7746-36-3

Basic information

• Product Name: 4-Nitro-2-phenylindole
• Synonyms: 4-Nitro-2-phenylindole;(7-Chloro-4-nitro-1H-indol-2-yl)benzene;7-Chloro-4-nitro-2-phenyl-1H-indole;(4-Nitro-1H-indol-2-yl)benzene;4-Nitro-2-phenyl-1H-indole
• CAS NO: 7746-36-3
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 238.2414
• Mol File: 7746-36-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 477.5 °C at 760 mmHg
• Flash Point: 242.6 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 8.08E-09mmHg at 25°C
• Refractive Index: 1.706
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Nitro-2-phenylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-2-phenylindole(7746-36-3)
• EPA Substance Registry System: 4-Nitro-2-phenylindole(7746-36-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 7746-36-3(Hazardous Substances Data)

Usage

General Description

4-Nitro-2-phenylindole is an organic compound with the molecular formula C14H9NO2. It is a nitro-substituted indole derivative that is commonly used in the synthesis of organic compounds and pharmaceuticals. This chemical is known for its yellow to orange crystalline appearance and has a melting point of 179-181 degrees Celsius. 4-Nitro-2-phenylindole is also used as a fluorescent stain for DNA and RNA due to its ability to intercalate with nucleic acid bases. It has potential applications in the field of biochemistry and molecular biology due to its ability to bind to DNA and RNA molecules, making it useful for research and diagnostic purposes.

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 
• 100-52-7 benzaldehyde 
• 1663-61-2 triethoxymethylbenzene 
• 603-83-8 3-nitro-o-tolylamine 

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 articles and documents

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.

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