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

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

Uses

Used in Pharmaceutical Industry:
3H-indol-3-one is used as a pharmaceutical agent for its antimicrobial, antioxidant, and anti-inflammatory properties, contributing to the development of new treatments for various diseases.
Used in Cosmetic Industry:
In the cosmetic industry, 3H-indol-3-one is utilized for its beneficial properties, which may include antioxidant and anti-inflammatory effects, to improve skin health and provide protective effects against environmental stressors.
Used in Textile Industry:
3H-indol-3-one is used as a precursor in the synthesis of indigo dye, which is a significant component in the textile industry for creating vibrant blue colors in fabrics, maintaining its historical importance in textile dyeing.
Used in Research and Development:
3H-indol-3-one is employed in research settings for studying its potential applications in the treatment of various diseases, including cancer and neurodegenerative disorders, as it continues to be explored for novel therapeutic uses.

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 
• 16714-26-4 1-(2-azido-phenyl)-ethanone 
• 120-72-9 indole 
• 4127-53-1 3-methylbenzo[c]isoxazole 
• 6245-93-8 3-hydroxy-1H-indole-2-carboxylic acid 

Downstream Products

• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 3265-35-8 indoline-2,3-dione-2-oxime 
• 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 
• 1385032-07-4 2-amino-4,5-dihydro-4-(4-nitrophenyl)pyrano[3,2-b]indole-3-carbonitrile 
• 790693-63-9 2-amino-4,5-dihydro-4-phenylpyrano[3,2-b]indole-3-carbonitrile 
• 1385032-01-8 2-amino-4,5-dihydro-4-(4-methoxyphenyl)pyrano[3,2-b]indole-3-carbonitrile 
• 1385032-03-0 2-amino-4-(4-bromophenyl)-4,5-dihydropyrano[3,2-b]indole-3-carbonitrile 
• 1385032-04-1 2-amino-4-(2-bromophenyl)-4,5-dihydropyrano[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.

Indigo dye production by enzymatic mimicking based on an iron(III)porphyrin

A novel indigo synthesis is based on a simple and cost-effective model system of the enzymes involved in the natural and biocatalytic productions. The method considers the oxidation of indole by hydrogen peroxide, being catalyzed by an iron(III)porphyrin in ethanol, as solvent, and no other additives. The yields of indigo and of the other oxidized indolinoid derivatives were found to be dependent on the metalloporphyrin system used and on the control of the oxidation conditions. Significant reductions of the environmental impact relatively to the present industrial production and of the costs relatively to the biocatalytic methodologies were obtained. The enhanced indigo production in the presence of the iron(III)porphyrin-ethanol catalytic system relatively to the manganese(III)porphyrin-acetonitrile system can be rationalized by the formation of different active species in the two systems.

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.

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.

REVERSIBLE CARBON PROTONATION IN THE HYDROLYSIS OF HETEROCYCLIC ENOL METHYL ETHERS

The kinetics of the hydronium-ion catalysed hydrolysis of the following heterocyclic methyl enol ethers have been measured: 3-methoxybenzofuran, 3-methoxybenzothiophene, 3-methoxyindole, 3-methoxy-1-methylindole, 3-methoxyfuran, 3-methoxythiophene, and 2-methoxythiophene.On the basis of the solvent isotope effect kH/kD = 3.08 and the failure to detect deuterium exchange when the solvent was CD3CN:D2O (9:1 v/v) it was concluded that the rate limiting step in the hydrolysis of 3-methoxybenzofuran is C-protonation.The effect of the ring-oxygen atom was measured by comparing the rate of hydrolysis of 3-methoxybenzofuran with that of 3-methoxyindene which occurs 2100 times faster.In contrast to the behaviour of 3-methoxybenzofuran the isotope effects, kH/kD, for the hydrolyses of 3-methoxyfuran, 3-methoxythiophene, 3-methoxyindole, 3-methoxy-1-methylindole and 2-methoxythiophene are ca 0.4 - 0.5 and deuterium exchange is much faster than hydrolysis when the solvent is CD3CN:D2O (9:1 v/v).It was therefore concluded that with these compound C-protonation is rapid and reversible and that slow step is attack by water on the intermediate cation.

THE TAUTOMERISM OF HYDROXY DERIVATIVES OF FIVE-MEMBERED OXYGEN, NIRTOGEN, AND SULFUR HETEROCYCLES

The unstable enolic tautomers 3-hydroxyfuran, 2- and 3-hydroxy-thiophene, 3-hydroxy-pyrrole, 3-hydroxy-1-methyl-pyrrole and their benzo-derivatives have been generated in solution and the rate and equilibrium constants for their ketoization determined.