2369-21-3

Upstream product

• 1493-27-2 ortho-nitrofluorobenzene 
• 348-54-9 2-Fluoroaniline 

Downstream Products

• 90493-82-6 N-(2-Fluorophenyl)benzohydroxamic acid 
• 59478-03-4 3,3-dimethyl-1-(o-fluorophenyl)triazene-1-oxide 
• 858515-78-3 methyl 7-fluoro-1H-indole-3-carboxylate 
• 1403889-71-3 S-5-(acetoxy(2-fluorophenyl)amino)-5-oxo-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-yl O-ethyl carbonodithioate 
• 1403889-70-2 S-5-(acetoxy(2-fluorophenyl)amino)-5-oxo-1-(2-oxocyclohexyl)pentan-2-yl O-ethyl carbonodithioate 
• 1403889-62-2 S-2-(acetoxy(2-fluorophenyl)amino)-2-oxoethyl O-ethyl carbonodithioate 
• 1403889-51-9 C₈H₇ClFNO₂ 
• 90493-88-2 2'-Chloro-6'-fluorobenzanilide 
• 363-51-9 2-chloro-6-fluoroaniline 

Relevant academic research and scientific papers

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of: Para-amino-arylfluorosulfates

The construction of para-amino-arylfluorosulfates was achieved through installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds by the reaction of N-arylhydroxylamine with sulfuryl fluoride (SO2Fs

Hydroxamic Acids as Chemoselective (ortho-Amino)arylation Reagents via Sigmatropic Rearrangement

The use of readily available hydroxamic acids as reagents for the chemoselective (ortho-amino)arylation of amides is described. This reaction proceeds under metal-free, mild conditions, displays a very broad scope, and constitutes a direct approach for the metal-free attachment of aniline residues to carbonyl derivatives.

An unusual synthesis of N-unsubstituted benzazepinones

A short route to novel bicyclic N-unprotected benzazepinones is described starting from N-acetoxyanilides involving radical addition and cyclization with concomitant homolytic rupture of the N-O bond.

Effect of substituents on the rate of oxidation of anilines with peroxomonosulfate monoanion (HOOSO3-) in aqueous acetonitrile: A mechanistic study

Mechanistic studies on the oxidation of 18 meta-, para-, and ortho-substituted anilines (Ans) by HOOSO3- in aqueous acetonitrile medium have been performed. The reaction can be characterized by the experimental rate equation, -d[HSO5-]/dt = k[An][HSO5-] The addition of p-toluenesulfonic acid (TsOH) retards the reaction. The increase in the reactivity of anilines as the medium is made more aqueous is interpreted. The reaction is enhanced by electron-donating groups on the amine in the series consistent with the rate-limiting nucleophilic attack of the amine on the persulfate oxygen. The proposed mechanism involves the conversion of phenylhydroxylamine to nitrosobenzene in a fast step. The ESR study reveals the absence of free radicals in the reaction. Various attempts have been made to analyze the experimental rate constants in terms of LFER plots. Improved correlations are obtained with σ- values and the σ- form of the Yukawa-Tsuno equation.

Novel Reactions: Part I - Facile Synthesis of Substituted ortho-Chloranilines from Nitrobenzene Derivatives

N-Substituted benzo and acetohydroxamic acids (5), prepared from N-arylhydroxylamines and benzoyl or acetyl chloride, react readily with thionyl chloride at low temperature to give ortho-chloroanilide derivatives (6) in good yield.The latter (6) on hydrolysis give ortho-chloroanilines (10).Since the N-arylhydroxylamines are obtained from nitroarenes by partial reduction, the overall reaction amounts to the preparation of 10 from nitroarenes.

N'Cyclopropyl-N-(fluorophenyl)-N-hydroxyureas

N'-cyclopropyl-N-(2-fluorophenyl)-2-hydroxyurea and its 2,5-difluorophenyl congener, useful as selective herbicides.