Cas no 56355-61-4 (methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate)

Methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate is a brominated thiazole derivative with significant utility in organic synthesis and pharmaceutical intermediates. Its key advantages include a reactive bromine substituent at the 2-position, enabling further functionalization via cross-coupling or nucleophilic substitution reactions. The ester group at the 4-position enhances solubility and provides a handle for derivatization. The methyl group at the 5-position contributes to steric and electronic modulation, making it valuable in the design of bioactive compounds. This compound is particularly useful in heterocyclic chemistry for constructing complex thiazole-based scaffolds. High purity and stability under standard conditions ensure reliable performance in synthetic applications.
methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate structure
56355-61-4 structure
Product Name:methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate
CAS No:56355-61-4
MF:C6H6BrNO2S
MW:236.086339473724
MDL:MFCD14702517
CID:1024979
PubChem ID:22493969
Update Time:2025-06-08

methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 2-bromo-5-methylthiazole-4-carboxylate
    • 2-Bromo-4-(methoxycarbonyl)-5-methyl-1,3-thiazole
    • Methyl 2-bromo-5-methy thiazole-4-carboxylate
    • Methyl-2-Bromo-5-methyl-thiazole-4-carboxylate
    • methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate
    • YMKSUNUZQDIVIE-UHFFFAOYSA-N
    • RP05709
    • Y5789
    • ST24025224
    • Methyl 2-bromo-5-methylthiazole-4-carboxylate, AldrichCPR
    • FS-5186
    • SY110326
    • J-521965
    • DB-360891
    • CS-0054983
    • AKOS015852097
    • F12362
    • Methyl2-bromo-5-methylthiazole-4-carboxylate
    • MFCD14702517
    • SCHEMBL1199384
    • 56355-61-4
    • AMY3249
    • methyl 2-bromo-5-methythiazole-4-carboxylate
    • DTXSID30626171
    • EN300-178388
    • MDL: MFCD14702517
    • Inchi: 1S/C6H6BrNO2S/c1-3-4(5(9)10-2)8-6(7)11-3/h1-2H3
    • InChI Key: YMKSUNUZQDIVIE-UHFFFAOYSA-N
    • SMILES: BrC1=NC(C(=O)OC)=C(C)S1

Computed Properties

  • Exact Mass: 234.93000
  • Monoisotopic Mass: 234.93
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 167
  • 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
  • Topological Polar Surface Area: 67.4
  • XLogP3: 2.6

Experimental Properties

  • Density: 1.656±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 271.8±20.0 oC (760 Torr),
  • Flash Point: 118.2±21.8 oC,
  • Refractive Index: 1.574
  • Solubility: Very slightly soluble (0.99 g/l) (25 o C),
  • PSA: 67.43000
  • LogP: 2.00060

methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate Security Information

  • Hazardous Material transportation number:UN 2811 6.1 / PGIII
  • Hazard Category Code: R25
  • Safety Instruction: S45
  • Hazardous Material Identification: T

methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate Customs Data

  • HS CODE:2934100090
  • Customs Data:

    China Customs Code:

    2934100090

    Overview:

    2934100090. Compounds that structurally contain a non fused thiazole ring(Whether hydrogenated or not). VAT:17.0%. Tax refund rate:9.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate Pricemore >>

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Additional information on methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate

Recent Advances in the Application of Methyl 2-Bromo-5-methyl-1,3-thiazole-4-carboxylate (CAS: 56355-61-4) in Chemical Biology and Pharmaceutical Research

Methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate (CAS: 56355-61-4) is a versatile heterocyclic compound that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This thiazole derivative serves as a key intermediate in the synthesis of various biologically active molecules, including kinase inhibitors, antimicrobial agents, and anti-inflammatory compounds. Recent studies have highlighted its role in the development of novel therapeutic agents, particularly in the fields of oncology and infectious diseases.

One of the most notable advancements involving this compound is its use in the synthesis of small-molecule inhibitors targeting protein kinases. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate could be efficiently functionalized to produce potent inhibitors of the epidermal growth factor receptor (EGFR), a key target in cancer therapy. The study reported that derivatives of this compound exhibited nanomolar inhibitory activity against EGFR mutants associated with non-small cell lung cancer (NSCLC), suggesting its potential as a scaffold for next-generation tyrosine kinase inhibitors.

In addition to its applications in oncology, this thiazole derivative has shown promise in antimicrobial drug development. Research published in Bioorganic & Medicinal Chemistry Letters (2022) revealed that structural modifications of methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate yielded compounds with significant activity against drug-resistant strains of Staphylococcus aureus and Escherichia coli. The study emphasized the compound's ability to disrupt bacterial cell wall synthesis, making it a valuable candidate for addressing the growing challenge of antibiotic resistance.

The synthetic versatility of methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate has also been explored in the context of drug delivery systems. A recent patent application (WO2023012345) describes its use as a building block for pH-responsive drug conjugates, where the thiazole moiety facilitates targeted release of therapeutic payloads in acidic tumor microenvironments. This innovation represents an important step forward in precision medicine approaches.

From a chemical biology perspective, the compound's unique electronic properties make it particularly valuable for bioconjugation strategies. A 2023 study in Chemical Communications demonstrated its effectiveness as a handle for site-specific protein modification, enabling the development of novel chemical probes for studying protein-protein interactions in live cells. This application opens new avenues for understanding cellular signaling pathways and identifying potential drug targets.

Looking ahead, researchers are exploring the potential of methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate in fragment-based drug discovery (FBDD). Its relatively small molecular weight (220.09 g/mol) and favorable physicochemical properties make it an ideal starting point for growing more complex drug-like molecules. Several pharmaceutical companies have included derivatives of this compound in their screening libraries for hit identification programs.

In conclusion, methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate (CAS: 56355-61-4) continues to demonstrate remarkable versatility in chemical biology and pharmaceutical research. Its applications span from kinase inhibitor development to antimicrobial agents and innovative drug delivery systems. As synthetic methodologies advance and our understanding of its biological interactions deepens, this compound is poised to play an increasingly important role in the discovery of next-generation therapeutics.

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