66440-60-6

Basic information

• Product Name: 1,5-DIMETHYLINDOLINE-2,3-DIONE
• Synonyms: 1,5-DIMETHYLINDOLINE-2,3-DIONE;1,5-dimethyl-1H-indole-2,3-dione(SALTDATA: FREE);1,5-dimethyl-1H-indole-2,3-dione
• CAS NO: 66440-60-6
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Mol File: 66440-60-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 326.1°Cat760mmHg
• Flash Point: 153.3°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 0.00022mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: 1,5-DIMETHYLINDOLINE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIMETHYLINDOLINE-2,3-DIONE(66440-60-6)
• EPA Substance Registry System: 1,5-DIMETHYLINDOLINE-2,3-DIONE(66440-60-6)

Safety Data

• Hazardous Substances Data: 66440-60-6(Hazardous Substances Data)

Usage

Description

1,5-Dimethylindoline-2,3-dione is an organic compound with the molecular formula C10H9NO2. It is a derivative of indoline, which is a part of the larger family of nitrogen-containing heterocycles. 1,5-DIMETHYLINDOLINE-2,3-DIONE is characterized by its unique chemical structure, featuring two methyl groups at the 1st and 5th positions and a dione group at the 2nd and 3rd positions.

Uses

1. Used in Pharmaceutical Industry:
1,5-Dimethylindoline-2,3-dione is used as an intermediate compound for the synthesis of Spiro-epoxidized Indole-cyclopentenobutyrolactone compounds. These compounds have potential applications in the development of novel pharmaceuticals, particularly in the area of cancer research and treatment. The unique structure of 1,5-Dimethylindoline-2,3-dione allows for the creation of complex molecular architectures that can target specific biological pathways involved in cancer cell growth and proliferation.
2. Used in Chemical Research:
1,5-Dimethylindoline-2,3-dione can also be utilized in various chemical research applications, such as the study of reaction mechanisms, the development of new synthetic methods, and the exploration of novel chemical properties. Its unique structure makes it an interesting candidate for researchers looking to understand the behavior of nitrogen-containing heterocycles and their potential applications in various fields.

InChI:InChI=1/C10H9NO2/c1-6-3-4-8-7(5-6)9(12)10(13)11(8)2/h3-5H,1-2H3

Upstream product

• 27816-53-1 1,5-dimethyl-1H-indole 
• 1015230-86-0 N-(4-methylphenyl)-N-methyl-3-phenylpropiolamide 

Downstream Products

• 81912-99-4 3-[(Z)-1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino]-1,5-dimethyl-1,3-dihydro-indol-2-one 
• 106550-96-3 1,5-Dimethyl-3-[(Z)-4-((E)-styryl)-phenylimino]-1,3-dihydro-indol-2-one 
• 132558-41-9 3-[(6-Chloro-benzothiazol-2-yl)-hydrazono]-1,5-dimethyl-1,3-dihydro-indol-2-one 
• 1084893-09-3 1,5-dimethyl-1H-indole-2,3-dione 3-(N-allylthiosemicarbazone) 
• 1084893-12-8 1,5-dimethyl-1H-indole-2,3-dione 3-(N-benzylthiosemicarbazone) 
• 1084893-16-2 1,5-dimethyl-1H-indole-2,3-dione 3-[N-(4-nitrophenyl)thiosemicarbazone] 
• 1084893-13-9 1,5-dimethyl-1H-indole-2,3-dione 3-[N-(4-fluorophenyl)thiosemicarbazone] 
• 1084893-15-1 1,5-dimethyl-1H-indole-2,3-dione 3-[N-(3-bromophenyl)thiosemicarbazone] 
• 1084893-14-0 1,5-dimethyl-1H-indole-2,3-dione 3-[N-(2-bromophenyl)thiosemicarbazone] 
• 1084893-10-6 1,5-dimethyl-1H-indole-2,3-dione 3-(N-butylthiosemicarbazone) 

Relevant articles and documents

Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization

A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H functionalization strategy, which enables the formation of one C–C bond and multiple C–O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.

Palladium-Catalyzed Oxidation of Indoles to Isatins by tert -Butyl Hydroperoxide

The combination of a Pd catalyst and tert -butyl hydroeroxide (TBHP) is a powerful catalytic system for many types of oxidative transformations. Here, we report that a Pd/TBHP system facilitates the oxidation of indoles with a range of functionalities to give the corresponding isatin derivatives in good yields.

Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch

An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.