21650-47-5

Upstream product

• 586-96-9 Nitrosobenzene 
• 540-37-4 p-aminoiodobenzene 
• 3958-47-2 triphenylindium 
• 37790-20-8 (E)-4-(phenyldiazenyl)benzoic acid 
• 636-98-6 p-nitrobenzene iodide 
• 137720-86-6 1-(4-iodophenyl)-2-phenylhydrazine 
• 62-53-3 aniline 
• 131319-20-5 (E)-4-((4-iodophenyl)diazenyl)aniline 
• 6247-00-3 N,N-diallylaniline 
• 20893-72-5 4-iodobenzenediazonium chloride 
• 53547-14-1 4-iodo-cis-azobenzene 
• 60-09-3 4-Aminoazobenzene 

Downstream Products

• 53547-14-1 4-iodo-cis-azobenzene 
• 85572-14-1 (Z)-N-(4-iodo-phenyl)-N'-phenyl-diazene-N-oxide 
• 81710-98-7 (Z)-2-(4-iodophenyl)-1-phenyldiazene 1-oxide 
• 137720-86-6 1-(4-iodophenyl)-2-phenylhydrazine 
• 1070337-91-5 (E)-1-Phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)diazene 

Relevant academic research and scientific papers

Reversibly caged glutamate: A photochromic agonist of ionotropic glutamate receptors

The design, synthesis, and biological evaluation of a photochromic glutamate analogue is described. The molecule functions as a reversibly caged neurotransmitter and can be used to influence neural activity with light. Copyright

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

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

Active ester functionalized azobenzenes as versatile building blocks

Azobenzenes are important molecular switches that can still be difficult to functionalize selectively. A high yielding Pd-catalyzed cross-coupling method under mild conditions for the introduction of NHS esters to azobenzenes and diazocines has been established. Yields were consistently high with very few exceptions. The NHS functionalized azobenzenes react with primary amines quantitatively. These amines are ubiquitous in biological systems and in material science.

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.

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.

Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines: A Practical Chemical Oxidation to Access Azo Compounds

A highly efficient, metal-free, chemical oxidation of hydrazines has been implemented using environmentally friendly TCCA as oxidant. This benign protocol provides straightforward access to a wide range of azo compounds in THF in excellent yield. Altogether, 35 azo compounds were obtained in this way and scale-up preparations were performed. Additionally, a plausible mechanism was also proposed. Step-economical process, mild reaction conditions, operational simplicity, high reaction efficiency, and easy scale-up highlight the practicality of this methodology.

Catalytic Enantio- And Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers

We report the catalytic enantio- and diastereoselective preparation of aminocyclopropanes by the cyclopropanation of terminal and (Z)-internal 2-azadienes with donor/acceptor carbenes derived from α-diazoesters. The resulting cyclopropanes bear quaternary carbon stereogenic centers vicinal to the amino-substituted carbon and are formed as a single diastereomer in up to 99:1 er and 97% yield with 0.5 mol % of Rh2(DOSP)4 and only 1.5 equiv of the diazo reagent. Transformations with internal azadienes afford cyclopropanes with three contiguous stereogenic centers.

Photoactive Boron-Nitrogen-Carbon Hybrids: From Azo-borazines to Polymeric Materials

In this paper, we describe synthetic routes for preparing a novel switchable BNC-based chromophore, composed of a borazine core peripherally functionalized with azobenzene moieties. Capitalizing on the Pd-catalyzed Suzuki cross-coupling reaction between a

Azobenzene-Equipped Covalent Organic Framework: Light-Operated Reservoir

Light-operated materials have gained significant attention for their potential technological importance. To achieve molecular motion within extended networks, stimuli-responsive units require free space. The majority of the so far reported 2D-extended org