Cas no 7520-95-8 (2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone)

2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone is a brominated ketone derivative featuring a substituted thiazole core. This compound is of interest in synthetic organic chemistry due to its reactive α-bromo ketone moiety, which facilitates nucleophilic substitution and cyclization reactions. The presence of the 4-methyl-2-phenyl-1,3-thiazol-5-yl group enhances its utility as a versatile intermediate in the synthesis of heterocyclic compounds, particularly in pharmaceutical and agrochemical research. Its well-defined structure and stability under controlled conditions make it suitable for precise functionalization in complex molecular frameworks. The compound is typically handled under inert conditions to preserve its reactivity and purity.
2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone structure
7520-95-8 structure
Product Name:2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone
CAS No:7520-95-8
MF:C12H10BrNOS
MW:296.182900905609
CID:981583
PubChem ID:2795492
Update Time:2025-10-28

2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)ethanone
    • 2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone
    • 2-bromo-1-(4-methyl-2-phenyl-thiazol-5-yl)-ethanone
    • 2-Phenyl-4-methyl-5-bromacetyl-thiazol
    • 5-bromoacetyl-4-methyl-2-phenylthiazole
    • AKOS022947436
    • SCHEMBL18550684
    • 7520-95-8
    • FT-0730290
    • DTXSID30383712
    • J-508152
    • 2-Bromo-1-(4-methyl-2-phenylthiazol-5-yl)ethanone
    • BOMSILGSXFNLJX-UHFFFAOYSA-N
    • DB-025847
    • Inchi: 1S/C12H10BrNOS/c1-8-11(10(15)7-13)16-12(14-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
    • InChI Key: BOMSILGSXFNLJX-UHFFFAOYSA-N
    • SMILES: BrCC(C1=C(C)N=C(C2C=CC=CC=2)S1)=O

Computed Properties

  • Exact Mass: 294.96700
  • Monoisotopic Mass: 294.96665g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 255
  • 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: 3.8
  • Topological Polar Surface Area: 58.2?2

Experimental Properties

  • Melting Point: 117 °C
  • PSA: 58.20000
  • LogP: 3.69610

2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone Pricemore >>

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B816815-50mg
2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone
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Additional information on 2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone

Introduction to 2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone (CAS No. 7520-95-8) and Its Emerging Applications in Chemical Biology

The compound 2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone (CAS No. 7520-95-8) represents a fascinating molecular scaffold with significant potential in the realm of chemical biology and drug discovery. Its unique structural features, encompassing a brominated ketone moiety linked to a substituted thiazole ring, make it a valuable intermediate for synthesizing bioactive molecules. This introduction delves into the compound's chemical properties, synthetic pathways, and its role in contemporary research, emphasizing its relevance to cutting-edge developments in medicinal chemistry.

The molecular structure of 2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone is characterized by a central carbonyl group (C=O) flanked by a bromine atom and an aromatic thiazole ring system. The thiazole core is further substituted with a methyl group at the 4-position and a phenyl ring at the 2-position, which collectively contribute to its distinct electronic and steric properties. This arrangement not only enhances its solubility in organic solvents but also facilitates interactions with biological targets such as enzymes and receptors.

In recent years, the pharmaceutical industry has witnessed a surge in interest toward heterocyclic compounds due to their diverse biological activities. Among these, thiazole derivatives have emerged as pivotal scaffolds in drug design, owing to their ability to modulate various cellular processes. The presence of the bromine atom in 2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone adds another layer of utility, as bromine can serve as a handle for further functionalization via cross-coupling reactions like Suzuki or Buchwald-Hartwig couplings. These reactions are instrumental in constructing complex molecular architectures essential for developing novel therapeutics.

One of the most compelling aspects of this compound is its application in the synthesis of kinase inhibitors. Kinases are enzymes that play crucial roles in signal transduction pathways and are implicated in numerous diseases, including cancer and inflammatory disorders. The thiazole ring in 2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yll)-1 ethanone can be strategically positioned to interact with the ATP-binding pockets of kinases, while the brominated ketone moiety allows for modifications that enhance binding affinity. Recent studies have demonstrated that derivatives of this compound exhibit potent inhibitory effects on specific kinases, making them promising candidates for further development into drugs.

Furthermore, the compound has shown promise in antimicrobial research. The structural motifs present in 2-Bromo -1-(4-methyl -2 -phenyl -1 ,3 -thiazol -5 -y l)-1 ethanone can disrupt bacterial cell wall synthesis or interfere with essential metabolic pathways. Preliminary experiments have indicated that certain analogs exhibit activity against Gram-positive bacteria, suggesting their potential use in combating antibiotic-resistant strains. This aligns with global efforts to discover new antimicrobial agents due to the growing threat of resistant pathogens.

The synthetic route to 2-Bromo -1-(4-methyl -2 -phenyl -1 ,3 -thiazol -5 -y l)-1 ethanone involves multi-step organic transformations starting from readily available precursors. A common approach begins with the condensation of 4-methylthiophene derivatives with acetyl bromide to form an intermediate thiazole ketone. Subsequent bromination at the desired position followed by coupling reactions introduces the phenyl group and other substituents. The optimization of these synthetic steps is crucial for achieving high yields and purity, which are essential for subsequent biological evaluations.

Advances in computational chemistry have further enhanced the utility of 2-Bromo -1-(4-methyl -2 -phenyl -1 ,3 -thiazol -5 yl)- 1 ethanone by enabling virtual screening of its derivatives for specific biological targets. Molecular docking studies have been employed to predict binding modes and affinities, allowing researchers to design more effective analogs with minimal experimental trials. This integration of computational methods with traditional synthetic chemistry has accelerated the discovery pipeline for novel bioactive molecules.

The safety profile of CAS No 7520 95 8 is another critical consideration during its development and application. While preliminary toxicology studies suggest that it exhibits moderate solubility and stability under standard conditions, further comprehensive assessments are necessary before considering its use in clinical settings. These studies will evaluate its potential side effects, metabolic pathways, and environmental impact to ensure safe handling and disposal.

In conclusion,CAS No 7520 95 8 stands out as a versatile building block in pharmaceutical research due to its unique structural features and functionalization potential. Its role in developing kinase inhibitors and antimicrobial agents underscores its importance in addressing critical unmet medical needs. As research progresses,CAS No 7520 95 8and its derivatives will continue to be explored for their therapeutic applications,contributing significantly to advancements in chemical biology and drug discovery.

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