5486-04-4

Upstream product

• 89641-06-5 2-iodo benzoyl azide 
• 52470-94-7 (2-iodophenyl)diazomethyl ketone 
• 66370-75-0 methyl (2-iodophenyl)acetate 
• 615-43-0 2-iodophenylamine 
• 609-73-4 o-nitroiodobenzene 
• 17082-12-1 trans-azobenzene 
• 18698-96-9 o-iodophenylacetic acid 
• 62300-07-6 o-iodophenylacetyl chloride 

Downstream Products

• 1003285-41-3 2,2'-bis[bis(pentafluorophenyl)boryl]azobenzene 

Relevant academic research and scientific papers

Convergent Paired Electrochemical Synthesis of Azoxy and Azo Compounds: An Insight into the Reaction Mechanism

A convergent paired electrochemical method was developed for the synthesis of azoxy and azo compounds starting from the corresponding nitroarenes. We propose a unique mechanism for electrosynthesis of azoxy and azo compounds. We find that both anodic and cathodic reactions are responsible for the synthesis of these compounds. The synthesis of azoxy and azo derivatives have been successfully performed in an undivided cell, using carbon rod electrodes, by constant current electrolysis at room temperature.

Synthesis, structure, thermal and cis/trans isomerization of 2,2′-(EMe3)2 (E = C, Si, Ge, Sn) Substituted Azobenzenes

The synthesis of a series of 2,2′-bis(trimethyl)tetrel azobenzenes is reported, evaluating the different synthetic approaches that different group 14 element substituents individually require. The synthetic access to the carbon substituted congener is ver

Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide

A new approach for highly regioselective iodination of azobenzenes with alkyl iodide as the iodinating reagent enabled by Rh-catalyzed oxidative C-H activation has been developed. By changing the oxidant, various mono- and di-iodinated azobenzenes were smoothly obtained in moderate to excellent yields, respectively. The preliminary mechanistic study reveals that the reaction process might undergo electrophilic substitution of the directed ortho metalated five-membered rhodacycle compound by an iodine cationic species generated in situ from alkyl iodide and oxidant.

Oxidative dimerization of anilines with heterogeneous sulfonic acid catalysts

We report herein that suitably supported perfluorosulfonic acids can catalyze the oxidative dimerization of anilines using hydrogen peroxide as a clean oxidant. The reaction does not require the use of organic solvents and affords desired azobenzenes and water as products, minimizing the formation of wastes. The metal-free solid catalyst shows remarkable activity and selectivity for the reaction, which occurs under very mild conditions and with broad functional group tolerance.

The palladium and copper contrast: A twist to products of different chemotypes and altered mechanistic pathways

A novel contrast in palladium and copper catalysis is revealed to form products of different chemotypes resulting in a phenazine to azoarene twist through an altered mechanistic pathway (from non-radical C-H activation mode of C-N coupling to radical N-N coupling) during the oxidative self-coupling of anilines catalysed by Pd-Ag and Cu-Ag nanoclusters.

One-pot preparation of azobenzenes from nitrobenzenes by the combination of an indium-catalyzed reductive coupling and a subsequent oxidation

We demonstrated how a reduction step with a reducing system comprised of In(OTf)3 and Et3SiH and a subsequent oxidation that occurred under an ambient (oxygen) atmosphere allowed the highly selective and catalytic conversion of aromatic nitro compounds into symmetrical or unsymmetrical azobenzene derivatives. This catalytic system displayed a tolerance for the functional groups on a benzene ring: an alkyl group, a halogen, an acetyl group, an ester, a nitrile group, an acetyl group, an ester moiety, and a sulfonamide group.

Phenyliodine(III) diacetate (PIDA) mediated synthesis of aromatic azo compounds through oxidative dehydrogenative coupling of anilines: Scope and mechanism

An efficient and environmentally benign method has been developed for the synthesis of symmetrical and unsymmetrical aromatic azo compounds through phenyliodine(III) diacetate (PIDA) mediated oxidative dehydrogenative coupling of anilines in high yields.

Phenyliodine(III) diacetate (PIDA) mediated synthesis of aromatic azo compounds through oxidative dehydrogenative coupling of anilines: Scope and mechanism

An efficient and environmentally benign method has been developed for the synthesis of symmetrical and unsymmetrical aromatic azo compounds through phenyliodine(III) diacetate (PIDA) mediated oxidative dehydrogenative coupling of anilines in high yields.

Switchable selectivity during oxidation of anilines in a ball mill

A solvent-free method for the direct oxidation of anilines to the corresponding azo and azoxy homocoupling products by using a planetary ball mill was developed. Various oxidants and grinding auxiliaries were tested and a variety of substituted anilines were investigated. It was possible to form chemoselectively either azo, azoxy, or the nitro compounds from reaction of aromatic anilines. The selectivity of the solvent-free reaction is switchable by applying a combination of oxidant and grinding auxiliary. Furthermore, a comparison with other methods of energy input (microwave, classical heating, and ultrasound) highlighted the advantages of the ball mill approach and its high energy efficiency. Grinding reactions: Highly efficient oxidative homocoupling of aromatic amines was performed under solvent-free conditions in a planetary ball mill (see scheme). The choice of solid oxidants and grinding auxiliaries allowed selective generation of the oxidized products. Other methods of energy input are compared with respect to reaction time and energy consumption.

Anti-androgenic activity of substituted azo- and azoxy-benzene derivatives.

Substituted phenylazo and phenylazoxy compounds were systematically prepared and their anti-androgenic activity was measured in terms of (1) the growth-inhibiting effect on an androgen-dependent cell line, SC-3, and (2) the binding affinity to nuclear androgen receptor. Generally, azo/azoxy compounds showed cell toxicity, and the growth-inhibiting effects on SC-3 cells correlated with the toxicity. However, some compounds, including 4,4'-dinitroazobenzene (25), 4,4'-dimethoxyazobenzene (33), and 2,2'-dichloroazoxybenzene (47), possessed potent anti-androgenic activity without apparent cell toxicity.