Production Method 1

219611-74-2

1875-48-5

90564-77-5

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ,  Water ;  rt; 5 h, reflux; overnight, 4 °C

Reference

Synthesis and cytotoxic activity of (4-substituted-benzylidene)-(3-phenyl-1,2,4-oxadiazol-5-yl)methylamines

Kucukoglu, K.; Tugrak, M.; Demirtas, A.; Sakagami, H.; Gul, H. I., Pharmaceutical Chemistry Journal, 2016, 50(4), 234-238

2-Aminoisoindoline-1,3-dione Raw materials

• 2-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione

2-Aminoisoindoline-1,3-dione Preparation Products

• (3-Phenyl-1,2,4-oxadiazol-5-yl)methanamine (90564-77-5)
• 2-Aminoisoindoline-1,3-dione (1875-48-5)

• 1. Microwave assisted synthesis of five membered nitrogen heterocycles
  Gopinadh Meera,K. R. Rohit,Salim Saranya,Gopinathan Anilkumar RSC Adv. 2020 10 36031
• 2. A solvent controlled three-component reaction of diazo compounds for the synthesis of hydrazone compounds under Br?nsted acid catalysis
  Hangli He,Zhewei Yan,Junyong Wang,Qiongjiao Yan,Wei Wang,Haifeng Wang,Fener Chen New J. Chem. 2022 46 22513
• 3. 4. Chemiluminescent organic compounds. Part I. Isomeric simple and complex hydrazides of phthalic acid and mode of formation of phthalazine and isoindole rings
  H. D. K. Drew,H. H. Hatt J. Chem. Soc. 1937 16
• 4. Synthesis of N-(protected)aminophthalimides: application to the synthesis of singly labelled isoniazid
  Nicolas Brosse,Maria-Fatima Pinto,Brigitte Jamart-Grégoire J. Chem. Soc. Perkin Trans. 1 1998 3685
• 5. A review on the sustainable routes for the synthesis and applications of cuprous oxide nanoparticles and their nanocomposites
  Sushma Yadav,Arti Jain,Priti Malhotra Green Chem. 2019 21 937

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoindoles and derivatives Isoindolones
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoindoles and derivatives Isoindolines Isoindolones

2-Aminoisoindoline-1,3-dione (CAS No. 1875-48-5): A Versatile Building Block in Organic Synthesis and Pharmaceutical Research

2-Aminoisoindoline-1,3-dione (CAS No. 1875-48-5), also known as 2-amino-1H-isoindole-1,3(2H)-dione, is a highly valuable heterocyclic compound that has gained significant attention in recent years due to its versatile applications in organic synthesis, medicinal chemistry, and material science. This compound belongs to the class of isoindoline derivatives, which are known for their unique structural features and diverse biological activities.

The molecular structure of 2-Aminoisoindoline-1,3-dione consists of a fused bicyclic system containing a five-membered nitrogen-containing ring (pyrrole) and a six-membered ring with two carbonyl groups. This distinctive isoindole-1,3-dione scaffold imparts interesting chemical properties that make it an attractive building block for the synthesis of more complex molecules. Researchers have been particularly interested in exploring its potential as a precursor for pharmaceutical intermediates and functional materials.

In the pharmaceutical field, 2-Aminoisoindoline-1,3-dione derivatives have shown promising biological activities. Recent studies published in journals like the Journal of Medicinal Chemistry highlight their potential as kinase inhibitors and antimicrobial agents. The compound's ability to serve as a hydrogen bond acceptor and donor makes it particularly valuable in drug design, where molecular interactions play a crucial role in biological activity. This has led to increased interest from researchers working on targeted drug delivery systems and small molecule therapeutics.

The synthesis of 2-Aminoisoindoline-1,3-dione typically involves the reaction of phthalic anhydride derivatives with hydrazine or its derivatives. Modern synthetic approaches focus on developing more efficient and environmentally friendly methods, reflecting the growing demand for green chemistry solutions in organic synthesis. Recent patents have disclosed improved synthetic routes that offer better yields and reduced environmental impact, addressing one of the most searched topics in chemical synthesis today.

Beyond pharmaceutical applications, 2-Aminoisoindoline-1,3-dione has found use in materials science. Its rigid, planar structure and electron-deficient character make it suitable for developing organic electronic materials, particularly in the field of organic light-emitting diodes (OLEDs) and organic photovoltaics. Researchers are exploring its potential as an electron-transporting material, capitalizing on the current industry focus on sustainable energy solutions and advanced display technologies.

The compound's stability under various conditions has made it a subject of interest in analytical chemistry as well. It serves as a useful standard or reference compound in chromatographic methods and mass spectrometry studies. This application aligns with the increasing need for reliable analytical standards in quality control laboratories worldwide.

Market trends indicate growing demand for 2-Aminoisoindoline-1,3-dione and its derivatives, particularly from the pharmaceutical and specialty chemicals sectors. According to recent market reports, the compound's versatility and the expanding applications of isoindoline-based compounds are driving this growth. Suppliers are responding by developing more efficient production processes and offering the compound in various purity grades to meet different industry requirements.

Quality control is paramount when working with 2-Aminoisoindoline-1,3-dione. Reputable suppliers provide comprehensive analytical data including HPLC chromatograms, NMR spectra, and mass spectrometry results to ensure product consistency. This attention to quality reflects the broader industry trend toward stringent quality standards in fine chemicals, a topic frequently searched by procurement specialists and researchers alike.

Storage and handling of 2-Aminoisoindoline-1,3-dione require standard laboratory precautions. The compound should be stored in a cool, dry place, protected from light and moisture. These storage conditions are typical for many nitrogen-containing heterocycles and follow established best practices for handling organic compounds in research and industrial settings.

Recent scientific literature reveals ongoing research into novel derivatives of 2-Aminoisoindoline-1,3-dione, particularly focusing on structure-activity relationships. This aligns with current trends in fragment-based drug discovery and computational chemistry, where small, well-characterized molecular fragments serve as starting points for drug development. The compound's relatively simple yet functionalizable structure makes it ideal for such approaches.

Environmental considerations are increasingly important in chemical research and development. While 2-Aminoisoindoline-1,3-dione itself doesn't present significant environmental concerns, researchers are investigating its biodegradation pathways and potential ecological impacts as part of comprehensive environmental risk assessments. This reflects the growing emphasis on green chemistry principles throughout the chemical industry.

In conclusion, 2-Aminoisoindoline-1,3-dione (CAS No. 1875-48-5) represents a versatile and valuable compound with wide-ranging applications in pharmaceutical research, materials science, and organic synthesis. Its unique structural features and multiple reactive sites make it an important building block for developing new drugs, functional materials, and specialty chemicals. As research continues to uncover new applications for this and related isoindoline derivatives, its importance in both academic and industrial settings is likely to grow further.

• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)