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
• Article Data: 15

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

Description

5-propan-2-yl-1H-indole-2,3-dione, commonly known as isatin, is a heterocyclic organic compound characterized by its distinct blue color and pungent odor. Derived from indole, isatin is a versatile chemical compound that is widely used in the synthesis of pharmaceuticals, organic materials, synthetic dyes, perfumes, and flavors. Its unique structure and diverse biological activities, including antibacterial, antiviral, anticancer, and anti-inflammatory properties, make isatin a valuable asset in the fields of organic chemistry and drug discovery.

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

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

Downstream Products

• 328396-77-6 1-phenyl-5-isopropylisatin 
• 1206485-35-9 C₁₈H₁₇NO₂ 

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.

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.