4770-74-5

Usage

Uses

Used in Organic Synthesis:
2-(4-nitrophenyl)-2,3-dihydro-1H-isoindol-1-one is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a key component in the synthesis of complex organic molecules, contributing to the development of new materials and chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(4-nitrophenyl)-2,3-dihydro-1H-isoindol-1-one is used as a precursor for the synthesis of pharmaceuticals. Its potential biological activities, such as antimicrobial, antifungal, and anti-inflammatory properties, make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Dye Industry:
2-(4-nitrophenyl)-2,3-dihydro-1H-isoindol-1-one is used as a precursor in the synthesis of dyes. Its chemical properties enable the creation of a wide range of dyes with different colors and properties, which can be used in various applications, such as textiles, plastics, and printing inks.
Used in Polymer Industry:
In the polymer industry, 2-(4-nitrophenyl)-2,3-dihydro-1H-isoindol-1-one is used as a monomer or a building block for the synthesis of polymers. Its versatility allows for the development of polymers with specific properties, such as improved strength, flexibility, or thermal stability, which can be utilized in various applications, including automotive, electronics, and packaging industries.
Used in Research and Development:
2-(4-nitrophenyl)-2,3-dihydro-1H-isoindol-1-one is used as a research compound for exploring its potential applications and properties. Its unique structure and functional groups make it an interesting subject for studying its reactivity, stability, and interactions with other molecules, which can lead to the discovery of new chemical reactions and applications.

Upstream product

• 97166-80-8 2-(4-nitro-phenyl)-isoindolin-1-one-imine 
• 100-01-6 4-nitro-aniline 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 5388-42-1 N-phenylphthalimidine 
• 7664-93-9 sulfuric acid 
• 119-67-5 o-carboxybenzaldehyde 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 2417-73-4 methyl 2-bromomethylbenzoate 

Downstream Products

• 120972-66-9 2-(4-amino-phenyl)-isoindolin-1-one 

Relevant academic research and scientific papers

One-pot method to construct isoindolinones and its application to the synthesis of DWP205109 and intermediate of Lenalidomide

Herein a practical and efficient system for concise synthesis of isoindolinones is described by using substituted methyl 2-(halomethyl)benzoates and substituted amines. Structurally various methyl 2-(halomethyl)benzoates and amines were transformed into isoindolinones 80–99% yield and purity in catalyst-free and solvent-free conditions. The method has a wide substrate scope. The synthetic utility of the one-pot reaction was demonstrated by the concise syntheses of Lenalidomide intermediate and DWP205190.

Synthetic method of isoindolinone compound

The invention belongs to the field of chemical synthesis, and particularly relates to a synthesis method of an isoindolinone compound. The isoindolinone compound is represented by formula (I), in which R, R1 and R2 are used for representing any substituent groups. According to the synthetic method of the isoindolinone compound, a new process for solvent-free synthesis of the isoindolinone compoundis developed; no solvent is used, so that the separation and purification process of the product is easier to carry out, the green production of fine chemicals is effectively realized, the operationis simple, the reaction time is obviously shortened, the production efficiency of the product is increased, the quality and yield are improved, the yield can reach 81%-99%, and the purity can reach 96%-99%.

Application of the mild-condition phthalimidine synthesis with use of 1,2,3-1h-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries. Effective synthesis of phthalimidines possessing a variety of substituents at 2-position

The mild-condition phthalimidine synthesis based on Mannich type 1:1 condensation reaction between o-phthalaldehyde with a variety of primary amines in the presence of excess 2-mercaptoethanol and 1,2,3-1H-benzotriazole as "dual synthetic auxiliaries" in MeCN for 13 h at room temperature afford 2-substituted phthalimidines (2,3-dihydroisoindol-1-one) in fair to good isolated yields.

Lead optimization of the VU0486321 series of mGlu1 PAMs. Part 3. Engineering plasma stability by discovery and optimization of isoindolinone analogs

This Letter describes the further lead optimization of the VU0486321 series of mGlu1 positive allosteric modulators (PAMs), focused on addressing the recurrent issue of plasma instability of the phthalimide moiety. Here, we evaluated a number of phthalimide bioisosteres, and ultimately identified isoindolinones as the ideal replacement that effectively address plasma instability, while maintaining acceptable mGlu1 PAM potency, DMPK profile, CNS penetration and mGluR selectivity.

Synthesis of substituted amines and isoindolinones: Catalytic reductive amination using abundantly available AlCl3/PMHS

AlCl3 has been employed for highly chemoselective reductive amination of carbonyl compounds in ethanol using polymethylhydrosiloxane as an inexpensive, stable and safe reducing agent without an inert atmosphere. A large range of functional groups such as nitro, carboxylic acid, acetyl, nitrile, halogen, methoxy, alkene and heterocycles were well tolerated. AlCl3 also catalyzed tandem amination-amidation of 2-carboxybenzaldehyde with different amines to afford N-substituted isoindolinones. The catalyst can be recycled at least three times without any significant effect on activity and selectivity.

Direct one-pot cobalt(II) phthalocyanine catalyzed synthesis of N-substituted isoindolinones

A direct one-pot synthetic approach is described wherein cobalt(II) phthalocyanine (CoPc) catalyzed reductive amination of 2-carboxybenzaldehyde, followed by intramolecular amidation afforded N-substituted isoindolinones. The method used diphenylsilane as reducing agent in ethanol. High chemoselectivity with excellent yield was obtained in most of the studied substrates.

Preparation of 2-substituted 1,3-bis(benzotriazol-1-yl)isoindolines by the double mannich conden-sation reaction of o-phthalaldehyde with primary amines in the presence of 1,2,3-1 h-benzotriazole

The preparation of isoindolines (1,3-dihydro-2H-isoindoles) possessing two reactive centers as mixed aminals is investigated. In the double Mannich condensation reaction of o-phthalaldehyde with a variety of primary amines in the presence of 1,2,3-1H-benzotriazole (Bt-H) in MeCN, Bt-substituted isoindolines are obtained in fair to good yields when anilines are used as amines.