98217-68-6

Upstream product

• 86885-33-8 syn-4-Trifluoromethylazobenzene 
• 455-14-1 4-trifluoromethylphenylamine 
• 586-96-9 Nitrosobenzene 
• 60-09-3 4-Aminoazobenzene 
• 77152-08-0 trifluoromethylcopper(I) 
• 98-95-3 nitrobenzene 
• 1815-14-1 1-phenyl-2-(4-(trifluoromethyl)phenyl)diazene 
• 1815-08-3 1-phenyl-2-(4-(trifluoromethyl)phenyl)hydrazine 

Downstream Products

• 501917-68-6 2-(4-(trifluoromethyl)phenyl)–2H-indazole 
• 1815-08-3 1-phenyl-2-(4-(trifluoromethyl)phenyl)hydrazine 
• 455-14-1 4-trifluoromethylphenylamine 
• 62-53-3 aniline 

Relevant academic research and scientific papers

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.

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.

Electrochemical dehydrogenation of hydrazines to azo compounds

A strategy for the electrochemical dehydrogenation of hydrazine compounds is disclosed under ambient conditions. This protocol proceeded smoothly in ethanol by employing electrons as clean oxidants. Its synthetic value is well demonstrated by the highly efficient synthesis of symmetric and unsymmetric azo compounds. It is an environmentally friendly transformation and the present protocol was effective on a large scale.

Dehydrogenation of the NH?NH Bond Triggered by Potassium tert-Butoxide in Liquid Ammonia

A novel strategy for the dehydrogenation of the NH?NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH3) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one-pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.

Conversion of aromatic amino into trifluoromethyl groups through a Sandmeyer-type transformation

A novel strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions. Georg Thieme Verlag Stuttgart. New York.

Trifluoromethylation of arenediazonium salts with fluoroform-derived CuCF3 in aqueous media

A new protocol has been developed for trifluoromethylation of arenediazonium salts with moisture-sensitive CuCF3 (from fluoroform) in aqueous media. The reaction is governed by a radical mechanism, tolerates a broad variety of functional groups, and is applicable to the synthesis of complex, polyfunctionalized molecules. This journal is the Partner Organisations 2014.

Silver-mediated trifluoromethylation of aryldiazonium salts: Conversion of amino group into trifluoromethyl group

A novel strategy for aromatic trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is performed under mild conditions.

Copper-promoted sandmeyer trifluoromethylation reaction

A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.

Liquid Crystalline Solvents as Mechanistic Probes. 11. The Syn -> Anti Thermal Isomerization Mechanism of Some Low-"Bipolarity" Azobenzenes

The effects of solvent order on the syn -> anti isomerization rates of 15 azobenzenes have been investigated.The activation parameters determined in a cholesteric phase consisting of a 35/65 (w/w) mixture of cholesteryl chloride/cholesteryl nonanoate and in several other solvents are more consistent with an isomerization mechanism which proceeds via inversion (in plane) rather than rotation (out of plane).A correction of our previously reported data is given.The anomalous behavior of the isomerization mechanism of di-ortho-methylated azobenzenes is demonstrated by means of isokinetic plots.