Cas no 1000575-16-5 (Methyl 4-Bromo-2-chlorothiazole-5-carboxylate)

Methyl 4-Bromo-2-chlorothiazole-5-carboxylate is a versatile heterocyclic building block widely used in pharmaceutical and agrochemical synthesis. Its reactive bromo and chloro substituents facilitate further functionalization, making it valuable for constructing complex thiazole derivatives. The ester group enhances solubility and provides a handle for subsequent transformations, such as hydrolysis or amidation. This compound is particularly useful in medicinal chemistry for developing bioactive molecules due to the thiazole core's prevalence in drug candidates. High purity and stability under standard storage conditions ensure reliable performance in synthetic applications. Its well-defined reactivity profile allows for selective modifications, supporting efficient route design in multi-step syntheses.
Methyl 4-Bromo-2-chlorothiazole-5-carboxylate structure
1000575-16-5 structure
Product Name:Methyl 4-Bromo-2-chlorothiazole-5-carboxylate
CAS No:1000575-16-5
MF:C5H3BrClNO2S
MW:256.504818201065
CID:3157680
PubChem ID:26598971
Update Time:2025-05-23

Methyl 4-Bromo-2-chlorothiazole-5-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 4-Bromo-2-chlorothiazole-5-carboxylate
    • Methyl4-bromo-2-chlorothiazole-5-carboxylate
    • MFCD09878034
    • G83361
    • 1000575-16-5
    • methyl 4-bromo-2-chloro-1,3-thiazole-5-carboxylate
    • MDL: MFCD09878034
    • Inchi: 1S/C5H3BrClNO2S/c1-10-4(9)2-3(6)8-5(7)11-2/h1H3
    • InChI Key: IIJWBQWNNFDNAV-UHFFFAOYSA-N
    • SMILES: BrC1=C(C(=O)OC)SC(=N1)Cl

Computed Properties

  • Exact Mass: 254.87564g/mol
  • Monoisotopic Mass: 254.87564g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 171
  • 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: 3.1
  • Topological Polar Surface Area: 67.4?2

Methyl 4-Bromo-2-chlorothiazole-5-carboxylate Pricemore >>

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Additional information on Methyl 4-Bromo-2-chlorothiazole-5-carboxylate

Methyl 4-Bromo-2-chlorothiazole-5-carboxylate (CAS No. 1000575-16-5): A Versatile Intermediate in Modern Pharmaceutical Synthesis

Methyl 4-Bromo-2-chlorothiazole-5-carboxylate, identified by its CAS number 1000575-16-5, is a significant compound in the realm of pharmaceutical chemistry. This heterocyclic compound features a thiazole core substituted with bromine and chlorine atoms, making it a valuable intermediate in the synthesis of various biologically active molecules. The strategic placement of these halogen atoms enhances its reactivity, allowing for diverse functionalization and modification, which is crucial for developing novel therapeutic agents.

The thiazole ring itself is a prominent scaffold in medicinal chemistry, known for its broad spectrum of biological activities. Compounds containing thiazole moieties have been extensively studied for their potential applications in treating infections, inflammation, and even cancer. The presence of both bromine and chlorine substituents in Methyl 4-Bromo-2-chlorothiazole-5-carboxylate makes it particularly interesting for further derivatization, as these halogens can participate in various chemical reactions such as cross-coupling, nucleophilic substitution, and metal-catalyzed transformations.

In recent years, there has been a surge in research focused on developing small-molecule inhibitors targeting specific enzymes and pathways involved in disease mechanisms. Methyl 4-Bromo-2-chlorothiazole-5-carboxylate has emerged as a key building block in the synthesis of such inhibitors. For instance, studies have demonstrated its utility in creating potent kinase inhibitors, which are critical in cancer therapy. The brominated thiazole derivative can be further functionalized to produce compounds that selectively inhibit aberrant signaling pathways, thereby offering new therapeutic strategies.

Another area where Methyl 4-Bromo-2-chlorothiazole-5-carboxylate has shown promise is in the development of antimicrobial agents. The increasing prevalence of drug-resistant bacteria has necessitated the discovery of novel antibiotics with unique mechanisms of action. Researchers have leveraged the reactivity of this compound to design molecules that disrupt bacterial cell wall synthesis or interfere with essential metabolic processes. The combination of bromine and chlorine atoms provides multiple sites for chemical manipulation, enabling the creation of structurally diverse antimicrobial compounds.

The compound's versatility also extends to its role in material science and agrochemical applications. Thiazole derivatives are known to exhibit properties that make them suitable for use in dyes, corrosion inhibitors, and pesticides. Methyl 4-Bromo-2-chlorothiazole-5-carboxylate can be modified to produce derivatives with enhanced stability or specific functionalities tailored for these applications. For example, researchers have explored its potential as a precursor for synthesizing advanced materials with applications in electronics and coatings.

Advances in synthetic methodologies have further expanded the utility of Methyl 4-Bromo-2-chlorothiazole-5-carboxylate. Modern techniques such as palladium-catalyzed cross-coupling reactions allow for efficient introduction of various functional groups at specific positions on the thiazole ring. This flexibility has enabled the rapid discovery and optimization of novel compounds with improved pharmacological profiles. Additionally, computational chemistry approaches have been employed to predict the reactivity and biological activity of derivatives derived from this intermediate, streamlining the drug discovery process.

The importance of Methyl 4-Bromo-2-chlorothiazole-5-carboxylate is underscored by its increasing demand in both academic and industrial research settings. Pharmaceutical companies and biotechnology firms rely on this compound as a starting material for synthesizing lead compounds that undergo further testing in preclinical and clinical trials. The ability to rapidly modify its structure allows researchers to explore a wide range of chemical space, increasing the likelihood of identifying potent and selective therapeutic agents.

In conclusion, Methyl 4-Bromo-2-chlorothiazole-5-carboxylate (CAS No. 1000575-16-5) is a multifaceted compound with significant applications across multiple disciplines. Its unique structural features make it an invaluable intermediate for synthesizing biologically active molecules with potential therapeutic benefits. As research continues to uncover new applications and synthetic strategies, this compound is poised to remain a cornerstone in pharmaceutical innovation.

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