496-30-0

Basic information

• Product Name: 1,3-DIHYDRO-2H-INDOLE-2-THIONE
• Synonyms: 1,3-DIHYDRO-2H-INDOLE-2-THIONE;1H-Indole-2(3H)-thione;2,3-Dihydro-1H-indole-2-thione;2-Indolinethione;2H-Indole-2-thione, 1,3-dihydro- (9ci);Benzazoline-2-thione;Brn 0002992;1,3-Dihydro-indole-2-thione
• CAS NO: 496-30-0
• Molecular Formula: C₈H₇NS
• Molecular Weight: 149.21
• Mol File: 496-30-0.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 243℃
• Flash Point: 101℃
• Appearance: /
• Density: 1.27
• Vapor Pressure: 0.0322mmHg at 25°C
• Refractive Index: 1.692
• Solubility: Dichloromethane + Methanol, DMSO
• CAS DataBase Reference: 1,3-DIHYDRO-2H-INDOLE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIHYDRO-2H-INDOLE-2-THIONE(496-30-0)
• EPA Substance Registry System: 1,3-DIHYDRO-2H-INDOLE-2-THIONE(496-30-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 496-30-0(Hazardous Substances Data)

Usage

Uses

Indoline-2-thione is an intermediate in the synthesis of Brassilexin (B676870). Brassilexin is a novel sulphur-containing phytoalexin from Brassica Juncea L.

InChI:InChI=1/C8H7NS/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)

Upstream product

• 59-48-3 2-oxoindole 
• 120-72-9 indole 
• 13839-92-4 5,10-dihydro[1,2,3,4]tetrathiocino[5,6-b:8,7-b']diindole 
• 3289-82-5 1-hydroxyindole 
• 587-65-5 N-chloroacetyl-aniline 
• 110994-15-5 S-Ethynyl-N-phenyl-thiohydroxylamine 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 120105-52-4 indol-2-yl 2-nitrophenyl sulphide 
• 120-72-9 indole 
• 1484-19-1 3-ethyl-1H-indole 
• 91-56-5 indole-2,3-dione 
• 1131427-22-9 2-(4-methylbenzoylaminomethylthio)-1H-indole 
• 1131427-19-4 2-(4-chlorobenzoylaminomethylthio)-1H-indole 
• 1131427-24-1 2-(2-chlorobenzoylaminomethylthio)-1H-indole 
• 1131427-26-3 2-(2-methylbenzoylaminomethylthio)-1H-indole 
• 1202925-95-8 C₁₅H₁₃NOS 
• 1202925-93-6 C₁₅H₁₃NOS 
• 1202925-88-9 2-(4-methoxybenzylthio)-1H-indole 
• 32952-81-1 2-(benzylthio)-1H-indole 

Relevant articles and documents

Studies on fused indoles. I. Novel synthesis of 4-aminomethyltetrahydrothiopyrano[2,3-b]indoles through a thio-claisen rearrangement

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Preparation of Benzothiopyrano[2,3-b]indoles by thereaction of 1,3-dihydroindole-2-thiones with certain dienophiles

Benzothiopyrano[2,3-b]indoles were prepared by the cyclization of 1,3-dihydroindole-2-thiones with varions dienophiles. The 1,3-dihydroindole-2- thiones were readily synthesized by the reaction of oxindole with P2S5 followed by a piperidine-mediated condensation of the resulting thioindole with a suitable aromatic aldehyde.

Synthesis of 2-(Arylthio)indolenines via Chemoselective Arylation of Thio-Oxindoles with Arynes

A chemoselective S-arylation reaction of thio-oxindoles with arynes is presented. The reaction was performed under mild conditions and provided a straightforward synthesis of 2-(arylthio)indolenines in good to excellent yields. Besides, this simple operat

Nickel(ii)-catalyzed asymmetric thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles

A nickel(ii) catalyzed enantioselective thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles was realized with modified chiral N,N′-dioxide ligands, affording a variety of C3-substituted indole derivatives in high yields (up to 95%) with excellent enantioselectivities (up to 96% ee) under mild reaction conditions. A possible transition state model was proposed based on previous reports and the X-ray crystal structure of the catalyst.

One-pot mild and efficient synthesis of [1,3]thiazino[3,2-: A] indol-4-ones and their anti-proliferative activity

A base mediated environmentally benign one-pot efficient methodology has been developed for the synthesis of [1,3]thiazino[3,2-a]indol-4-ones using indoline-2-thiones and propiolate esters in aqueous medium. The conjugate addition of thiones first results in ethyl (3-(indol-2-yl)thio)acrylates in situ, which subsequently undergoes intramolecular cyclization to produce indole-fused thiazin-4-ones in good to excellent yields. The cytotoxic screening of the synthesized compounds using MTT assay revealed the anti-proliferative nature of these frameworks against triple negative breast cancer cell lines with the highest activity emanating from 4H-[1,3]thiazino[3,2-a]indol-4-one and 8-methyl-2-propyl-4H-[1,3]thiazino[3,2-a]indol-4-one compounds.