663177-53-5

Basic information

• Product Name: 1H-Indole,2-ethyl-5-fluoro-3-methyl-6-nitro-(9CI)
• Synonyms: 1H-Indole,2-ethyl-5-fluoro-3-methyl-6-nitro-(9CI)
• CAS NO: 663177-53-5
• Molecular Formula: C11H11FN2O2
• Molecular Weight: 222.2156432
• Product Categories: ETHYL
• Mol File: 663177-53-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole,2-ethyl-5-fluoro-3-methyl-6-nitro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole,2-ethyl-5-fluoro-3-methyl-6-nitro-(9CI)(663177-53-5)
• EPA Substance Registry System: 1H-Indole,2-ethyl-5-fluoro-3-methyl-6-nitro-(9CI)(663177-53-5)

Safety Data

• Hazardous Substances Data: 663177-53-5(Hazardous Substances Data)

Upstream product

• 364-76-1 4-Fluoro-3-nitroaniline 
• 96-22-0 pentan-3-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.