Cas no 67029-82-7 (2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone)

2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone is a brominated aromatic ketone derivative featuring a hydroxyl-substituted naphthalene core. This compound is primarily utilized as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its reactive α-bromo ketone moiety enables efficient participation in nucleophilic substitution and cross-coupling reactions, facilitating the construction of complex molecular frameworks. The hydroxyl group enhances solubility in polar solvents and provides a handle for further functionalization. The compound’s well-defined reactivity profile and stability under controlled conditions make it a valuable reagent for researchers in medicinal chemistry and material science applications. Proper handling is advised due to its potential lachrymatory and irritant properties.
2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone structure
67029-82-7 structure
Product Name:2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone
CAS No:67029-82-7
MF:C12H9BrO2
MW:265.102662801743
MDL:MFCD09745923
CID:395447
PubChem ID:46708451
Update Time:2025-06-14

2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone
    • 2-bromo-1-(1-hydroxy-2-naphthalenyl)Ethanone
    • Ethanone, 2-bromo-1-(1-hydroxy-2-naphthalenyl)-
    • 2-Brom-1-(1-hydroxy-[2]naphthyl)-aethanon
    • 2-bromo-1-(1-hydroxy-[2]naphthyl)-ethanone
    • AK-68329
    • ANW-45394
    • BR-68329
    • CTK1J3987
    • KB-228527
    • W7768
    • 2-bromo-1-(1-hydroxynaphthalen-2-yl)ethan-1-one
    • 67029-82-7
    • AS-66260
    • 2-Bromo-1-(1-hydroxynaphthalene-2-yl)ethanone
    • DTXSID50673743
    • CS-0060582
    • AKOS015919592
    • DB-364639
    • MDL: MFCD09745923
    • Inchi: 1S/C12H9BrO2/c13-7-11(14)10-6-5-8-3-1-2-4-9(8)12(10)15/h1-6,15H,7H2
    • InChI Key: ADLPBUIQLXKAAC-UHFFFAOYSA-N
    • SMILES: BrCC(C1=CC=C2C=CC=CC2=C1O)=O

Computed Properties

  • Exact Mass: 263.97857
  • Monoisotopic Mass: 263.97859g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 242
  • 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: 37.3?2

Experimental Properties

  • PSA: 37.3

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Additional information on 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone

Recent Advances in the Study of 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone (CAS: 67029-82-7) in Chemical Biology and Pharmaceutical Research

The compound 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone (CAS: 67029-82-7) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications as a synthetic intermediate and potential biological activity. This research briefing aims to provide a comprehensive overview of the latest findings related to this compound, focusing on its synthesis, mechanistic insights, and therapeutic potential.

Recent studies have highlighted the role of 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone as a key precursor in the synthesis of naphthoquinone derivatives, which are known for their broad-spectrum biological activities, including antimicrobial, anticancer, and anti-inflammatory properties. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in the efficient synthesis of novel naphthoquinone-based inhibitors targeting tyrosine kinases, which are implicated in various cancers. The study reported a yield optimization strategy that improved the scalability of the synthesis process, making it more feasible for industrial applications.

In addition to its synthetic utility, mechanistic investigations have revealed that 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone exhibits promising bioactivity. Research published in Bioorganic & Medicinal Chemistry Letters (2024) identified its potential as a modulator of reactive oxygen species (ROS) in cellular models. The compound was shown to selectively induce oxidative stress in cancer cells, leading to apoptosis, while sparing normal cells. This selectivity underscores its potential as a lead compound for developing targeted anticancer therapies.

Further exploration of its pharmacological properties has been facilitated by advances in computational chemistry. Molecular docking studies, as reported in a 2024 paper in RSC Advances, have elucidated the binding interactions of 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone with key enzymatic targets, such as cytochrome P450 enzymes. These insights are critical for rational drug design and could pave the way for the development of derivatives with enhanced efficacy and reduced off-target effects.

Despite these promising developments, challenges remain in optimizing the pharmacokinetic profile of 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone. Recent pharmacokinetic studies, such as those presented in the European Journal of Pharmaceutical Sciences (2023), have highlighted issues related to its metabolic stability and bioavailability. Researchers are now focusing on structural modifications, such as the introduction of fluorine atoms or prodrug strategies, to address these limitations.

In conclusion, 2-Bromo-1-(1-hydroxynaphthalen-2-yl)ethanone (CAS: 67029-82-7) represents a compound of high interest in chemical biology and drug discovery. Its dual role as a synthetic building block and a bioactive molecule positions it as a valuable candidate for further research. Future studies should prioritize translational applications, including preclinical evaluation and formulation development, to fully realize its therapeutic potential.

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