40800-64-4

Basic information

• Product Name: (3S)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one
• CAS NO: 40800-64-4
• Molecular Formula: C₉H₉NOS
• Molecular Weight: 179.2389
• Mol File: 40800-64-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 353.3°C at 760 mmHg
• Flash Point: 167.5°C
• Density: 1.28g/cm³
• Vapor Pressure: 3.62E-05mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: (3S)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one(40800-64-4)
• EPA Substance Registry System: (3S)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one(40800-64-4)

Safety Data

• Hazardous Substances Data: 40800-64-4(Hazardous Substances Data)

Usage

General Description

The chemical (3S)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one, also known as 3-Methylthio-3,4-dihydro-2H-1-benzopyran-2-one, is an organic compound with a molecular formula of C10H11NOS. It is a member of the class of compounds known as indoles, which are a large and diverse group of naturally occurring molecules with important biological and pharmaceutical properties. The methylsulfanyl group in this compound contributes to its unique chemical and physical properties. (3S)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one may have potential applications in drug discovery and development due to its structural features and biological activity.

Upstream product

• 29124-26-3 methanesulfinyl-acetic acid anilide 
• 16630-66-3 methyl 2-(methylthio)acetate 
• 62-53-3 aniline 
• 4455-14-5 ethyl 2-(methylsulfinyl)acetate 
• 4455-13-4 methylthioacetic acid ethyl ester 
• 3325-11-9 5-aminobenzotriazole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 68235-96-1 rac-3-chloroindolin-2-one 
• 5188-07-8 sodium thiomethoxide 
• 3265-29-0 3-diazo-indolin-2-one 
• 624-92-0 Dimethyldisulphide 
• 74-93-1 methylthiol 
• 1261171-20-3 2-oxindole-3-thione S-oxide 
• 10156-36-2 2-(methylsulfanyl)-N-phenylacetamide 

Downstream Products

• 57397-97-4 2-(N-allylamino)benzoic acid 
• 77336-52-8 5-allyl-5,10b-dihydro-10b-methylthio-11H-quinindolin-11-one 
• 861299-94-7 5-methoxy-2-methylamino-benzoic acid 
• 77336-51-7 2-methoxy-5-methyl-5,10b-dihydro-10b-methylthio-11H-quinindolin-11-one 
• 119-68-6 N-Methylanthranilic acid 
• 77415-04-4 5-methyl-5,10b-dihydro-10b-methylthio-11H-quinindolin-11-one 
• 120-72-9 indole 
• 799561-13-0 C₃₉H₄₀N₂O₄ 
• 799561-70-9 C₃₆H₃₆N₂O₄ 
• 799561-61-8 1-benzyl-3-methyl-3-methylsulfanyl-1,3-dihydroindol-2-one 
• 34943-91-4 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one 
• 799561-62-9 1,3-dimethyl-3-methylsulfanyl-1,3-dihydroindol-2-one 
• 40800-77-9 3-methyl-3-methylthioindol-2-one 
• 77336-50-6 2-chloro-5-methyl-5,10b-dihydro-10b-methylthio-11H-quinindolin-11-one 

Relevant articles and documents

A convenient modification of the Gassman oxindole synthesis

A modification of the Gassman oxindole synthesis is described that proceeds from anilines and ethyl (methylsulfinyl)acetate, using oxalyl chloride to activate the sulfoxide to facilitate the formation of the key N-S bonded intermediate. This procedure is particularly convenient for reactions carried out on smaller scales and for anilines that are susceptible to electrophilic halogenation.

N-Chlorophthalimide as a mild and efficient chlorination reagent in the Gassman ortho alkylation of aromatic amines. Synthesis of 3-(methylthio)oxindoles

A practical modification of the Gassman 3-(methylthio)oxindole synthesis is reported. In our method, substituted anilines and 2-(methylthio)acetamide were reacted under mild reaction conditions, in the presence of N-chlorophthalimide as a chlorinating agent to give α-amidosulfides, which, in the next step of the process, were cyclized to give 3-(methylthio)oxindoles. The method was successfully applied for the synthesis of the key intermediate, 2-(2-amino-3-benzoylphenyl)-2-(methylthio)acetamide, in the process of the preparation of nepafenac, a commonly used ophthalmic drug.

Synthesis of α-oxo-sulfines in the indole series

(Chemical Equation Presented) Oxindole was found to react readily with thionyl chloride to give (in an excellent yield) the isolable sulfine (13a), which on heating (refluxing acetonitrile) gave isoindigo (15a). The dark violet 3-sulfinatooxindole (13a) readily reacted with 2,3-dimethylbutadiene to give a colorless cyclo-adduct (14a). The sulfine also reacted readily with various nucleophilic reagents, thus, thioloacetic acid gave 3-carboxymethylthiolo- oxindole (23a).