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
• Article Data: 8

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

General Description

2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione is a chemical compound with a molecular formula C16H13NO2. It is a yellow crystalline solid that is used in organic synthesis and pharmaceutical research. 2-(2,5-dimethylphenyl)-1H-isoindole-1,3(2H)-dione belongs to the class of isoindolones, which are heterocyclic compounds containing a isoindole moiety, which is a five-membered ring fused to an indole. It has potential applications in the development of new drugs, agrochemicals, and materials due to its unique structure and properties. Additionally, it has been used as a starting material for the synthesis of various biologically active compounds.

Upstream product

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

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.

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.

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.