Cas no 1023814-02-9 (5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile)

5-Bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile is a versatile heterocyclic compound featuring a pyrimidine core functionalized with bromo, methylsulfonyl, and cyano groups. Its structural properties make it a valuable intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The bromo substituent enhances reactivity for cross-coupling reactions, while the methylsulfonyl group contributes to electron-withdrawing effects, facilitating nucleophilic substitutions. The cyano group further expands its utility as a precursor for carboxylic acids, amides, and other derivatives. This compound is well-suited for constructing complex molecular frameworks due to its stability and selective reactivity. Its high purity and well-defined structure ensure reproducibility in research and industrial processes.
5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile structure
1023814-02-9 structure
Product Name:5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile
CAS No:1023814-02-9
MF:C6H4BrN3O2S
MW:262.08385848999
CID:5230061
Update Time:2025-11-01

5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile
    • Inchi: 1S/C6H4BrN3O2S/c1-13(11,12)6-9-3-4(7)5(2-8)10-6/h3H,1H3
    • InChI Key: MMFDKYSVUXQWJB-UHFFFAOYSA-N
    • SMILES: C1(S(C)(=O)=O)=NC=C(Br)C(C#N)=N1

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Additional information on 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile

Introduction to 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile (CAS No. 1023814-02-9)

5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile, with the CAS number 1023814-02-9, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound belongs to the pyrimidine class, which is well-known for its diverse biological activities and applications in drug development. The presence of both bromine and a methylsulfonyl group in its structure imparts unique reactivity, making it a valuable intermediate in synthetic chemistry.

The structural features of 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile make it a versatile building block for the synthesis of more complex molecules. The bromine atom at the 5-position provides a handle for further functionalization via cross-coupling reactions, while the methylsulfonyl group at the 2-position enhances its solubility and reactivity in various chemical transformations. These properties have positioned this compound as a key intermediate in the development of novel therapeutic agents.

In recent years, there has been a surge in research focused on developing new methodologies for the synthesis of heterocyclic compounds, particularly pyrimidines. The demand for efficient and scalable synthetic routes has led to the exploration of novel reagents and catalysts. 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile has emerged as a critical component in several synthetic strategies due to its ability to undergo multiple transformations while maintaining structural integrity.

One of the most notable applications of 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile is in the synthesis of biologically active pyrimidine derivatives. These derivatives have shown promise in various therapeutic areas, including oncology, antiviral, and anti-inflammatory treatments. The compound's ability to serve as a precursor for these derivatives is largely attributed to its reactive sites, which can be selectively modified to introduce additional functional groups.

The pharmaceutical industry has been particularly interested in leveraging the reactivity of 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile to develop new drug candidates. For instance, researchers have utilized this compound to synthesize pyrimidine-based kinase inhibitors, which are known for their effectiveness in targeting specific cancer pathways. The bromine moiety allows for palladium-catalyzed cross-coupling reactions, enabling the introduction of aryl or heteroaryl groups at various positions within the pyrimidine core.

The role of methylsulfonyl groups in enhancing the pharmacological properties of pyrimidine derivatives cannot be overstated. These groups not only improve solubility but also contribute to metabolic stability, making them ideal for drug development. The incorporation of such functionalities has been shown to enhance binding affinity and selectivity, thereby improving overall therapeutic efficacy.

In addition to its pharmaceutical applications, 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile has found utility in agrochemical research. Pyrimidine-based compounds are widely used as herbicides and fungicides due to their ability to disrupt essential biological processes in pests and weeds. The structural versatility of this compound allows researchers to design derivatives with enhanced activity against resistant strains, ensuring sustainable agricultural practices.

The synthesis of 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile typically involves multi-step organic reactions that require careful optimization to ensure high yields and purity. Recent advancements in synthetic methodologies have enabled more efficient production processes, reducing costs and environmental impact. These improvements are crucial for meeting the growing demand for high-quality intermediates in industrial applications.

The use of computational tools and high-throughput screening has further accelerated the discovery and development of novel pyrimidine derivatives derived from 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile. These approaches allow researchers to rapidly evaluate the potential biological activity of different derivatives, facilitating the identification of lead compounds for further optimization.

In conclusion, 5-bromo-2-(methylsulfonyl)pyrimidine-4-carbonitrile (CAS No. 1023814-02-9) is a highly valuable intermediate with broad applications in pharmaceutical and agrochemical research. Its unique structural features enable diverse synthetic transformations, making it an indispensable tool for chemists developing new therapeutic agents and crop protection products. As research continues to evolve, this compound is expected to play an even greater role in advancing drug discovery and sustainable agriculture.

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