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Usage

Uses

Used in Organic Synthesis:
4-Nitro-2-phenylindole is used as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. Its unique structure and reactivity make it a valuable building block for the development of new molecules with potential applications in medicine and other fields.
Used in Biochemistry and Molecular Biology:
4-Nitro-2-phenylindole is used as a fluorescent stain for DNA and RNA due to its ability to intercalate with nucleic acid bases. This property allows it to bind to DNA and RNA molecules, making it a useful tool for research and diagnostic purposes in the field of biochemistry and molecular biology.
Used in Diagnostic Applications:
In the diagnostic industry, 4-Nitro-2-phenylindole is used as a fluorescent probe for the detection and analysis of nucleic acids. Its ability to bind specifically to DNA and RNA molecules enables the visualization and quantification of these biomolecules in various assays and techniques, contributing to the advancement of molecular diagnostics.
Used in Research Applications:
In the research industry, 4-Nitro-2-phenylindole is used as a research tool for studying the structure, function, and interactions of nucleic acids. Its fluorescent properties and binding affinity to DNA and RNA make it a valuable asset for investigating molecular mechanisms and pathways in biological systems.

InChI:InChI=1/C14H10N2O2/c17-16(18)14-8-4-7-12-11(14)9-13(15-12)10-5-2-1-3-6-10/h1-9,15H

Upstream product

• 133053-83-5 ethyl N-(2-methyl-3-nitrophenyl)-benzimidate 
• 98-86-2 acetophenone 
• 99-09-2 3-nitro-aniline 
• 98751-32-7 (E)-2-(2-phenylethenyl)-1,3-dinitrobenzene 
• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 10403-47-1 2-bromo 5-nitroaniline 
• 663177-71-7 N-(3-nitrophenyl)-N-[(E)-1-phenylethylidene]amine 
• 606-20-2 2,6-dinitrotoluene 
• 1663-61-2 triethoxymethylbenzene 
• 603-83-8 3-nitro-o-tolylamine 
• 100-52-7 benzaldehyde 

Downstream Products

• 142720-23-8 ethyl 2-phenyl-4-nitroindole-3-acetate 
• 150691-71-7 ethyl 2-phenyl-4-aminoindole-3-acetate 
• 142720-22-7 2-Phenyl-1,5-dihydro-3H-pyrrolo[4,3,2-de]quinolin-4-one 

Relevant academic research and scientific papers

Synthesis of 4- and 6-substituted nitroindoles

Enolizable ketones react with m-nitroaniline in the presence of strong base such as t-BuOK to give 4- and 6-substituted nitroindoles. The reaction proceeds via oxidative nucleophilic substitution of hydrogen in m-nitroaniline with enolate anions in positions ortho to the amino group giving anionic σH adducts that are additionally stabilized by intramolecular interaction between the amino and the carbonyl group. Spontaneous oxidation of the σH adducts followed by the Bayer type condensation of the produced ortho-aminonitrobenzyl ketones gives 4- and 6-substituted nitroindoles. The scope of this reaction and its basic mechanistic features are discussed.

Mild Synthesis of Polyfunctional Benzimidazoles and Indoles by the Reduction of Functionalized Nitroarenes with Phenylmagnesium Chloride

Phenylmagnesium chloride has been used for the conversion of selected nitroarenes into nitrenes. Their insertion into a neighboring sp2 C-H bond yielded functionalized heterocycles. A novel and mild synthesis of polyfunctional benzimidazoles and indoles is described.

A novel method of indole ring system construction: One-pot synthesis of 4- and 6-nitroindole derivatives via base promoted reaction between 3- nitroaniline and ketones

Base promoted condensation of ketones RCOCH2R' with 3-nitroaniline results in formation of the corresponding 4- and 6-nitro-2-R-3-R'-indoles. This multistep process apparently includes oxidative nucleophilic substitution of hydrogen in the arom

Synthesis of Indoles via Ring Closure of 2-Alkylnitroaniline Derivatives.

A variety of nitroindoles have been prepared from imidate, amidine, and sec-anilide derivatives of 2-alkyl-3- or 5-nitroanilines by a base-induced cyclization promoted by dialkyl oxalates.It is shown that essentially the same procedure also can be used to synthesize the corresponding nitroindole-3-glyoxylates in one simple operation.The synthetic potential is discussed and a mechanism is proposed.