150560-58-0

Basic information

• Product Name: 5-propan-2-yl-1H-indole-2,3-dione
• Synonyms: 5-propan-2-yl-1H-indole-2,3-dione;5-Isopropylisatin;5-isopropyl-1H-indole-2,3-dione(SALTDATA: FREE);5-Isopropylindoline-2,3-dione;11J-308S;1H-Indole-2,3-dione, 5-isopropyl-;ZINC03276921
• CAS NO: 150560-58-0
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.22
• Mol File: 150560-58-0.mol

Chemical Properties

• Melting Point: 140 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.2g/cm³
• Refractive Index: 1.568
• Storage Temp.: 2-8°C
• PKA: 9.81±0.20(Predicted)
• CAS DataBase Reference: 5-propan-2-yl-1H-indole-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-propan-2-yl-1H-indole-2,3-dione(150560-58-0)
• EPA Substance Registry System: 5-propan-2-yl-1H-indole-2,3-dione(150560-58-0)

Safety Data

• Statements: 36
• Safety Statements: 26
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 150560-58-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-propan-2-yl-1H-indole-2,3-dione is used as a key intermediate in the synthesis of various pharmaceuticals for its diverse biological activities. Its antibacterial, antiviral, anticancer, and anti-inflammatory properties make it a promising candidate for the development of new drugs to treat a wide range of diseases.
Used in Organic Chemistry:
In the field of organic chemistry, 5-propan-2-yl-1H-indole-2,3-dione is used as a versatile building block for the synthesis of complex organic molecules. Its unique structure allows for various chemical reactions, making it a valuable compound for the creation of new organic materials with potential applications in various industries.
Used in Dye Production:
5-propan-2-yl-1H-indole-2,3-dione is used as a starting material in the production of synthetic dyes due to its distinct blue color. Its chemical properties enable the development of dyes with specific characteristics, such as color intensity and stability, for use in various applications, including textiles, plastics, and printing inks.
Used in Perfumery:
In the perfumery industry, 5-propan-2-yl-1H-indole-2,3-dione is used as a component in the creation of unique fragrances. Its pungent odor and chemical properties contribute to the development of distinct scents that can be used in perfumes, colognes, and other fragrance products.
Used in Flavor Industry:
5-propan-2-yl-1H-indole-2,3-dione is used in the flavor industry for its ability to impart specific taste profiles to food and beverage products. Its unique chemical structure allows for the development of flavors that can enhance the taste and aroma of various products, contributing to a more enjoyable consumer experience.

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

Upstream product

• 201230-82-2 carbon monoxide 
• 68701-52-0 isonitrosoaceto-p-isopropylanilide 
• 99-88-7 4-Isopropylaniline 
• 51605-97-1 2-bromo-4-isopropylaniline 
• 79-37-8 oxalyl dichloride 
• 302-17-0 chloral hydrate 
• 1421739-77-6 2-[(benzyloxy)imino]-N-[4-(propan-2-yl)phenyl]acetamide 

Downstream Products

• 328396-77-6 1-phenyl-5-isopropylisatin 
• 1404437-62-2 N-(4-isopropyl-2-(3-oxo-3,4-dihydroquinoxalin-2-yl)phenyl)thiophene-2-carboxamide 
• 1424209-42-6 9-isopropyl-4,5,6,7-tetraphenylazepino[3,2,1-hi]indole-1,2-dione 
• 1206485-35-9 C₁₈H₁₇NO₂ 
• 847138-14-1 3-{[4-(4-bromo-phenyl)-thiazol-2-yl]-hydrazono}-5-isopropyl-1,3-dihydro-indol-2-one 

Relevant articles and documents

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.

A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles

A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.

METHOD FOR PRODUCING ISATIN COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an isatin compound useful as raw materials for various medical and agrochemical products and dyes, in high yield, with high purity, at low cost, and by simple operation. SOLUTION: An method for producing an isatin compound includes the reaction of an isonitrosoacetanilide compound represented by formula (1) at 15-60°C with sulfuric acid of 75% or more in concentration [R is H, a halogen atom or a linear/branched/cyclic alkyl group; n is an integer of 1-4]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Synthesis of diverse isatins: Via ring contraction of 3-diazoquinoline-2,4-diones

An efficient synthesis of diverse isatin derivatives was accomplished by a copper-mediated reaction of 3-diazoquinoline-2,4-diones via ring contraction through domino Wolff rearrangement, decarboxylation, bromination, substitution, and dehydration. This protocol has several advantages as a one-pot procedure, with functional group tolerance, and high yield.

Design, synthesis, and biological evaluation of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetate derivatives as anti-proliferative agents through ROS-induced cell apoptosis

A novel class of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetate derivatives were designed and synthesized as potent anti-proliferative agents. Most of these compounds showed potent anti-proliferative activity against some tumor cell lines, including SK-BR-3, MDA-MB-231, HCT-116, SW480, Ovcar-3, HL-60, Saos-2 and HepG2. Compounds 8c and 11h were identified as the most potent ones, while HL-60, HCT116 and MDA-MB-231 were the most sensitive cell lines. Mechanistic study revealed that compound 8c enhanced reactive oxygen species level by inhibiting TrxR and then induced apoptosis by activating apoptosis proteins, bax and cleaved-caspase 3 in HCT116?cells. Preliminary SAR analysis indicated that modifications of the double bond and ester group made great effects on the anti-proliferative activity. Our findings suggested that it was worth further studies on the antitumor potency of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetates.

Synthesis of substituted isatins

Isatins are valuable intermediates for heterocyclic chemistry. Most of the common methods for their production are less than adequate when the number and lipophilicity of substituents on the targeted isatin are increased. Our group desired such molecules

H-β zeolite: An efficient, reusable catalyst for one-pot synthesis of isatins from anilines

We describe a simple and highly efficient procedure for the single-step preparation of isatins from the commercially available anilines using H-β zeolite as a truly heterogeneous catalyst. H-β zeolite is readily separated from reaction mixture by simple filtration and reused several times without considerable loss of activity.

Methods and Compositions for Selectin Inhibition

The present teachings relate to novel compounds of formula I: wherein the constituent variables are as defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selecting. Methods for treating or preventing selectin-mediated disorders are provided, which include administration of these compounds in a therapeutically effective amount.

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists

Leukocyte recruitment of sites of inflammation and tissue injury involves leukocyte rolling along the endothelial wall, followed by firm adherence of the leukocyte, and finally transmigration of the leukocyte across cell junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis. High-throughput screening of the Wyeth chemical library identified the quinoline salicylic acid class of compounds (1) as antagonists of P-selectin, with potency in in vitro and cell-based assays far superior to that of sLex. Through iterative medicinal chemistry, we identified analogues with improved P-selectin activity, decreased inhibition of dihydrooratate dehydrogenase, and acceptable CYP profiles. Lead compound 36 was efficacious in the rat AIA model of rheumatoid arthritis.

PTEN INHIBITORS

The therapeutic use of inhibitors of PTEN activity in the treatment of PTEN-mediated diseases, conditions, and injuries is disclosed.