320734-35-8

Basic information

• Product Name: 7-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE
• Synonyms: 7-CHLOROINDOLIN-2-ONE;7-BROMOOXINDOLE;7-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE;7-bromoindolin-2-one;7-Bromo-2-oxindole;7-BroMo-2-oxindole/7-BroMo-1,3-dihydro-2H-indol-2-one;7-Bromo-1,3-dihydro-2H-indol-2-one;7-chloro-2,3-dihydro-1H-indol-2-one
• CAS NO: 320734-35-8
• Molecular Formula: C₈H₆BrNO
• Molecular Weight: 212.04
• EINECS: 1312995-182-4
• Product Categories: blocks;Bromides;IndolesOxindoles;Indoline & Oxindole
• Mol File: 320734-35-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 194-200°C
• Boiling Point: 358.8 °C at 760 mmHg
• Flash Point: 170.8 °C
• Appearance: /
• Density: 1.666 g/cm³
• Vapor Pressure: 2.48E-05mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.22±0.20(Predicted)
• CAS DataBase Reference: 7-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE(320734-35-8)
• EPA Substance Registry System: 7-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE(320734-35-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 320734-35-8(Hazardous Substances Data)

Usage

Preparation

STEP A: Preparation of 7-chloro-3-hydrazono-oxindole. A solution of 25.0 g of 7-chloro-isatin in 250 ml of ethanol is refluxed for 24 hours, cooled, and precipitate recovered by filtering and washed once with ethanol and twice with pentane to obtain 7-chloro-3-hydrazono oxindole, m.p. 217-219℃. (decomp.).??STEP B: Preparation of 7-chloro-oxindole. To a solution of sodium ethoxide prepared by heating 5.5 g of sodium in 200 ml. of ethanol at 70°℃. is added 17 g of 7-chloro-3-hydrazono-oxindole over a period of 3.5 hours, and the resulting solution is heated at 70℃. for 24 hours. The solvent is evaporated in vacuo, the residue dissolved in water, acidified with 6 N-hydro chloric acid and the resulting precipitate recovered by filtering, washed three times with water, dried by suc tion and crystallized from methylene chloride/ether to obtain 7-chlorooxindole, 28-220℃.

InChI:InChI=1/C8H6BrNO/c9-6-3-1-2-5-4-7(11)10-8(5)6/h1-3H,4H2,(H,10,11)

Upstream product

• 20780-74-9 7-bromoisatin 
• 615-36-1 2-bromoaniline 
• 320734-34-7 4-(7-bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 320734-36-9 4-(7-bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 400629-31-4 2-(3-bromo-2-nitrophenyl)acetic acid 

Downstream Products

• 400629-20-1 7-[4-(1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]indolin-2-one 
• 100831-25-2 7-bromo-1-methylindolin-2-one 
• 31676-48-9 7-phenylindolin-2-one 

Relevant articles and documents

Enantioselective construction of the oxidized tryptophan fragment of proteasome inhibitors TMC-95A and TMC-95B

The oxidized tryptophan analogue 5, a proposed intermediate for a synthesis of the proteasome inhibitors TMC-95A and TMC-95B, is prepared using the condensation of oxindole 7 with the (R)-Garner aldehyde and stereoselective dihydroxylation of olefin 6 as key steps. (C) 2000 Elsevier Science Ltd.

Synthesis of novel 3-(benzothiazol-2-ylmethylene)indolin-2-ones

A mild method for the synthesis of 3-(benzothiazol-2-ylmethylene)indolin-2-ones via the aldol condensation of substituted indolin-2-ones and benzothiazole-2-carbaldehyde is described. This new procedure has significant advantages, such as mild conditions, high yields and simple work-up.

Selective reduction of carbonyl groups in the presence of low-valent titanium reagents

The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.