3260-61-5

Basic information

• Product Name: 3H-indol-3-one
• Synonyms: 1,2-Dihydro-3H-indol-3-one;2,3-Dihydro-1H-indole-3-one;3-Oxoindoline;Indol-3(2H)-one;Indoline-3-one;Pseudoindoxyl;1,2-Didydroindol-3-one;2,3-dihydro-1H-indol-3-one
• CAS NO: 3260-61-5
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.05
• Mol File: 3260-61-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 282.463 °C at 760 mmHg
• Flash Point: 139.886 °C
• Appearance: /
• Density: 1.198 g/cm³
• Vapor Pressure: 0.00335mmHg at 25°C
• Refractive Index: 1.586
• PKA: 1.46±0.20(Predicted)
• CAS DataBase Reference: 3H-indol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-indol-3-one(3260-61-5)
• EPA Substance Registry System: 3H-indol-3-one(3260-61-5)

Safety Data

• Hazardous Substances Data: 3260-61-5(Hazardous Substances Data)

Usage

General Description

3H-indol-3-one, also known as indoxyl, is a heterocyclic compound with a bicyclic structure that consists of a benzene ring fused to a five-membered nitrogen-containing ring. It is a derivative of indole and is widely used in the pharmaceutical and cosmetic industries. 3H-indol-3-one has a variety of biological and pharmacological activities, including antimicrobial, antioxidant, and anti-inflammatory properties. It is also a precursor in the synthesis of indigo dye, which has been used for centuries in various cultures for textile dyeing. Additionally, 3H-indol-3-one has been studied for its potential applications in the treatment of various diseases, including cancer and neurodegenerative disorders.

InChI:InChI=1/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-4,9H,5H2

Upstream product

• 6411-55-8 2-phenylimino-indolin-3-one 
• 51972-83-9 2-anilino-indolin-3-one 
• 480-93-3 indoxyl 
• 6245-93-8 3-hydroxy-1H-indole-2-carboxylic acid 
• 4127-53-1 3-methylbenzo[c]isoxazole 
• 120-72-9 indole 
• 103-01-5 N-Phenylglycine 
• 16712-55-3 3-methoxyindole 
• 150-61-8 N,N'-diphenylethylenediamine 
• 872276-42-1 1-(2-amino-phenyl)-2-hydroxy-ethanone 
• 16714-26-4 1-(2-azido-phenyl)-ethanone 

Downstream Products

• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 3265-35-8 indoline-2,3-dione-2-oxime 
• 114947-35-2 2-(xanthen-9-yliden-ethylidene)-indolin-3-one 
• 480-93-3 indoxyl 
• 120-72-9 indole 
• 243-58-3 quindoline 
• 1233241-53-6 2,2-dimethyl-5-(3-oxo-2,3-dihydro-1H-indol-1-ylmethylene)-1,3-dioxane-4,6-dione 
• 133593-42-7 2-[(dimethylamino)methylene]-1,2-dihydro-3H-indol-3-one 
• 39830-75-6 2-benzylideneindolin-3-one 
• 479-41-4 indirubin 
• 13220-57-0 tryptanthrine 

Relevant articles and documents

Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene

Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azido[1]benzothiophene at 300 °C provides 3-methyl [1]benzothieno[3,2-c]isoxazole (72%). At higher temperatures, the heteroindoxyl 1,2-dihydro[1]benzo-thieno[3,2-b]pyrrol-3-one was obtained in low yield (ca. 10%). The heteroindoxyl exists as a mixture of keto and enol forms in DMSO solution. Because of the easy oxidative dimerisation of these products to indigotin (and its heteroanalogues), such reactions are excellent examples of the synthetic advantages of FVP with the monomeric products conveniently generated under vacuum in a solvent-free, air-free environment.

Methylene meldrums acid derivatives of indoxyl and their cyclization reactions under flash vacuum pyrolysis conditions

Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2′-azidoacetophenone at 650 °C. Reaction of indoxyl with methoxymethylene Meldrums acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2-methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%). Georg Thieme Verlag Stuttgart · New York.

Reactions of Carboxylic Acids with "Phosphonium Anhydrides"

General considerations are outlined for a reagent to extract oxygen from organic molecules by an equivalent of dehydration.Reagents, (R3P+)2O, 2OTf-, were created for the purpose and subjected to a preliminary study.They were found to convert carboxylic acids readily and rapidly to anhydrides, esters, amides, amidines, benzimidazoles, and cyclic aryl ketones in good yields.