as the solvent.

Formal [4+2] cycloaddition of 3-ethoxycyclobutanones with azo compounds

Azobenzenes reacted with 3-ethoxycyclobutanoes to give 2,3-dihydro-pyridazin-4(1H)-ones by using EtAlCl2as a Lewis acid. Thus, ring cleavage of 3-ethoxycyclobutanones took place to form a zwitterionic intermediate by activation with EtAlCl2, and intermolecular formal [4+2] cycloaddition of the zwitterionic intermediate proceeded with azobenzenes to give 2,3-dihydro-pyridazin-4(1H)-ones after elimination of ethanol. Regioselectivity for cycloaddition of unsymmetrical azobenzenes, ring contraction and chemoselective reduction of 2,3-dihydro-pyridazin-4(1H)-ones, and [4+2] cycloaddition to 4-phenyl-1,2,4-triazolin-3,5-dione are also described.

Continuous and green microflow synthesis of azobenzene compounds catalyzed by consecutively prepared tetrahedron CuBr

An environmentally friendly and cross-selective process intensification for the continuous synthesis of symmetric aromatic azo compounds by using self-made cuprous bromide as the catalyst under mild conditions in the microreactor was developed. A novel tetrahedron cuprous bromide catalyst which shows outstanding catalytic activity and satisfactory stability has been synthesized in continuous flow microreactor. The online immobilization of self-made cuprous bromide on the catalyst bed achieved oxidative coupling of aromatic amines (oxygen as oxidant) and high-performance gas–liquid–solid three-phase reaction, which strongly limited the possibility of undesired reaction pathways, improving product selectivity and reducing waste generation. Meanwhile, the yield of azo-coupling reaction was up to 98% under optimized condition. As compared with earlier traditional method (diazotization reaction) for synthesizing azobenzene, the designed micro-flow process displays signi?cant advances in terms of selectivity, waste emissions, sustainability and productivity. The combination of online immobilization of self-made cuprous bromide and precise and safe control through the microreactor provides a green solution for the industrial production of valuable aromatic azo compounds.

Efficient Catalytic Oxidation of Primary Aromatic Amines to Azo Derivatives by Manganese(III) Tetraphenylporphyrin

The oxidation of primary aromatic amines to the corresponding azo derivatives has been observed in catalytic systems containing manganese(III) tetraphenylporphyrin and sodium periodate in the presence of heterocyclic nitrogen bases acting as axial ligands.

Electrosynthesis of Azobenzenes Directly from Nitrobenzenes

The electrochemical reduction strategy of nitrobenzenes is developed. The chemistry occurs under ambient conditions. The protocol uses inert electrodes and the solvent, DMSO, plays a dual role as a reducing agent. Its synthetic value has been demonstrated by the highly efficient synthesis of symmetric, unsymmetric and cyclic azo compounds.

Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst

Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.