63213-03-6

Basic information

• Product Name: Diazene, bis(3-bromophenyl)-, (Z)-
• CAS NO: 63213-03-6
• Molecular Formula: C12H8Br2N2
• Molecular Weight: 340.017
• Mol File: 63213-03-6.mol

Chemical Properties

• CAS DataBase Reference: Diazene, bis(3-bromophenyl)-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, bis(3-bromophenyl)-, (Z)-(63213-03-6)
• EPA Substance Registry System: Diazene, bis(3-bromophenyl)-, (Z)-(63213-03-6)

Safety Data

• Hazardous Substances Data: 63213-03-6(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 585-79-5 m-nitrobromobenzene 
• 23377-24-4 1,2-bis(3-bromophenyl)diazene oxide 
• 55138-19-7 1,2-bis(3-bromophenyl)hydrazine 
• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 23377-24-4 bis-(3-bromo-phenyl)-diazene-N-oxide 
• 591-19-5 m-Bromoaniline 
• 302-01-2 hydrazine 
• 98-95-3 nitrobenzene 
• 99-08-1 1-methyl-3-nitrobenzene 
• 3623-23-2 4-bromonitrosobenzene 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 591-19-5 m-Bromoaniline 
• 55138-19-7 1,2-bis(3-bromophenyl)hydrazine 
• 23377-24-4 1,2-bis(3-bromophenyl)diazene oxide 
• 10286-85-8 N-(3-bromophenyl)benzamide 

Relevant articles and documents

Single crystal MnOOH nanotubes for selective oxidative coupling of anilines to aromatic azo compounds

Catalytic synthesis of aromatic azo compounds by oxidative coupling of anilines using molecular oxygen represents a facile, green and valuable process; however, such an economical process suffers from poor catalytic activity and selectivity. Herein, novel single crystal MnOOH nanotubes with abundant Mn3+sites and high oxygen defects were successfully synthesized. The catalyst exhibited high selectivity for oxidative coupling of anilines, achieving complete transformation into aromatic azo compounds under mild conditions, even at room temperature.

Synthesis of novel 1,2-diarylpyrazolidin-3-one–based compounds and their evaluation as broad spectrum antibacterial agents

There is a continuous need to develop new antibacterial agents with non-traditional mechanisms to combat the nonstop emerging resistance to most of the antibiotics used in clinical settings. We identified novel pyrazolidinone derivatives as antibacterial hits in an in-house library screening and synthesized several derivatives in order to improve the potency and increase the polarity of the discovered hit compounds. The oxime derivative 24 exhibited promising antibacterial activity against E. coli TolC, B. subtilis and S. aureus with MIC values of 4, 10 and 20 μg/mL, respectively. The new lead compound 24 was found to exhibit a weak dual inhibitory activity against both the E. coli MurA and MurB enzymes with IC50 values of 88.1 and 79.5 μM, respectively, which could partially explain its antibacterial effect. A comparison with the previously reported, structurally related pyrazolidinediones suggested that the oxime functionality at position 4 enhanced the activity against MurA and recovered the activity against the MurB enzyme. Compound 24 can serve as a lead for further development of novel and safe antibiotics with potential broad spectrum activity.

Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids

A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.

Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities

Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.

Visible-light-promoted oxidative dehydrogenation of hydrazobenzenes and transfer hydrogenation of azobenzenes

Azo compounds are widely used in the pharmaceutical and chemical industries. Here, we report the use of a non-metal photo-redox catalyst, Eosin Y, to synthesize azo compounds from hydrazine derivatives. The use of visible-light with air as the oxidant makes this process sustainable and practical. Moreover, the visible-light-driven, photo-redox-catalyzed transfer hydrogenation of azobenzenes is compatible with a series of hydrogen donors such as phenyl hydrazine and cyclic amines. Compared with traditional (thermal/transition-metal) methods, our process avoids the issue of over-reduction to aniline, which extends the applicability of photo-redox catalysis and confirms it as a useful tool for synthetic organic chemistry.

Visible-light triggered selective reduction of nitroarenes to azo compounds catalysed by Ag@organic molecular cages

Herein, a new Ag nanoparticle (Ag NP) loaded organic molecular cage is reported. The obtained Ag@1 can act as a highly efficient heterogeneous catalyst for the selective reduction of nitroarenes to azo compounds under visible-light irradiation.

Palladium-catalyzed cyclizative carbonylation of azobenzenes toward 3H-Indazol-3-ones using formic acid as CO source

A palladium-catalyzed cyclizative carbonylation of azobenzenes has been developed to access 1-acyl 2-aryl 3H-indazol-3-ones in moderate to good yields with good functional compatibility. This procedure proceeded with the sequential ortho-C–H carbonylation and cyclization, where formic acid served as the CO source. The practicability of this transformation was further increased by the employment of facilely available azobenzenes derivatives as one-handled starting materials.

Super electron donor-mediated reductive transformation of nitrobenzenes: A novel strategy to synthesize azobenzenes and phenazines

The transformation of nitrobenzenes into azobenzenes by pyridine-derived super electron donor 2 is described. This method provides an efficient synthesis of azobenzenes because of not requiring the use of expensive transition-metals, toxic or flammable reagents, or harsh conditions. Moreover, when using 2-fluoronitrobenzenes as substrates, phenazines were found to be obtained. The process affords a novel synthesis of phenazines.

Single-atom dispersed Co-N-C catalyst: Structure identification and performance for hydrogenative coupling of nitroarenes

Co-N-C catalysts are promising candidates for substituting platinum in electrocatalysis and organic transformations. The heterogeneity of the Co species resulting from high-temperature pyrolysis, however, encumbers the structural identification of active sites. Herein, we report a self-supporting Co-N-C catalyst wherein cobalt is dispersed exclusively as single atoms. By using sub-?ngstr?m-resolution HAADF-STEM in combination with XAFS and DFT calculation, the exact structure of the Co-N-C is identified to be CoN4C8-1-2O2, where the Co center atom is coordinated with four pyridinic N atoms in the graphitic layer, while two oxygen molecules are weakly adsorbed on Co atoms in perpendicular to the Co-N4 plane. This single-atom dispersed Co-N-C catalyst presents excellent performance for the chemoselective hydrogenation of nitroarenes to produce azo compounds under mild reaction conditions.

Affinity modulation of photoresponsive hosts for fullerenes: Light-gated corannulene tweezers

Six azobenzene derivatives bearing polyaromatic fragments have been prepared and their reversible photoisomerization has been assessed. Corannulene-functionalized molecules have demonstrated excellent switchable hosting abilities towards fullerenes in which an interesting range of affinities has been found. The success of this design relies upon the reversible formation and destruction of tweezer-like structures.