19357-30-3

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-(2,4-dimethylphenyl)-
• CAS NO: 19357-30-3
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.285
• Mol File: 19357-30-3.mol

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2,4-dimethylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2,4-dimethylphenyl)-(19357-30-3)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-(2,4-dimethylphenyl)-(19357-30-3)

Safety Data

• Hazardous Substances Data: 19357-30-3(Hazardous Substances Data)

Usage

General Description

1H-Isoindole-1,3(2H)-dione, 2-(2,4-dimethylphenyl)-, also known as 2-(2,4-dimethylphenyl)isoindoline-1,3-dione, is a chemical compound with the molecular formula C16H13NO2. It is a yellow to brown crystalline solid that is commonly used as a reagent in organic synthesis. 1H-Isoindole-1,3(2H)-dione, 2-(2,4-dimethylphenyl)- is often utilized in the production of pharmaceuticals and agrochemicals, as well as in the creation of dyes and pigments. It is also known for its ability to act as a nitrile oxide when reacted with nitrosating agents. The compound has an aromatic ring structure and is considered to be relatively stable under normal conditions.

Upstream product

• 85-44-9 phthalic anhydride 
• 95-68-1 2,4-Xylidine 
• 88-95-9 Phthaloyl dichloride 
• 136918-14-4 phthalimide 
• 3481-09-2 N-chlorophthalimide 
• 108-38-3 m-xylene 
• 10026-13-8 phosphorus pentachloride 
• 547762-03-8 N,N'-bis-(2,4-dimethyl-phenyl)-phthalamide 

Relevant articles and documents

Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis of various isoindoline-1,3-dione derivatives

An environmentally friendly method is described for the synthesis of various isoindoline-1,3-dione derivatives from the reaction of phthalic anhydride with aromatic/aliphatic amines in ethanol at 80 °C by phthalimide-N-sulfonic acid as an efficient heterogeneous acid catalyst. Some advantages include the metal-free and environmentally friendly protocol, simple operation and reusable processes, easy recovery, short reaction times, and high yields.

Asymmetric Synthesis of Indoline from Achiral Phthalimide Involving Crystallization-Induced Deracemization

Asymmetric synthesis was performed by combining the photochemical reaction of an achiral substrate followed by crystallization-induced deracemization. The results indicated that a fused indoline produced by photochemical intramolecular δ-hydrogen abstraction and cyclization of N-(5-chloro-2-methylphenyl)phthalimide crystallized as a racemic conglomerate. Since this substrate has an aminal skeleton, racemization involving a ring-opening and ring-closing equilibrium process occurred under suitable conditions. Efficient racemization was observed in acetone containing a catalytic base, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Crystallization-induced dynamic deracemization by Viedma ripening from racemic indoline was performed with an excellent enantioselectivity of 99 % ee. Furthermore, one-pot asymmetric synthesis of the indoline was achieved by the photochemical reaction of achiral phthalimide followed by continuous attrition-enhanced deracemization converging to 99 % ee of enantiomeric crystals. This is the first example of asymmetric expression and amplification by photochemical hydrogen abstraction and crystallization-induced dynamic deracemization.

Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes

In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.

Regioselective gold-catalyzed oxidative C-N bond formation

A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic aromatic metalation patterns.

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis

The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.

Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization

The development of a novel intermolecular oxidative amination reaction, a synthetic transformation that involves the simultaneous functionalization of both a N-H and C-H bond, is described. The process, which is mediated by an I(III) oxidant and contains no metal catalysts, provides a rapid and green method for synthesizing protected anilines from simple arenes and phthalimide. Mechanistic investigations indicate that the reaction proceeds via nucleophilic attack of the phthalimide on an aromatic radical cation, as opposed to the electrophilic aromatic amination that has been reported for other I(III) amination reactions. The application of this new reaction to the synthesis of a variety of substituted aniline derivatives is demonstrated.

Influence of the steric hindrance of the aryl group of pentavalent triarylbismuth derivatives in ligand coupling reactions

Tris(ortho-tolyl)bismuth dichloride derivatives react with nucleophiles under basic conditions to give good to high yields of the C-arylated substrates. Under the same conditions, trimesitylbismuth dichloride affords only poor yields of the C-mesitylated substrates. Similar influence of the substitution pattern of tris(ortho-tolyl)bismuth diacetate derivatives was observed in the copper-catalysed arylation of hydroxyl or amino groups.