20473-57-8

Basic information

• Product Name: dimethyl 3,3'-diazene oxide 1,2-diyldibenzoate
• Synonyms: dimethyl 3,3'-diazene oxide 1,2-diyldibenzoate
• CAS NO: 20473-57-8
• Molecular Weight: 314.298
• Mol File: 20473-57-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dimethyl 3,3'-diazene oxide 1,2-diyldibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 3,3'-diazene oxide 1,2-diyldibenzoate(20473-57-8)
• EPA Substance Registry System: dimethyl 3,3'-diazene oxide 1,2-diyldibenzoate(20473-57-8)

Safety Data

• Hazardous Substances Data: 20473-57-8(Hazardous Substances Data)

Upstream product

• 618-95-1 methyl 3-nitrobenzoate 
• 26960-97-4 methyl 3-nitrosobenzoate 
• 99769-19-4 [3-(methoxycarbonyl)phenyl]boronic acid 
• 4518-10-9 Methyl 3-aminobenzoate 
• 74-88-4 methyl iodide 

Relevant articles and documents

Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel-Bound Catalysts

In the search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel-bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described. The conversion within the microfluidic reactor is analyzed and used for optimizing and validating different parameters. The effects of the different functionalities on conversion, yield, and reaction times are analyzed in detail by NMR. The applicability of this reductive dimerization is demonstrated for a wide range of differently substituted nitrosobenzenes. The effects of these different functionalities on the structure of the obtained azoxyarenes are analyzed in detail by NMR and single-crystal X-ray diffraction. Based on these results, the turnover number and the turnover frequency were determined.

Oxidation of anilines with hydrogen peroxide and selenium dioxide as catalyst

A variety of substituted anilines are selectively oxidized to afford high yields of azoxyarenes by using 30% hydrogen peroxide and selenium dioxide as catalyst in methanol at room temperature. The oxidation of 4-alkoxyanilines under the same reaction conditions furnishes the corresponding 4-alkoxy-N-(4-nitrophenyl)anilines in reasonable yields, alongside other oxidation byproducts. The structure of 4-methoxy-N-(4-nitrophenyl)aniline is elucidated by X-ray crystal structure analysis. From these results, some general aspects of the reaction pathways of aniline oxidation are discussed.