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

Description

5-Bromo-1-methyl-2-oxoindoline is an organic compound characterized by its indoline structure, which features a fused indole and pyrrole ring system. The molecule is distinguished by the presence of a bromine atom at the 5-position, a methyl group at the 1-position, and a 2-oxo (carbonyl) group. 5-Bromo-1-methyl-2-oxoindoline is known for its potential applications in various chemical and pharmaceutical processes due to its unique structural features.

Uses

Used in Organic Synthesis:
5-Bromo-1-methyl-2-oxoindoline is used as a valuable intermediate in the field of organic synthesis for the preparation of a range of complex organic molecules. Its unique structural features make it a versatile building block for the development of novel compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Bromo-1-methyl-2-oxoindoline is used as a key intermediate for the synthesis of symmetric cyclic indole-tetramers. These indole-tetramers have been found to possess significant biological activities, including potential applications in the treatment of various diseases and disorders.
Used in Chemical Research:
5-Bromo-1-methyl-2-oxoindoline is also utilized in chemical research as a starting material for the preparation of substituted oxindoles. These substituted oxindoles are important scaffolds in the development of new drugs and pharmaceutical agents, as they can exhibit a wide range of biological activities, such as anti-inflammatory, analgesic, and anti-cancer properties.

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

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 
• 1027233-55-1 5-Bromo-1-methyl-2-thioxo-2,3-dihydro-1H-indole-3-carboxylic acid phenylamide 
• 166882-70-8 5-[[4-[(2S,4R)-4-hydroxy-2-methyl-tetrahydropyran-4-yl]-2-thienyl]sulfanyl]-1-methyl-indolin-2-one 
• 256935-88-3 benzyl 1-methyl-oxindole-5-carboxylate 
• 1220696-38-7 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-indol-2-one 
• 1198594-08-9 2,5-diphenyl-1-methyl-1H-indole 
• 1323359-68-7 C₁₇H₁₄F₃NO₄S 
• 1323359-70-1 2-[(E)-1-ethoxybuta-1,3-dienyl]-5-(4-methoxyphenyl)-1-methyl-1H-indole 
• 1323359-94-9 4-{2-[(E)-1-ethoxybuta-1,3-dienyl]-1-methyl-1H-indol-5-yl}-N,N-dimethylbenzenamine 
• 1323359-71-2 (+/-)-1,2-dihydro-7-(4-methoxyphenyl)-1,4-dimethylcyclopenta[b]indol-3(4H)-one 
• 1323359-99-4 (+/-)-7-[4-(dimethylamino)phenyl]-1,2-dihydro-1,4-dimethylcyclopenta[b]indol-3(4H)-one 
• 1323359-73-4 (2E)-2-[(2,5-dihydro-4-methyl-5-oxofuran-2-yloxy)methylene]-1,2-dihydro-7-(4-methoxyphenyl)-1,4-dimethylcyclopenta[b]indol-3(4H)-one 
• 1323360-03-7 (2E)-2-[(2,5-dihydro-4-methyl-5-oxofuran-2-yloxy)methylene]-7-[4-(dimethylamino)phenyl]-1,2-dihydro-1,4-dimethylcyclopenta[b]indol-3(4H)-one 

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.