2464-33-7

Basic information

• Product Name: 2-(2-methylphenyl)-1H-isoindole-1,3(2H)-dione
• Synonyms: 1H-isoindole-1,3(2H)-dione, 2-(2-methylphenyl)-; 2-Phthalimido-toluene; Phthalimide, N-o-tolyl-,
• CAS NO: 2464-33-7
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.2533
• Mol File: 2464-33-7.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 398.3°C at 760 mmHg
• Flash Point: 183.4°C
• Density: 1.296g/cm³
• Vapor Pressure: 1.49E-06mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 2-(2-methylphenyl)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-methylphenyl)-1H-isoindole-1,3(2H)-dione(2464-33-7)
• EPA Substance Registry System: 2-(2-methylphenyl)-1H-isoindole-1,3(2H)-dione(2464-33-7)

Safety Data

• Hazardous Substances Data: 2464-33-7(Hazardous Substances Data)

Usage

Molecular weight

309.32 g/mol

Chemical structure

2-(2-methylphenyl)-1H-isoindole-1,3(2H)-dione

Derived from

Qing Dai

Known as

Meisoindigo

Type of compound

Synthetic compound

Mechanism of action

Inhibits the growth and proliferation of cancer cells and induces apoptosis (programmed cell death)

Properties

Potent antitumor agent, anti-inflammatory, immunosuppressive

Cancer types treated

Leukemia, breast cancer, lung cancer, chronic myelogenous leukemia

Potential use

In combination with other anticancer drugs to enhance their effectiveness

Upstream product

• 3481-09-2 N-chlorophthalimide 
• 108-88-3 toluene 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 57365-06-7 2-<2-(bromomethyl)phenyl>-1H-isoindole-1,3(2H)-dione 
• 4870-19-3 2-o-toluidino-isoindoline-1,3-dione 
• 85-44-9 phthalic anhydride 
• 617-07-2 N,N'-bis(2-methylphenyl)urea 
• 1074-82-4 potassium phtalimide 
• 10468-64-1 o-tolyl isocyanide 
• 88-67-5 2-Iodobenzoic acid 
• 609-67-6 2-Iodobenzoyl chloride 
• 64-18-6 formic acid 
• 62303-06-4 N-(2-methylphenyl)-o-iodobenzamide 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Downstream Products

• 1025893-22-4 2,2,2-Trifluoro-N-methyl-N-{2-[1-(3-methyl-pyridin-2-yl)-1,4,5,6-tetrahydro-cyclopentaimidazole-2-sulfinylmethyl]-phenyl}-acetamide 
• 1026940-71-5 N-Ethyl-2,2,2-trifluoro-N-{2-[1-(3-methoxy-pyridin-2-yl)-1H-imidazole-2-sulfinylmethyl]-phenyl}-acetamide 
• 1026643-28-6 2,2,2-Trifluoro-N-methyl-N-{2-[1-(3-methyl-pyridin-2-yl)-1,4,5,6-tetrahydro-cyclopentaimidazol-2-ylsulfanylmethyl]-phenyl}-acetamide 
• 1027827-29-7 N-Ethyl-2,2,2-trifluoro-N-{2-[1-(3-methoxy-pyridin-2-yl)-1H-imidazol-2-ylsulfanylmethyl]-phenyl}-acetamide 
• 1026740-62-4 2-{2-[1-(3-Methoxy-pyridin-2-yl)-1H-imidazole-2-sulfinylmethyl]-phenyl}-isoindole-1,3-dione 
• 1027532-18-8 2,2,2-Trifluoro-N-{2-[1-(3-methoxy-pyridin-2-yl)-1H-imidazole-2-sulfinylmethyl]-phenyl}-N-methyl-acetamide 
• 1026631-90-2 2,2,2-Trifluoro-N-{2-[1-(3-methyl-pyridin-2-yl)-1,4,5,6-tetrahydro-cyclopentaimidazol-2-ylsulfanylmethyl]-phenyl}-acetamide 
• 1026731-17-8 2-{2-[1-(3-Methoxy-pyridin-2-yl)-1H-imidazol-2-ylsulfanylmethyl]-phenyl}-isoindole-1,3-dione 
• 1026484-52-5 N-Ethyl-2,2,2-trifluoro-N-{2-[1-(3-methyl-pyridin-2-yl)-1H-imidazole-2-sulfinylmethyl]-phenyl}-acetamide 
• 1027589-16-7 2,2,2-Trifluoro-N-{2-[1-(3-methoxy-pyridin-2-yl)-1H-imidazol-2-ylsulfanylmethyl]-phenyl}-acetamide 
• 173472-09-8 2,2,2-Trifluoro-N-methyl-N-{2-[1-(3-methyl-pyridin-2-yl)-1H-imidazole-2-sulfinylmethyl]-phenyl}-acetamide 

Relevant articles and documents

Photodecarboxylative cyclizations of ω-phthalimido-ortho-phenoxy carboxylates

ω-Phthalimido-ortho-phenoxy carboxylates efficiently undergo photodecarboxylative cyclizations in reasonable to good yields of 12-75%. Although the photocyclization efficiency decreases with increasing carbon chain lengths, target ring sizes up to 15 are

Synthesis of imides via palladium-catalyzed three-component coupling of aryl halides, isocyanides and carboxylic acids

A palladium-catalyzed three-component synthesis of acyclic imides from feedstock aryl halides, carboxylic acids and isocyanides through the intermediacy of isoimides has been developed. The key to the success of this approach was controlled isocyanide slow addition and organic/aqueous biphasic conditions. This transition-metal-catalyzed approach features readily available starting materials, atom- and step-economy, good functional group compatibility and gram-scale synthetic capability. Utilization of this new method is illustrated in the late-stage functionalization of drugs Carprofen, Loxoprofen and Flurbiprofen. This strategy has also been successfully applied in the synthesis of cyclic imides including phthalimide, homophthalimide, and 2H-2-benzazepine-1,3-dione derivatives.

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.