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

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 
• 695141-00-5 [2-(1-acetyl-1H-indol-3-yloxy)ethyl]dimethylamine 
• 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 
• 1922-77-6 2,2-diphenyl-1,2-dihydro-3H-indol-3-one 
• 1385032-02-9 2-amino-4,5-dihydro-4-(4-methylphenyl)pyrano[3,2-b]indole-3-carbonitrile 
• 1385032-05-2 2-amino-4-(4-chlorophenyl)-4,5-dihydropyrano[3,2-b]indole-3-carbonitrile 
• 1385032-06-3 2-amino-4-(2-chlorophenyl)-4,5-dihydropyrano[3,2-b]indole-3-carbonitrile 
• 1385032-07-4 2-amino-4,5-dihydro-4-(4-nitrophenyl)pyrano[3,2-b]indole-3-carbonitrile 

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.

Tautomerism of the Monohydroxy Derivatives of Five-Membered O, N, and S Heterocycles

The O-deuterated enolic tautomers 3-deuteroxybenzofuran, 3-deuteroxybenzothiophene, 3-deuteroxyindole, 3-deuteroxy-1-methylindole, 3-deuteroxyfuran, 3-deuteroxythiophene, 2-deuteroxybenzothiophene, and 2-deuteroxythiophene have been generated in solution in mixtures of CD3COCD3, CD3CN, or CD3SOCD3 with D2O by hydrolysis of their trimethylsilyl derivatives in the presence of DCl (1E-3 - 1E-4 M) and characterized by 1H NMR spectroscopy.Solutions of 3-hydroxypyrrole and of 3-hydroxy-1-methylpyrrole were obtained by methanolysis of their trimethylsilyl derivatives,evaporation of the methanol, and immediate dissolution in DMSO-d6.The carbocyclic analogues of the bicyclic heterocyclic enols 3-deuteroxyindene and 2-deuteroxyindene were also generated in solution.Attempts to prepare solutions of 2-deuteroxyfuran, 2-deuteroxypyrrole, and 2-deuteroxy-1-methylpyrrole were unsuccessful.The kinetics of ketonization of the OH forms of these enols have been investigated in water or aqueous acetonitrile solution.The equilibrium constants for the keto-enol tautomerism were also determined either by direct measurement when sufficient enol was present at equilibrium or as the ratio of the rate constant for enolization of the keto form to that for ketonization of the enol form, the former being determined by the iodine-trapping technique.The effect of solvent on the equilibrium constants was also studied.Sufficient data were available for the equilibrium between 3-hydroxyindole and 3-ketoindole for them to be analyzed by the four-parameter equation of Mills and Beak to yield an a value of 2.4 and a b value of -3.0.The pKas of the bicyclic enols were measured. 3-Hydroxybenzofuran and3-hydroxybenzothiophene are stronger acids than 3-hydroxyindole and 3-hydroxy-1-methylindole.The ketonization reactions are general acid and general base catalyzed and their mechanisms are discussed.