22942-87-6

Basic information

• Product Name: 2H-Indol-2-one, 3-bromo-1,3-dihydro-
• CAS NO: 22942-87-6
• Molecular Formula: C8H6BrNO
• Molecular Weight: 212.046
• Mol File: 22942-87-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2H-Indol-2-one, 3-bromo-1,3-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Indol-2-one, 3-bromo-1,3-dihydro-(22942-87-6)
• EPA Substance Registry System: 2H-Indol-2-one, 3-bromo-1,3-dihydro-(22942-87-6)

Safety Data

• Hazardous Substances Data: 22942-87-6(Hazardous Substances Data)

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 35438-06-3 diethyl (2-oxoindolin-3-yl) phosphate 
• 91-56-5 indole-2,3-dione 
• 28558-62-5 4-methyl-N'-(2-oxoindolin-3-ylidene)benzenesulfonohydrazide 
• 3265-29-0 3-diazo-indolin-2-one 

Downstream Products

• 19714-18-2 1,3-dihydro-3-(oxidophenylimino)-2H-indol-2-one 
• 26497-69-8 (Z)-3-[phenyl(phenylamino)methylidene]-1,3-dihydro-2H-indol-2-one 
• 262365-82-2 (Z)-3-[4-methoxyphenylamino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-one 
• 76369-69-2 N-(4-(dimethylamino)phenyl)-2-oxoindolin-3-imine oxide 
• 19714-18-2 (E)-N-(2-oxoindolin-3-ylidene)aniline oxide 

Relevant articles and documents

Formation of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones involving ring transformation of 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles

The reaction of 3-bromooxindole with substituted (hetero)aromatic thioamides in acetonitrile was studied. At room temperature the reaction preferably gives products of ring transformation i.e. 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles (3b-f,h) whereas at elevated temperature products of an Eschenmoser coupling reaction, i.e. 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones (2b-f), are formed exclusively. There exist only two exceptions (4-methoxy and 2-pyridinthioamide) in which the Eschenmoser coupling reaction always takes place giving 2a and 2g. Also N-methylation of the starting 3-bromooxindole completely prevents formation of thiazoles. The prepared thiazoles 3b-f are unstable in solution and they undergo slow ring transformation to 2b-f. The rate limiting step of this rearrangement involves cleavage of an intermediary thiirane ring, which is slowed down by electron-withdrawing substituents on the thioamide (ρ = ?1.15).

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

A CONVENIENT CONVERSION OF INDOLES TO 3,3-DIBROMOOXINDOLES AND THEN TO ISATINS

3-Bromoindoles, 3-unsubstituted indoles, or 3-formylindoles on treatment with NBS (2,3 or 4 molar equivalents, respectively) in t-butanol give 3,3-dibromooxindoles, and these readily yield the corresponding isatins on hydrolysis.