Cas no 454483-81-9 (2-(Bromomethyl)thiazole-4-carbonitrile)

2-(Bromomethyl)thiazole-4-carbonitrile is a versatile heterocyclic building block widely used in organic synthesis and pharmaceutical research. This compound features a reactive bromomethyl group and a nitrile functionality, making it valuable for nucleophilic substitution reactions and further derivatization. Its thiazole core is particularly significant in medicinal chemistry, serving as a key scaffold for bioactive molecules. The product is characterized by high purity and stability, ensuring reliable performance in cross-coupling, cyclization, and other synthetic transformations. Its structural features enable efficient incorporation into complex molecular architectures, facilitating the development of agrochemicals, pharmaceuticals, and functional materials. Proper handling under inert conditions is recommended due to its sensitivity to moisture and light.
2-(Bromomethyl)thiazole-4-carbonitrile structure
454483-81-9 structure
Product Name:2-(Bromomethyl)thiazole-4-carbonitrile
CAS No:454483-81-9
MF:C5H3BrN2S
MW:203.059718370438
MDL:MFCD24459268
CID:2139862
PubChem ID:22032729
Update Time:2025-06-09

2-(Bromomethyl)thiazole-4-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 2-(bromomethyl)-1,3-thiazole-4-carbonitrile
    • 830-359-6
    • 2-Bromomethylthiazole-4-carbonitrile
    • 4-Thiazolecarbonitrile, 2-(bromomethyl)-
    • 2-Bromomethyl-thiazole-4-carbonitrile
    • AT15234
    • 2-(BROMOMETHYL)THIAZOLE-4-CARBONITRILE
    • BVHJWNRMSBGEKD-UHFFFAOYSA-N
    • ETA48381
    • DB-312795
    • SCHEMBL1523235
    • EN300-255767
    • 454483-81-9
    • 2-(Bromomethyl)thiazole-4-carbonitrile
    • MDL: MFCD24459268
    • Inchi: 1S/C5H3BrN2S/c6-1-5-8-4(2-7)3-9-5/h3H,1H2
    • InChI Key: BVHJWNRMSBGEKD-UHFFFAOYSA-N
    • SMILES: BrCC1=NC(C#N)=CS1

Computed Properties

  • Exact Mass: 201.92003g/mol
  • Monoisotopic Mass: 201.92003g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 141
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.6
  • Topological Polar Surface Area: 64.9?2

2-(Bromomethyl)thiazole-4-carbonitrile Pricemore >>

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Additional information on 2-(Bromomethyl)thiazole-4-carbonitrile

Professional Introduction to 2-(Bromomethyl)thiazole-4-carbonitrile (CAS No. 454483-81-9)

2-(Bromomethyl)thiazole-4-carbonitrile (CAS No. 454483-81-9) is a versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound, characterized by its bromomethyl and nitrile functional groups, serves as a crucial intermediate in the synthesis of various biologically active molecules. Its unique structural features make it particularly valuable for the development of novel therapeutic agents targeting a range of diseases.

The Bromomethyl moiety in 2-(Bromomethyl)thiazole-4-carbonitrile is highly reactive, allowing for facile functionalization through nucleophilic substitution reactions. This reactivity is exploited in synthetic chemistry to introduce diverse substituents, enabling the creation of complex molecular architectures. The thiazole core is a well-known pharmacophore found in numerous drugs, including those used to treat infections, inflammation, and even cancer. The presence of the nitrile group further enhances its synthetic utility, providing a handle for further derivatization via reduction or hydrolysis.

In recent years, there has been a surge in research focused on developing new thiazole derivatives with enhanced pharmacological properties. Studies have demonstrated that modifications at the 4-position of the thiazole ring can significantly alter the biological activity of compounds. For instance, derivatives with electron-withdrawing groups at this position often exhibit stronger antimicrobial and anti-inflammatory effects. The compound 2-(Bromomethyl)thiazole-4-carbonitrile is particularly interesting because it allows for the introduction of such groups while maintaining high reactivity.

The pharmaceutical industry has shown keen interest in leveraging this compound for drug discovery. Researchers have utilized it as a building block in the synthesis of novel antibiotics, antivirals, and anticancer agents. For example, recent studies have explored its use in generating thiazole-based inhibitors of bacterial enzymes involved in DNA replication and transcription. These inhibitors show promise in preclinical trials for their ability to disrupt pathogenic processes without harming host cells.

Beyond its applications in drug development, 2-(Bromomethyl)thiazole-4-carbonitrile has found utility in materials science and agrochemical research. Its ability to undergo selective functionalization makes it a valuable precursor for synthesizing advanced materials with tailored properties. Additionally, researchers are exploring its potential as a precursor for agrochemicals that offer improved crop protection while minimizing environmental impact.

The synthesis of 2-(Bromomethyl)thiazole-4-carbonitrile typically involves multi-step organic transformations starting from readily available thiazole precursors. The bromomethylation step is critical and requires careful optimization to ensure high yield and purity. Advances in synthetic methodologies have enabled more efficient and scalable production processes, making this compound more accessible for industrial applications.

Ongoing research continues to uncover new applications and derivatives of 2-(Bromomethyl)thiazole-4-carbonitrile. Innovations in computational chemistry and high-throughput screening are accelerating the discovery of novel compounds with enhanced therapeutic potential. Collaborative efforts between academia and industry are essential to translate these findings into tangible benefits for patients worldwide.

In conclusion, 2-(Bromomethyl)thiazole-4-carbonitrile (CAS No. 454483-81-9) is a multifaceted compound with significant implications in pharmaceuticals, materials science, and agrochemicals. Its unique structural features and reactivity make it an indispensable tool for synthetic chemists and researchers striving to develop innovative solutions to global challenges. As our understanding of its properties continues to grow, so too will its role in advancing scientific discovery and improving human health.

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