122750-25-8

Basic information

• Product Name: 6-Chloro-1-methyl-1H-indole-2,3-dione
• Synonyms: 6-Chloro-1-methyl-1H-indole-2,3-dione;6-CHLORO-1-METHYLINDOLINE-2,3-DIONE
• CAS NO: 122750-25-8
• Molecular Formula: C₉H₆ClNO₂
• Molecular Weight: 195.60244
• Mol File: 122750-25-8.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Chloro-1-methyl-1H-indole-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-1-methyl-1H-indole-2,3-dione(122750-25-8)
• EPA Substance Registry System: 6-Chloro-1-methyl-1H-indole-2,3-dione(122750-25-8)

Safety Data

• Hazardous Substances Data: 122750-25-8(Hazardous Substances Data)

Upstream product

• 6341-92-0 6-chloroisatin 
• 77-78-1 dimethyl sulfate 
• 1227290-75-6 N-(5-chloro-2-iodophenyl)methanamine 
• 155868-51-2 6-chloro-1-methyl-1H-indole 
• 17422-33-2 6-chloroindole 
• 108-42-9 3-chloro-aniline 
• 74-88-4 methyl iodide 
• 60711-15-1 N-methyl-N-(3-chlorophenyl)carboxamide 

Downstream Products

• 1455123-95-1 C₁₆H₁₂ClN₃OS 
• 1443041-74-4 (2S,5S)-dibenzhydryl 6'-chloro-1'-methyl-2'-oxo-5-vinyl-4,5-dihydro-3H-spiro[furan-2,3'-indoline]-3,3-dicarboxylate 
• 1604677-00-0 C₁₈H₁₂ClNO₃ 

Relevant articles and documents

Asymmetric Intermolecular Rauhut?Currier Reaction for the Construction of 3,3-Disubstituted Oxindoles with Quaternary Stereogenic Centers

A remote cross Rauhut?Currier reaction utilizing vinyl ketones and para-quinone methides derived from isatins was realized, which was successfully catalyzed using bifunctional phosphines, furnishing chiral 3,3-disubstituted oxindoles in excellent enantioselectivities and high yields. The mechanistic studies demonstrated the key role of the alkyl hydrogen of the vinyl ketones, which conceivably interacted with the para-quinone methide carbonyl group via the hydrogen bond, offering a new insight for the design of novel asymmetric reactions. (Figure presented.).

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.

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.