60434-13-1

Basic information

• Product Name: 5-chloro-1-methyl-1H-indole-2,3-dione
• Synonyms: 5-chloro-1-methyl-1H-indole-2,3-dione;1-Methyl-5-chloroindoline-2,3-dione;5-Chloro-1-methylindoline-2,3-dione;Einecs 262-231-5;5-chloro-1-methyl-1H-indole-2,3-dione(SALTDATA: FREE);5-Chloro-1-methylisatin
• CAS NO: 60434-13-1
• Molecular Formula: C9H6ClNO2
• Molecular Weight: 195.60244
• EINECS: 262-231-5
• Mol File: 60434-13-1.mol
• Article Data: 101

Chemical Properties

• Melting Point: 175.0 to 179.0 °C
• Boiling Point: 344.9 °C at 760 mmHg
• Flash Point: 162.4 °C
• Appearance: /
• Density: 1.454 g/cm³
• Vapor Pressure: 6.39E-05mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-chloro-1-methyl-1H-indole-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-1-methyl-1H-indole-2,3-dione(60434-13-1)
• EPA Substance Registry System: 5-chloro-1-methyl-1H-indole-2,3-dione(60434-13-1)

Safety Data

• Hazardous Substances Data: 60434-13-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6ClNO2/c1-11-7-3-2-5(10)4-6(7)8(12)9(11)13/h2-4H,1H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 17630-76-1 5-chloroindole 2,3-dione 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 
• 41192-33-0 5-chloro-1-methylindolin-2-one 
• 131543-46-9 Glyoxal 
• 932-96-7 N-methyl(p-chloroaniline) 
• 77-78-1 dimethyl sulfate 
• 74-87-3 methylene chloride 
• 1015230-88-2 N-(4-chlorophenyl)-N-methyl-3-phenylprop-2-ynamide 
• 26663-50-3 5-chloro-1-methylindoline 
• 112398-75-1 5-chloro-1-methyl-1H-indole 
• 33280-23-8 N-(4-chlorophenyl)-N-methyl-2-bromoacetamide 

Downstream Products

• 33280-14-7 5-chloro-2-methylamino-benzoic acid 

Relevant articles and documents

New spiroindolinones bearing 5-chlorobenzothiazole moiety

In this study, 5-chloro-3H-spiro-[1,3-benzothiazole-2,3'-indole]-2'(1'H)-one derivatives 3a-l were synthesized by the reaction of 1H-indole-2,3-diones 1a-l with 2-amino-4-chlorothiophenol 2 in ethanol. 3a-l were tested for their abilities to inhibit lipid peroxidation (LP), scavenge DPPH? and ABTS?+ radicals, and to reduce Fe3+ to Fe2+. Most of the tested compounds exhibited potent scavenging activities against ABTS?+ radical, reducing powers and strong inhibitory capacity on LP. 3a, 3d, 3e, 3h, 3j and 3k chosen as prototypes were evaluated in the National Cancer Institute's in vitro primary anticancer assay. The greatest growth inhibitions were observed against a non-small cell lung cancer cell line HOP-92 for R1-fluoro substituted 3d and a renal cancer cell line RXF-393 for R-chloro substituted 3e in the primary screen.

Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors

Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.

Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles

An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.