20870-90-0

Basic information

• Product Name: 5-Bromo-1-methyl-2-oxoindoline
• Synonyms: 5-Bromo-1-methyl-2-oxoindoline;5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one;5-broMo-1-Methylindolin-2-one;2H-Indol-2-one, 5-broMo-1,3-dihydro-1-Methyl-;5-Bromo-1-methyl-2-oxindole 97%;5-Bromo-1-methylindolin-2-one, 5-Bromo-1,3-dihydro-1-methyl-2H-indol-2-one;5-bromo-1-methyl-2-indolinone;5-bromo-1-methyl-3H-indol-2-one
• CAS NO: 20870-90-0
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.06992
• Mol File: 20870-90-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 132 °C
• Boiling Point: 418.1 °C at 760 mmHg
• Flash Point: 206.6 °C
• Appearance: /
• Density: 1.589 g/cm³
• Vapor Pressure: 3.37E-07mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-Bromo-1-methyl-2-oxoindoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1-methyl-2-oxoindoline(20870-90-0)
• EPA Substance Registry System: 5-Bromo-1-methyl-2-oxoindoline(20870-90-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 20870-90-0(Hazardous Substances Data)

Usage

Uses

5-Bromo-1-methyl-2-oxoindoline is a useful intermediate for organic synthesis. It is used as an intermediate in the preparation of symmetric cyclic indole-tetramers and some substituted oxindoles.

InChI:InChI=1/C9H8BrNO/c1-11-8-3-2-7(10)4-6(8)5-9(11)12/h2-4H,5H2,1H3

Upstream product

• 61-70-1 N-methyl-2-indolinone 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 74-88-4 methyl iodide 
• 6911-87-1 4-bromo-N-methylaniline 
• 1384521-02-1 2-diazo-N-(4-bromophenyl)-N-methylacetamide 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 38118-70-6 2-diazo-N-methyl-N-phenylacetamide 
• 100-61-8 N-methylaniline 
• 2058-72-2 5-bromo-1-methyl-1H-indole-2,3-dione 

Downstream Products

• 110376-44-8 5-bromo-3-(4-diethylamino-phenylimino)-1-methyl-indolin-2-one 
• 69736-60-3 5-bromo-1-methyl-indoline-2,3-dione-3-oxime 
• 1596355-35-9 ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate 

Relevant articles and documents

An atypical easy reductive cleavage of the conjugated CC bond in 1,1′-disubstituted isoindigos under the action of aqueous hydrazine hydrate

The reaction of diverse symmetrically-substituted isoindigo derivatives with 80% aqueous hydrazine hydrate is described. The influence of the structure of the substituent on either oxindole or isatin-3-hydrazone formation is discussed.

Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).

Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles

Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.