40101-43-7

Basic information

• Product Name: 2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione
• Synonyms: 2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione;2-(2,5-dimethylphenyl)phthalimide
• CAS NO: 40101-43-7
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.27992
• Mol File: 40101-43-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione(40101-43-7)
• EPA Substance Registry System: 2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione(40101-43-7)

Safety Data

• Hazardous Substances Data: 40101-43-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione is used as a starting material for the synthesis of various biologically active compounds. Its unique structure and properties make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione is used as an intermediate in the synthesis of complex organic molecules. Its versatile chemical properties allow it to be incorporated into a wide range of compounds, making it a valuable tool in organic chemistry.
Used in Agrochemical Development:
2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione has potential applications in the development of new agrochemicals. Its unique structure and properties can be harnessed to create novel compounds with improved efficacy and selectivity in agricultural applications.
Used in Material Science:
2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione can be used in the development of new materials with unique properties. Its heterocyclic structure and chemical versatility make it a promising candidate for the creation of advanced materials with applications in various industries.

Upstream product

• 106-42-3 para-xylene 
• 3481-09-2 N-chlorophthalimide 
• 5672-90-2 N-(trifluoromethyl)acyloxyphthalimide 
• 524-38-9 N-hydroxyphthalimide 
• 136918-14-4 phthalimide 
• 71-43-2 benzene 
• 95-78-3 2,5-Dimethylaniline 
• 88-95-9 Phthaloyl dichloride 
• 85-44-9 phthalic anhydride 

Downstream Products

• 95-78-3 2,5-Dimethylaniline 

Relevant articles and documents

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.

Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides

The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.

N -aminopyridinium salts as precursors for N-centered radicals - Direct amidation of arenes and heteroarenes

Readily prepared N-aminopyridinium salts are valuable precursors for the generation of N-centered radicals. Reduction of these salts by single electron transfer allows for clean generation of amidyl radicals. It is shown that direct radical C-H amination of heteroarenes and arenes can be achieved with N-aminopyridinium salts under mild conditions by using photoredox catalysis.

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.

N-acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes

This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.

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.

Intermolecular oxidative C-N bond formation under metal-free conditions: Control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation

A new synthetic approach toward intermolecular oxidative C-N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.