92594-44-0

Upstream product

• 65578-58-7 di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 62-53-3 aniline 
• 873-74-5 4-Aminobenzonitrile 
• 51003-24-8 4-Phenylazo-benzonitrile 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 67661-51-2 4-(2H-benzo[d][1,2,3]triazol-2-yl)benzonitrile 
• 137720-87-7 4-(2-phenylhydrazinyl)benzonitrile 

Relevant academic research and scientific papers

Design of phase-transition molecular solar thermal energy storage compounds: compact molecules with high energy densities

A series of compact azobenzene derivatives were investigated as phase-transition molecular solar thermal energy storage compounds that exhibit maximum energy storage densities around 300 J g?1. The relative size and polarity of the functional g

Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions

Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.

Reversible Laser-Induced Bending of Pseudorotaxane Crystals

This study investigated the dynamic photoresponse of pseudorotaxane crystals with azobenzene and ferrocenyl groups in the axle component. X-ray crystallography showed pseudorotaxanes with a methylazobenzene group and a dibromophenylene ring in the cyclic component to exhibit twisting of the trans-azobenzene groups at torsion angles of 17° and 38°, respectively. Repeated alternating laser irradiation of the crystals at 360 and 445 nm produced bending of 20-30° in opposite directions, with no evidence of decay. Under 445 nm irradiation, bending took place within 0.3 s. A crystal of nonsubstituted pseudorotaxane showed bending of only 2° under 360 nm irradiation due to multiple π-π interactions between the planar trans-azobenzene groups. The pseudorotaxane crystals have two chromophores, bent rapidly and reversibly on irradiation at rates depending on the molecular structure.

Copper-catalyzed aerobic oxidative dehydrogenative coupling of anilines leading to aromatic azo compounds using dioxygen as an oxidant

In the air tonight: A novel approach to symmetric and unsymmetric aromatic azo compounds from simple anilines catalyzed by inexpensive CuBr has been disclosed. Air (or dioxygen) was used as an oxidant under mild reaction conditions, with H2O as the byproduct, to make this transformation environmentally benign and very easy to handle.

Cu(I) mediated one-pot synthesis of azobenzenes from bis-Boc aryl hydrazines and aryl halides

N,N′-bis-Boc aryl hydrazines underwent Cu(I) catalyzed couplings with aryl halides to provide N,N′-bis-Boc diaryl hydrazines. The resulting N,N′-bis-Boc diaryl hydrazines are readily oxidized to the azobenzenes in the presence of Cu(I) and a base. A prolo