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

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

• 17630-76-1 5-chloroindole 2,3-dione 
• 77-78-1 dimethyl sulfate 
• 208177-08-6 (E)-1,2-Dichloro-N,N'-bis-(4-chloro-phenyl)-N,N'-dimethyl-ethene-1,2-diamine 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 79-37-8 oxalyl dichloride 
• 74-88-4 methyl iodide 
• 847550-39-4 5-chloro-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-methyl-1,3-dihydroindol-2-one 
• 872305-97-0 N-(4-chloro-phenyl)-N-methyl-2-oxo-acetamide 
• 65798-06-3 N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide 
• 106-47-8 4-chloro-aniline 
• 112398-75-1 5-chloro-1-methyl-1H-indole 
• 74-83-9 methyl bromide 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 26772-93-0 N-(4-chlorophenyl)-N-methylformamide 

Downstream Products

• 81913-00-0 5-Chloro-3-[(Z)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino]-1-methyl-1,3-dihydro-indol-2-one 
• 88114-36-7 3-(3'-Carboxyphenylthiosemicarbazono)-5-chloro-1-methyl-2-indolinone 
• 84496-09-3 ethyl 4-<<4'-(1,2-dihydro-1-methyl-5-chloro-2-oxo-3H-indol-3-ylideneamino)benzoyl>amino>benzoate 
• 84507-77-7 methyl 4-<<4'-(1,2-dihydro-1-methyl-5-chloro-2-oxo-3H-indol-3-ylideneamino)benzoyl>amino>benzoate 
• 84496-10-6 propyl 4-<<4'-(1,2-dihydro-1-methyl-5-chloro-2-oxo-3H-indol-3-ylideneamino)benzoyl>amino>benzoate 
• 84496-11-7 butyl 4-<<4'-(1,2-dihydro-1-methyl-5-chloro-2-oxo-3H-indol-3-ylideneamino)benzoyl>amino>benzoate 
• 106550-97-4 5-Chloro-1-methyl-3-[(Z)-4-((E)-styryl)-phenylimino]-1,3-dihydro-indol-2-one 
• 132558-42-0 5-Chloro-3-[(6-chloro-benzothiazol-2-yl)-hydrazono]-1-methyl-1,3-dihydro-indol-2-one 
• 14529-12-5 6-chloro-N-methylisatoic anhydride 

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.

Base-mediated allylation of N-2,2,2-trifluoroethylisatin ketimines and its application in aza-Prins reactions

The aza-Prins reaction of allylic imines triggered by N-2,2,2-trifluoroethylisatin ketimine is accomplished for the synthesis of spirooxindole derivatives involving trifluoromethyl group in the presence of TMSX. This cyclization reaction is operationally simple and proceeds under mild conditions using non-toxic reagents. Notably, while the previous our work could not be compatible with TMSX (X = Cl, I, etc) in one-pot process, this work describes successful aza-Prins reaction with TMSX (X = Cl, I, etc) via step-by-step process.

Decarboxylative Organocatalyzed Addition Reactions of Fluoroacetate Surrogates for the Synthesis of Fluorinated Oxindoles

Fluorinated malonic acid half thioesters (F-MAHTs) were used as thioester enolate equivalents in organocatalyzed addition reactions to isatins. The products from a range of different N-protected and nonprotected isatins were obtained under mild reaction conditions in high yields and enantioselectivities. The unique reactivity of the thioester moiety enabled diverse derivatization and allowed for the straightforward access to a fluorinated analogue of the anticancer agent (S)-YK-4-279, a therapeutically active compound against Ewing's sarcoma.

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.

Construction of 2-alkynyl aza-spiro[4,5]indole scaffolds: Via sequential C-H activations for modular click chemistry libraries

Herein, we have developed a strategy of sequential C-H activations of indole to construct novel 2-alkynyl aza-spiro[4,5]indole scaffolds, which incorporated both alkyne and spiro-units into indole. Gram-scale synthesis and a one-pot, three-step synthesis demonstrated the utility of this protocol. Hybrid conjugates with an oseltamivir derivative further offered a powerful tool for the construction of a versatile spiroindole-containing library via click chemistry. This journal is

3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom

A simple and efficient strategy has been established for the synthesis of δ-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and α,β-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.

Synthesis, characterization and anticancer activity of (5,1-substituted)-3-(indoline-4-(thiophene- 2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1h-imidazole-5-one derivatives

The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives (4a-j) to yield final compounds 5a-j. The organic potentials of the newly synthesized imidazole-5-one derivatives have been evaluated for their in vitro anticancer activity by MTT assay method. It against MCF-7 cells as comparison with doxorubicin popular drug. The synthesized compounds 5e, 5f and 5j exhibited excellent anticancer activity against MCF-7 cell lines.

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.

Design, synthesis, and biological evaluation of 1,2,3-triazole-linked triazino[5,6-b]indole-benzene sulfonamide conjugates as potent carbonic anhydrase I, II, IX, and XIII inhibitors

A series of 1,2,3-triazole-linked triazino[5,6-b]indole-benzene sulfonamide hybrids (6a– 6o) was synthesized and evaluated for carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity against the human (h) isoforms hCA I, II, XIII (cytosolic isoforms), and hCA IX (transmembrane tumor-associated isoform). The results revealed that the compounds 6a–6o exhibited Ki values in the low to medium nanomolar range against hCA II and hCA IX (Kis ranging from 7.7 nM to 41.3 nM) and higher Ki values against hCA I and hCA XIII. Compound 6i showed potent inhibition of hCA II (Ki = 7.7nM), being more effective compared to the standard inhibitor acetazolamide (AAZ) (Ki = 12.1 nM). Compounds 6b and 6d showed moderate activity against hCA XIII (Ki= 69.8 and 65.8 nM). Hence, compound 6i could be consider as potential lead candidate for the design of potent and selective hCA II inhibitors.

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.