1556876-56-2

Upstream product

• 540-37-4 p-aminoiodobenzene 
• 106-49-0 p-toluidine 
• 120567-90-0 4-iodo-4′-methylazobenzene 
• 661-69-8 hexamethyldistannane 

Downstream Products

• 1556876-06-2 4-(4-nitrophenyl)-4′-methylazobenzene 
• 1556876-08-4 4-(4-cyanophenyl-) 4′-methylazobenzene 
• 1556876-10-8 4-(4-acetylphenyl)-4′-methylazobenzene 
• 30821-46-6 4-phenyl-4′-methylazobenzene 
• 1556876-13-1 4-(2-furanyl-5-aldehyde)-4′-methylazobenzene 
• 1556876-16-4 4-(5-methylcarboxylate-2-furanyl)-4′-methylazobenzene 
• 1556876-20-0 4-(3-methoxyphenyl-) 4′-methylazobenzene 
• 1556876-22-2 4-(2,5-methoxyphenyl)-4′-methylazobenzene 
• 1556876-25-5 4-(5-1,3-benzodioxolyl)-4′-methylazobenzene 
• 1556876-27-7 4-(2-thiophene-yl)-4′-methylazobenzene 
• 1556876-30-2 4-(3-thiophene-yl)-4′-methylazobenzene 
• 1556876-31-3 4-(4-N,N-dimethylaminophenyl)-4′-methylazobenzene 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 118719-04-3 2-<4-(4'-methylphenylazo)phenyl>propan-2-ol 

Relevant academic research and scientific papers

High-Yield Lithiation of Azobenzenes by Tin-Lithium Exchange

The lithiation of halogenated azobenzenes by halogen-lithium exchange commonly leads to substantial degradation of the azo group to give hydrazine derivatives besides the desired aryl lithium species. Yields of quenching reactions with electrophiles are therefore low. This work shows that a transmetalation reaction of easily accessible stannylated azobenzenes with methyllithium leads to a near-quantitative lithiation of azobenzenes in para, meta, and ortho positions. To investigate the scope of the reaction, various lithiated azobenzenes were quenched with a variety of electrophiles. Furthermore, mechanistic 119Sn NMR spectroscopic studies on the formation of lithiated azobenzenes are presented. A tin ate complex of the azobenzene was detected and characterized at low temperature.

Tin-functionalized azobenzenes as nucleophiles in stille cross-coupling reactions

The metalation of azobenzene by halogen-metal exchange typically leads to a reduction of the azo group to give hydrazine derivatives as major byproducts, instead of the desired metalated azobenzene species. In cross-coupling reactions, azobenzenes therefore usually serve as electrophiles, which greatly limits the scope of the reaction. To solve this problem, we have developed a mild and fast method to stannylate azobenzenes in high yields. This research shows that these stannylated azobenzenes can be used as nucleophilic components in Stille cross-coupling reactions with aryl bromides. The cross-coupling products were obtained in high yields ranging from 70 to 93%. With this reversal of the nucleophilic and electrophilic components, cross-coupling products are now accessible in which the aromatic rings coupled to the azobenzene bear functional groups that are sensitive to metalation.