Cas no 864169-36-8 (2-bromo-5,6-dimethoxy-1,3-benzothiazole)

2-Bromo-5,6-dimethoxy-1,3-benzothiazole is a brominated benzothiazole derivative featuring dimethoxy substituents at the 5 and 6 positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and functional materials. The bromine atom at the 2-position enhances reactivity for cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling efficient derivatization. The dimethoxy groups contribute to electronic modulation, influencing the compound's solubility and binding properties. Its well-defined structure and stability under standard conditions make it a reliable building block for constructing complex heterocyclic frameworks. Suitable for research and industrial applications, it offers consistent performance in synthetic workflows.
2-bromo-5,6-dimethoxy-1,3-benzothiazole structure
864169-36-8 structure
Product Name:2-bromo-5,6-dimethoxy-1,3-benzothiazole
CAS No:864169-36-8
MF:C9H8BrNO2S
MW:274.134320259094
MDL:MFCD11216966
CID:867181
PubChem ID:86069026
Update Time:2025-10-31

2-bromo-5,6-dimethoxy-1,3-benzothiazole Chemical and Physical Properties

Names and Identifiers

    • 2-BROMO-5,6-DIMETHOXYBENZOTHIAZOLE
    • 2-bromo-5,6-dimethoxy-1,3-benzothiazole
    • SCHEMBL19783421
    • 2-Bromo-5,6-dimethoxybenzo[d]thiazole
    • EN300-3539882
    • 864169-36-8
    • MDL: MFCD11216966
    • Inchi: 1S/C9H8BrNO2S/c1-12-6-3-5-8(4-7(6)13-2)14-9(10)11-5/h3-4H,1-2H3
    • InChI Key: MTGQYPIUTNSWAD-UHFFFAOYSA-N
    • SMILES: BrC1=NC2C=C(C(=CC=2S1)OC)OC

Computed Properties

  • Exact Mass: 272.946
  • Monoisotopic Mass: 272.946
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 207
  • 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: 59.6A^2
  • XLogP3: 3.3

2-bromo-5,6-dimethoxy-1,3-benzothiazole Pricemore >>

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Additional information on 2-bromo-5,6-dimethoxy-1,3-benzothiazole

Introduction to 2-bromo-5,6-dimethoxy-1,3-benzothiazole (CAS No. 864169-36-8)

2-bromo-5,6-dimethoxy-1,3-benzothiazole, identified by the Chemical Abstracts Service Number (CAS No.) 864169-36-8, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the benzothiazole class, a scaffold widely recognized for its biological activity and versatility in drug design. The presence of bromine and methoxy substituents on the benzothiazole ring enhances its chemical reactivity, making it a valuable intermediate in synthetic chemistry and a potential candidate for further pharmacological exploration.

The structural features of 2-bromo-5,6-dimethoxy-1,3-benzothiazole make it an intriguing molecule for researchers studying novel therapeutic agents. The benzothiazole core is a fused system consisting of a benzene ring and a thiazole ring, which is known to exhibit various biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The specific substitution pattern, with bromine at the 2-position and methoxy groups at the 5- and 6-positions, contributes to the unique electronic and steric properties of the molecule.

In recent years, there has been a surge in interest regarding heterocyclic compounds as pharmacophores due to their diverse biological activities and favorable pharmacokinetic profiles. 2-bromo-5,6-dimethoxy-1,3-benzothiazole has been explored in several preclinical studies as a potential lead compound for developing new drugs. Its brominated structure allows for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, which are commonly employed in drug discovery to introduce additional functional groups and improve bioavailability.

One of the most compelling aspects of 2-bromo-5,6-dimethoxy-1,3-benzothiazole is its potential application in targeting specific biological pathways. For instance, studies have suggested that benzothiazole derivatives can interact with enzymes and receptors involved in cancer progression. The bromine atom at the 2-position serves as a handle for palladium-catalyzed reactions, enabling the introduction of diverse substituents that may enhance binding affinity to biological targets. This flexibility makes it an attractive scaffold for structure-activity relationship (SAR) studies aimed at optimizing drug candidates.

Moreover, the methoxy groups at the 5- and 6-positions contribute to the lipophilicity of the molecule, which is a critical factor in drug absorption and distribution. By modulating these substituents, researchers can fine-tune the pharmacokinetic properties of 2-bromo-5,6-dimethoxy-1,3-benzothiazole to improve its suitability for therapeutic applications. This balance between hydrophobicity and hydrophilicity is essential for achieving optimal drug delivery and efficacy.

The synthesis of 2-bromo-5,6-dimethoxy-1,3-benzothiazole involves multi-step organic transformations that highlight its synthetic utility. The starting materials typically include commercially available precursors such as 2-aminothiophene-3-carboxylic acid derivatives or halogenated benzothiazoles. Through sequential bromination and methylation reactions under controlled conditions, high yields of the target compound can be obtained. These synthetic routes are well-documented in organic chemistry literature and provide a solid foundation for further modifications.

In academic research circles, 2-bromo-5,6-dimethoxy-1,3-benzothiazole has been employed as a building block in designing novel inhibitors targeting enzyme cascades involved in inflammatory diseases. For example, recent studies have demonstrated its potential as an antagonist of certain proteases implicated in chronic inflammation. By binding to these enzymes with high specificity, 2-bromo-5,6-dimethoxy-1,3-benzothiazole derivatives may offer therapeutic benefits comparable to existing anti-inflammatory drugs but with improved selectivity or reduced side effects.

The pharmaceutical industry has also shown interest in this compound due to its structural similarity to known bioactive molecules. Companies engaged in drug discovery often screen libraries of heterocyclic compounds for their ability to modulate biological pathways relevant to human health. 2-bromo-5,6-dimethoxy-1,3-benzothiazole fits well within this framework as it combines structural features that are both synthetically accessible and biologically relevant.

From a chemical biology perspective, understanding how 2-bromo-5,6-dimethoxy-1,3-benzothiazole interacts with biological targets is crucial for developing effective therapeutics. Computational modeling techniques have been increasingly used to predict binding affinities and optimize molecular interactions. These tools help researchers design derivatives with enhanced potency or selectivity by analyzing molecular docking simulations and predicting binding modes.

The environmental impact of synthesizing and using 2-bromo-5,6-dimethoxy-1,3-benzothiazole is another consideration that merits attention. While halogenated aromatic compounds are valuable intermediates in drug synthesis due to their reactivity and stability under various reaction conditions, their environmental fate must be carefully evaluated. Sustainable synthetic methodologies are being explored to minimize waste generation and reduce hazardous byproducts during production.

In conclusion,2-bromo-5,6-dimethoxy-1,3-benzothiazole (CAS No.864169-36-8) represents a promising compound with significant potential in pharmaceutical research. Its unique structural features enable diverse functionalization strategies while offering opportunities for targeting key biological pathways associated with various diseases. As research continues into novel heterocyclic scaffolds,2-bromo-<5,6-dimethoxy-<1,3-benzote) will likely play an important role in shaping future therapeutic developments.

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