10487-31-7

Basic information

• Product Name: 1-ISOPROPYL-1H-INDOLE-2,3-DIONE
• Synonyms: AKOS BBS-00001001;1-ISOPROPYL-1H-INDOLE-2,3-DIONE;1-isopropylindoline-2,3-dione
• CAS NO: 10487-31-7
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Mol File: 10487-31-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 74-76,5°C
• Boiling Point: 311.3°Cat760mmHg
• Flash Point: 137.5°C
• Appearance: /
• Density: 1.223g/cm³
• Vapor Pressure: 0.000569mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: 1-ISOPROPYL-1H-INDOLE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ISOPROPYL-1H-INDOLE-2,3-DIONE(10487-31-7)
• EPA Substance Registry System: 1-ISOPROPYL-1H-INDOLE-2,3-DIONE(10487-31-7)

Safety Data

• Hazardous Substances Data: 10487-31-7(Hazardous Substances Data)

Usage

General Description

1-ISOPROPYL-1H-INDOLE-2,3-DIONE, also known as isatin, is a heterocyclic organic compound with the chemical formula C10H9NO2. It is a white to off-white solid that is commonly used as a precursor in the synthesis of various pharmaceuticals, agrochemicals, and dyes. Isatin is also known for its diverse biological activities, including antibacterial, antiviral, antifungal, and anticancer properties. It has been studied for its potential use in the treatment of various diseases, including cancer and neurodegenerative disorders. Isatin is readily available and can be easily synthesized, making it a valuable chemical building block for the production of novel compounds with potential therapeutic applications.

InChI:InChI=1/C11H11NO2/c1-7(2)12-9-6-4-3-5-8(9)10(13)11(12)14/h3-7H,1-2H3

Upstream product

• 91-56-5 indole-2,3-dione 
• 107-08-4 1-iodo-propane 
• 75-30-9 2-iodo-propane 
• 16885-99-7 1-isopropyl-1H-indole 
• 1239867-53-8 2-(2-bromophenyl)-N-isopropylacetamide 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 1918-16-7 2-chloro-N-(1-methylethyl)-N-phenylacetamide 
• 161455-97-6 2-bromo-N-isopropyl-N-phenyl-acetamide 
• 924-44-7 glyoxylic acid ethyl ester 
• 768-52-5 N-Isopropylaniline 
• 75-26-3 isopropyl bromide 

Downstream Products

• 64788-47-2 N-isopropyl-1,3-dihydro-2H-indol-2-one 

Relevant articles and documents

Use of pyridinium chlorochromate and reusable polyaniline salt catalyst combination for the oxidation of indoles

A novel method is described herein for the simple, convenient and efficient oxidation of indoles to isatins using pyridinium chlorochromate with the aid of polyaniline salt catalyst at room temperature or at reflux in dichloroethane. Interestingly, oxidation of 3-alkyl indoles by this procedure gave 3-hydroxy 3-alkyl oxindoles. On the other hand, indol-3-alkanols gave mixtures of isatins and 3-formyl indoles. This is the first example of use of polyaniline as a catalyst in oxidation reaction.

A convenient methodology for the N-alkylation of isatin compounds

A simple, high yielding, methodology for the N-alkylation of substituted isatin derivatives using calcium hydride in DMF is detailed.

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.

Palladium-Catalyzed Cascade Hydrosilylation and Amino-Methylation of Isatin Derivatives

We demonstrate that using palladium acetate as a catalyst for reduction of DMF and isatin derivatives by hydrosilanes, a cascade hydrosilylation and amino-methylation reaction can be realized. With DMF as a reactant and a solvent, the in-situ generated siloxymethylamine intermediate, an adduct of DMF and hydrosilanes, smoothly participates in the successive stages, providing a serials of Si, N-functionalized indolin-2-ones in moderate to good yields. This strategy exhibits high chemoselectivity toward carbonyl moieties reduction among the substrates. (Figure presented.).

Palladium catalyzed divergent cycloadditions of vinylidenecyclopropane-diesters with methyleneindolinones enabled by zwitterionic π-propargyl palladium species

A palladium-catalyzed divergent synthesis of spirooxindoles fused with a five- or a six-membered ring by a cycloaddition reaction of vinylidenecyclopropane-diesters with methyleneindolinones was disclosed. This protocol features anin situgenerated unprecedented zwitterionic π-propargyl palladium species in cycloaddition reactions and a switchable process between (3+2) and (4+2) cycloadditions by changing the phosphine ligand.

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.