58665-14-8

Upstream product

• 109799-62-4 2-(2,4-dinitrophenyl)acetyl chloride 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 6775-17-3 2,4-dinitro-1-(2-phenylethynyl)acetylene 
• 1226526-89-1 2-(benzothiazole-2-sulfonyl)-2-(2,4-dinitro-phenyl)-1-phenyl-ethanone 
• 1226527-09-8 2-(5-chloro-benzothiazole-2-sulfonyl)-2-(2,4-dinitro-phenyl)-1-phenyl-ethanone 
• 121-14-2 2,4-dinitrotoluene 
• 100-52-7 benzaldehyde 
• 643-43-6 (2,4-dinitro-phenyl)-acetic acid 
• 99-65-0 meta-dinitrobenzene 
• 98-86-2 acetophenone 
• 7647-01-0 hydrogenchloride 
• 584-48-5 2,4-dinitrobromobenzene 
• 98-88-4 benzoyl chloride 

Downstream Products

• 500992-13-2 2-phenyl-1H-indol-6-ylamine 
• 349419-18-7 2-(2,4-dinitro-phenyl)-N-phenyl-acetamide 
• 500992-30-3 6-nitro-2-phenyl-1H-indole 
• 1388183-60-5 1-hydroxy-2-phenyl-6-nitroindole 
• 540750-27-4 (6-nitro-benz[d]isoxazol-3-yl)-phenyl ketone 

Relevant academic research and scientific papers

A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes

2,4-Dinitrotoluene reacts in the presence of catalytic amounts of DBU with aldehydes to form the corresponding alcohols in good yields (usually above 65%). The obtained alcohols can be readily oxidized to 2,4-dinitrobenzyl ketones, which were used for the synthesis of 6-nitroindoles with various substituents in the 2-position. Starting from non-racemic aldehydes, non-racemic 2-substituted 6-nitroindoles were obtained.

Transition-metal-free formal sonogashira coupling and α-carbonyl arylation reactions

Transition-metal-free formal Sonogashira coupling and α-carbonyl arylation reactions have been developed. These transformations are based on the nucleophilic aromatic substitution (SNAr) of β-carbonyl sulfones to electron-deficient aryl fluorides, producing a key intermediate that, depending on the reaction conditions, gives the aromatic alkynes or α-aryl carbonyl compounds. The development of these reactions is presented and, based on investigations under basic and acidic conditions, mechanisms have been proposed. To develop the formal disclosed that expands the reaction concept. The scope of these reactions is demonstrated for the synthesis of Sonogashira and α-carbonyl arylated products from a range of electron-deficient aryl fluorides with a variety of functional groups and aryl-, heteroaryl-, alkyl-, and alkoxy-substituted sulfone nucleophiles. These transition-metal-free reactions complement the metal-catalyzed versions in terms of substitution patterns, simplicity, and reaction conditions.

Study of a reaction between 1,3-dinitrobenzene and acetophenone in presence of hydroxide ion

The kinetics of the reaction between 1,3-dinitrobenzene (m-DNB) and acetophenone in presence of OH- ion has been studied in aqueous ethanol medium with equimolar concentrations of OH- and acetophenone (in the range 10-4 to 10-3 mol dm-3) and an excess of m-DNB (～5 × 10-2 mol dm-3). At such concentrations the reaction has been shown to be of second order (first order with respect to each of OH- and acetophenone). The final product, p-[1-benzoyl-1′-(2,4-dinitrophenyl)methane] has been isolated and characterised. In the reaction medium it forms a purple coloured 1:1 molecular complex with m-DNB and it is the variation of absorbance of this complex with time which has been followed spectrophotometrically during the course of the reaction.

Electrochemical synthesis of nitroaromatic ketones

Nitroaromatic ketones are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Carbanions of various ketones were added to selected nitroarenes in DMF/ketone mixtures leading to formation of the o