tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (CAS 1201187-44-1): A Comprehensive Product Introduction
Overview
Tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate, with the CAS number 1201187-44-1, is a significant organic compound in the field of chemistry. This compound has drawn considerable attention from researchers and scientists due to its unique chemical structure and potential applications in various industries. In this article, we will delve into the details of its properties, uses, applications in different fields, and the methods of preparation.
Chemical Properties
The chemical formula of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate is C18H20N4O4S. It is a complex molecule composed of carbon (C), hydrogen (H), nitrogen (N), oxygen (O), and sulfur (S). The molecular weight of this compound is approximately 388.44 g/mol. The presence of the tert-butyl group, tosyl group, and the pyrrolo[2,3-b]pyrazine core structure contributes to its distinct chemical and physical properties.
It is a solid compound under normal conditions. The melting point and boiling point of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate are important physical parameters that can influence its handling and application. Although specific data on these properties may vary depending on the purity and measurement conditions, they play a crucial role in determining the compound’s stability and reactivity.
In terms of solubility, it is likely to have limited solubility in water due to the hydrophobic nature of the organic groups present in the molecule. However, it may show good solubility in organic solvents such as dichloromethane, chloroform, and dimethyl sulfoxide (DMSO). The solubility characteristics are essential for its use in chemical reactions and formulations.
Uses and Applications
Pharmaceutical Industry
In the pharmaceutical industry, tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate holds great potential as a building block for the synthesis of novel drugs. The unique structure of the pyrrolo[2,3-b]pyrazine core can interact with specific biological targets, making it a valuable starting material for the development of drugs with diverse therapeutic activities. For example, it may be used in the design of anti – cancer drugs. Some studies have shown that compounds with similar structures can inhibit the growth of cancer cells by interfering with specific signaling pathways within the cells. By modifying the substituents on the core structure, researchers can optimize the biological activity and selectivity of the resulting drugs.
It can also be used in the development of drugs for neurological disorders. The interaction of the compound with neurotransmitter receptors or enzymes in the nervous system may lead to the discovery of new treatments for diseases such as Alzheimer’s and Parkinson’s. The ability to fine – tune the chemical properties of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate allows for the exploration of different pharmacological mechanisms.
Material Science
In material science, this compound can be incorporated into polymers or materials to enhance their properties. For instance, when added to a polymer matrix, it may improve the mechanical strength, thermal stability, or electrical conductivity of the material. The presence of the sulfur and nitrogen atoms in the molecule can form strong intermolecular interactions, which contribute to the overall performance of the material. In the field of organic electronics, tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate may be used as a semiconductor material. Its unique electronic structure can enable the efficient transport of charge carriers, making it suitable for applications in organic field – effect transistors (OFETs) and organic photovoltaic cells (OPVs). The development of such materials is crucial for the advancement of flexible and printable electronics.
Agrochemical Industry
In the agrochemical industry, tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate may be used in the synthesis of pesticides and herbicides. The compound’s ability to interact with specific biological targets in pests or weeds can be exploited to develop more effective and environmentally friendly agrochemicals. By modifying the chemical structure, it is possible to design compounds with high selectivity, which can target specific pests while minimizing the impact on non – target organisms. Additionally, the stability and solubility of the compound can be optimized to ensure its effectiveness in different agricultural environments.
Preparation Methods
Multi – step Synthesis
The preparation of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate typically involves a multi – step synthesis process. One common approach starts with the synthesis of the pyrrolo[2,3-b]pyrazine core. This can be achieved through a series of cyclization reactions using appropriate starting materials. For example, a condensation reaction between a suitable amine and a carbonyl compound can form the basic ring structure. After the formation of the pyrrolo[2,3-b]pyrazine core, the tosyl group is introduced through a substitution reaction. The tosyl chloride is often used as the tosylating agent in the presence of a base to facilitate the reaction. Finally, the tert – butyl carbamate group is added through a carbamation reaction. This can be carried out using tert – butyl chloroformate in the presence of a catalyst or a base.
The reaction conditions, such as temperature, reaction time, and the choice of solvents and catalysts, need to be carefully controlled to ensure high yields and purity of the final product. Purification steps, such as column chromatography or recrystallization, are often required to obtain the desired compound with the required quality.
Optimization of Synthesis
To improve the efficiency and yield of the synthesis process, researchers have been exploring various optimization strategies. For example, the use of microwave – assisted synthesis can significantly reduce the reaction time and increase the reaction rate. The microwave energy can selectively heat the reaction mixture, leading to more efficient bond formation. Another approach is the use of green chemistry principles, such as the use of environmentally friendly solvents and catalysts. This not only reduces the environmental impact of the synthesis process but also makes the production more sustainable.
Conclusion
Tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate is a compound with significant potential in multiple industries. Its unique chemical structure and properties make it a valuable starting material for the synthesis of drugs, materials, and agrochemicals. The development of efficient preparation methods and the exploration of its applications will continue to be important areas of research in the future. If you are interested in this product, please click the button below to send an inquiry.
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