16054-48-1

Upstream product

• 4418-84-2 4-bromoazobenzene 
• 64-19-7 acetic acid 
• 7726-95-6 bromine 
• 20972-43-4 trans-azoxybenzene 
• 6141-96-4 (E)-1-(4-bromophenyl)-2-phenyldiazene 
• 5089-33-8 2-(4-bromophenyl)-1,1,1,3,3,3-hexamethyldisilazane 
• 586-96-9 Nitrosobenzene 
• 16046-28-9 N-Phenyl-N'-tosyloxydiimid-N-oxid 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 16046-28-9 N'-p-Toluolsulfonyloxy-N-phenyl-diimid-N-oxid 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 4418-84-2 4-bromoazobenzene 
• 6141-96-4 (E)-1-(4-bromophenyl)-2-phenyldiazene 
• 3035-94-7 4-((p-bromophenyl)diazenyl)phenol 
• 115976-68-6 2-(4-cyanophenyl)-1-phenyldiazene 1-oxide 
• 59360-38-2 2-(4-bromo-phenylazo)-phenol 
• 59360-37-1 5-bromo-2-phenylazo-phenol 
• 111078-57-0 4-phenyl-ONN-azoxybenzoic acid 
• 16109-68-5 4-bromo-1-phenyl-NNO-azoxybenzene 

Relevant academic research and scientific papers

Trans-4-bromo-ONN-azoxybenzene at 100 K

The crystal structure of the α isomer of trans-4-bromoazoxybenzene [systematic name: trans-1-(bromophenyl)-2-phenyldiazene 2-oxide], C 12H9BrN2O, has been determined by X-ray diffraction. The geometries of the two molecules in the asymmetric unit are slightly different and are within ～0.02 A for bond lengths, ～2° for angles and ～3° for torsion angles. The azoxy bridges in both molecules have the typical geometry observed for trans-azoxybenzenes. The crystal network contains two types of planar molecules arranged in columns. The torsion angles along the Ar-N bonds are only 7 (2)°, on either side of the azoxy group.

Synthesis of Unsymmetrical Azoxyarenes via Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes

A copper-catalyzed oxidative dehydrogenative coupling of nitrosobenzenes with anilines for the synthesis of unsymmetrical azoxybenzenes was developed. This approach uses O2 as the oxidant. The reaction products are diverse unsymmetrical azoxybe

Synthesis of Unsymmetrical Aromatic Azoxy Compounds by Silver-Mediated Oxidative Coupling of Aromatic Amines with Nitrosoarenes

A silver(I) oxide-mediated synthesis of unsymmetrical aromatic azoxy compounds has been successfully achieved, wherein oxidative coupling reactions between aromatic amines and nitrosoarenes take place in ethanol under air. This reaction has very high economic value because silver(I) oxide is the only oxidant required and no other additive is needed. The resulted silver particles can be easily recovered, while the only other byproduct is water. This new procedure is compatible with various functional groups and proceeds under mild reaction conditions.

Synthesis method of asymmetric azoxybenzene compound

The invention relates to a synthesis method of an asymmetric azoxybenzene compound. According to the synthesis method, in an organic solvent, silver oxide is taken as the only promoter to carry out dehydrogenation condensation reactions. According to the

Rh(III)-Catalyzed [4 + 1]-Annulation of Azoxy Compounds with Alkynes: A Regioselective Approach to 2H-Indazoles

A rhodium-catalyzed regioselective C-H activation/cyclization of azoxy compounds with alkynes has been disclosed to construct a variety of 2H-indazoles. A [4 + 1]-cycloaddition rather than a normal [4 + 2] mode is observed in the process of cyclative capture along with an oxygen-atom transfer and a C≡C triple bond cleavage. This protocol features a broad substrate scope, a good functional group tolerance, and an exclusive regioselectivity.

Rh(III)-Catalyzed Regio- and Chemoselective [4 + 1]-Annulation of Azoxy Compounds with Diazoesters for the Synthesis of 2H-Indazoles: Roles of the Azoxy Oxygen Atom

A Rh(III)-catalyzed tandem C-H alkylation/intramolecular decarboxylative cyclization of azoxy compounds with diazoesters for the synthesis of 3-acyl-2H-indazoles is disclosed. The azoxy instead of the azo group enables a distinct approach for cyclative capture, leading to a [4 + 1]-annulation rather than a classic [4 + 2] manner. The azoxy oxygen atom is traceless after annulation, and further removal from the product is not required. This reaction features a complete regioselectivity for unsymmetrical azoxybenzenes and a compatibility of monoaryldiazene oxides.

Towards the synthesis of azoacetylenes

The synthesis of azoacetylenes (=dialkynyldiazenes) 1 and 2 has been investigated. They represent a still elusive class of chromophores with potentially very interesting applications as novel bistable photochemical molecular switches or as antitumor agents (Fig. 1). Our synthetic efforts have led us alongside three different approaches (Scheme 1). In a first route, it was envisioned to generate the azo (=diazene) bond by photolysis of N,N′-dialkynylated 1,3,4-thiadiazolidine-2,5-diones that are themselves challenging targets (Scheme 2). Attempts are described to obtain the latter by alkynylation of the parent heterocycle with substituted alkynyliodonium salts. In a conceptually similar approach, the no-less-challenging dialkynylated 9,10-dihydro-9,10-diazanoanthracene (29) was to be generated by alkynylation of the unsubstituted hydrazine 28 (Scheme 6). In a second route, the generation of the N=N bond from Br-substituted divinylidenehydrazines (ketene-azines) 35 was attempted in a synthetic scheme involving an aza-Wittig reaction between azinobis(phosphorane) 36 and (triisopropylsilyl)ketene 37 (Scheme 7). Finally, a third approach, based on the formation of the central azo bond as the key step, was explored. This route involved the extrapolation of a newly discovered condensation reaction of N,N-disilylated anilines with nitroso compounds (Scheme 11, and Tables 1 and 2) to the transformation of N,N-disilylated ynamine 55 and nitroso-alkyne 54 (Scheme 13).

Preparation, separation and identification of some para-substituted ONN and NNO trans-azoxybenzenes

A series of para-substituted azoxybenzenes was obtained as model compounds for the investigation on the mechanism of Wallach rearrangement. Oxidation of azobenzenes with hydrogen peroxide in acetic acid solution, provided mixtures of α and β isomers. Some

4-Hydroxy-ONN-azoxybenzene

The oxidation of 4-hydroxyazobenzene provided a mixture of two azoxy compounds, which were separated by column chromatography. The isomer with the higher melting point appeared to belong to the α (ONN) series, as determined by X-ray diffraction. The molecule, C12H10N2O2, is almost planar. The benzene rings are twisted by 11.7 (2) (substituted) and 4.1 (1)° (unsubstituted) with respect to the ONN plane. The molecules are connected to one another by strong O-H···O hydrogen bonds forming chains extended along [001], which are bound by much weaker C-H···O hydrogen bonds forming layers in the bc plane.