7501-57-7

Usage

Uses

Used in Pharmaceutical Research:
(3-methoxy-4-nitro-phenyl)-phenyl-methanone is used as a research compound for its potential pharmacological activities. It is particularly studied for its potential as an anti-inflammatory and anti-cancer agent due to its chemical structure and properties.
Used in Organic Synthesis:
In the field of organic chemistry, (3-methoxy-4-nitro-phenyl)-phenyl-methanone serves as a valuable intermediate in the synthesis of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile building block in the development of new compounds with specific applications.

InChI:InChI=1/C14H11NO4/c1-19-13-9-11(7-8-12(13)15(17)18)14(16)10-5-3-2-4-6-10/h2-9H,1H3

Upstream product

• 654068-47-0 (R)-3-methoxy-4-nitrobenzilic acid 
• 448-19-1 4-fluoro-2-methoxy-1-nitrobenzene 
• 98-87-3 benzylidene dichloride 
• 91-23-6 2-Nitroanisole 
• 143064-49-7 1-(Ethoxy-phenyl-methyl)-1H-benzotriazole 
• 654068-40-3 (2S,5R)-2-tert-butyl-5-(3-methoxy-4-nitrophenyl)-5-phenyl-1,3-dioxolan-4-one 
• 81036-97-7 (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one 

Relevant academic research and scientific papers

α-Chlorobenzylation of Nitroarenes via Vicarious Nucleophilic Substitution with Benzylidene Dichloride: Umpolung of the Friedel-Crafts Reaction

Readily available α,α-dichlorotoluenes enter a vicarious nucleophilic substitution (VNS) reaction with electron-deficient arenes to give α-chlorobenzylated nitrobenzenes, as well as six- and five-membered heterocycles. Oxidation of the initially formed α-chlorobenzylic carbanions instead of protonation results in formation of diaryl ketones, providing a means for overall nucleophilic C-H benzoylation of electron-deficient aromatic rings. Alternatively, benzoylated nitroarenes can be obtained via the reaction of isolated α-chlorodiarylmethanes with sodium azide.

Highly diastereoselective arylation of (S)-mandelic acid enolate: Enantioselective synthesis of substituted (R)-3-hydroxy-3-phenyloxindoles and (R)-benzylic acids and synthesis of nitrobenzophenones

An easy access to substituted (R)-3-hydroxy-3-phenyloxindoles, (R)-benzylic acids, and benzophenones is described. The reaction of the lithium enolate of the (2S,5S)-cis-1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with several o- and p-halonitrobenzenes proceeds readily to give the corresponding arylation products in good yields and diastereoselectivities. The reduction of the nitro group with Zn/HCl/EtOH in the o-nitro arylation products with concomitant intramolecular aminolysis of the dioxolanone moiety leads directly to enantiomerically pure (R)-3-hydroxy-3- phenyloxindoles. On the other hand the basic hydrolysis of the dioxolanone moiety in all the arylation products (ortho and para) leads to enantiomerically pure substituted (R)-benzylic acids. The oxidative decarboxylation of these latter with oxygen as terminal oxidant in the presence of pivalaldehyde and the Co(III)-Me2opba complex as catalyst gives substituted nitrobenzophenones.

Mandelic Acid as Synthetic Equivalent of Benzoyl Carbanion. Synthesis of Nitrobenzophenones

Nitrobenzophenones are prepared from a mandelic acid dioxolanone. The sequence starts with the aromatic nucleophilic substitution of the enolate of the dioxolanone onto p-fluoronitrobenzenes, followed by hydrolysis of the acetal moiety and oxidative decarboxylation of the resulting α-hydroxyacids. The whole sequence involves the use of mandelic acid as synthetic equivalent of the benzoyl carbanion.

Reactions of 1-(benzotriazol-1-yl)-1-phenoxyalkane and (benzotriazol-1- yl)ethoxyphenylmethane anions with nitroarenes: A new approach to alkyl and aryl p-nitroaryl ketones

p-Nitroaryl alkyl ketones and p-nitroaryl aryl ketones are prepared regioselectively by reactions of non-functionalized nitroarenes and benzotriazole stabilized carbanions.