17630-76-1

Basic information

• Product Name: 5-Chloroisatin
• Synonyms: 5-Chloroindolin-2,3-dione;5-Chloroisatin ,98%;5-Chloroisatin,95%;Indole-2,3-dione, 5-chloro- (7CI,8CI);Isatin, 5-chloro- (6CI);NSC 135811;5-Chloroindolin-2,3-dione, 5-Chloro-1H-indole-2,3-dione;5-Chloroisatin 97%
• CAS NO: 17630-76-1
• Molecular Formula: C₈H₄ClNO₂
• Molecular Weight: 181.58
• EINECS: 241-614-0
• Product Categories: Indane/Indanone and Derivatives
• Mol File: 17630-76-1.mol
• Article Data: 84

Chemical Properties

• Melting Point: 254-258 °C(lit.)
• Appearance: /Powder
• Density: 1.3743 (rough estimate)
• Refractive Index: 1.5560 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.65±0.20(Predicted)
• Water Solubility: insoluble
• BRN: 383759
• CAS DataBase Reference: 5-Chloroisatin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloroisatin(17630-76-1)
• EPA Substance Registry System: 5-Chloroisatin(17630-76-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 17630-76-1(Hazardous Substances Data)

Usage

Chemical Properties

pale yellow to reddish or yellow-brownish powder

Uses

5-Chloroisatin is a reagent used in the synthesis of Schiff bases through the reaction with 2-methyl-4-nitroaniline or 4-amino-4,5-dihydro-1H-1,2,3-triazole-5-one.

General Description

5-Chloroisatin reacts with substituted 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones to yield Schiff bases.

InChI:InChI=1/C8H4ClNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)

Upstream product

• 85124-16-9 5-Chloroisatin 3-oxime 
• 25658-80-4 5-chloro-2,3-dihydroindole 
• 302-17-0 chloral hydrate 
• 106-47-8 4-chloro-aniline 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 91-56-5 indole-2,3-dione 
• 705288-14-8 5-chloro-2-nitro-mandelonitrile 
• 65798-06-3 N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide 
• 861381-87-5 5-chloro-2-methoxy-indol-3-one 
• 64-17-5 ethanol 
• 128-09-6 N-chloro-succinimide 
• 885964-67-0 C₁₃H₁₂ClNO₄ 
• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 412947-46-7 4-chloro-2-ethynylaniline 

Downstream Products

• 577-74-2 6-chloro-2-(3-fluoro-4-methoxy-phenyl)-3-methyl-quinoline-4-carboxylic acid 
• 391-21-9 6-chloro-2-(2-fluoro-5-methyl-phenyl)-quinoline-4-carboxylic acid 
• 386-08-3 6-chloro-2-(2-fluoro-5-methyl-phenyl)-3-phenyl-quinoline-4-carboxylic acid 
• 126088-20-8 6-chloro-2-(4-chlorophenyl)quinoline-4-carboxylic acid 
• 62482-28-4 6-chloroquinoline-2,4-dicarboxylic acid 
• 856177-13-4 6-chloro-3-hydroxy-quinoline-4-carboxylic acid 
• 6633-62-1 6-chloro-2-phenylquinoline-4-carboxylic acid 
• 103914-61-0 6-chloro-2-(p-tolyl)quinoline-4-carboxylic acid 
• 122262-53-7 6-chloro-2-(4-chloro-phenyl)-3-hydroxy-quinoline-4-carboxylic acid 
• 60434-13-1 5-chloro-1-methylindoline-2, 3-dione 
• 854867-53-1 6-chloro-2-(4-hydroxy-phenyl)-3-methyl-quinoline-4-carboxylic acid 
• 4743-17-3 5-Chloroisatoic anhydride 

Relevant articles and documents

5-Chloro- and 5,7-dichloroisatin by chlorination of isatin with trichloroisocyanuric acid

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REVERSIBLE MONOAMINE OXIDASE INHIBITORS IN THE INDOLINONE SERIES

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R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond

A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.

Synthesis and evaluation of tryptanthrins as antitumor agents

Here, an efficient and convenient method has been developed for the rapid preparation of N-substituted tryptanthrin analogues through the reaction of tryptanthrins and secondary amines under mild reaction conditions. All compounds were tested for their anti-tumor activity in cancer cell lines by MTT assay. The results showed that some of them exhibited anti-tumor activity against human tumor cell lines A549, HCT116, MDA-MB-231 with IC50 mean values at a low micromolar level. In particular, compound 3b induced G2/S cell cycle arrest and apoptosis in A549 cells dose-dependently.

A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered: N -sulfonyl-1,2,3-triazoles and indoles

An efficient and convenient protocol for the synthesis of a novel class of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles has been disclosed. The reaction proceeds via denitrogenative aza-vinyl rhodium carbene formation to give a carbonyl ylide, which with indole results in 1,3-dipolar cycloaddition followed by sequential semipinacol rearrangement/ring expansion/oxidation to produce azepino fused diindoles. The reaction shows a broad substrate scope giving up to 81% yield. Furthermore, reversible catalytic hydrogenation and photophysical studies were carried out to demonstrate the application of these molecules.