Cas no 2227912-04-9 ((1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol)

(1S)-2-Amino-1-(3-bromopyridin-4-yl)ethan-1-ol is a chiral amino alcohol derivative featuring a 3-bromopyridin-4-yl substituent. This compound serves as a valuable intermediate in organic synthesis, particularly in the preparation of pharmaceuticals and bioactive molecules. The presence of both amino and hydroxyl functional groups enables versatile reactivity, facilitating applications in asymmetric synthesis and ligand design. The bromine substituent enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, allowing further structural diversification. Its stereospecific (1S) configuration makes it suitable for enantioselective transformations. The compound is typically handled under controlled conditions due to its sensitivity. High purity grades are available for research and industrial use.
(1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol structure
2227912-04-9 structure
Product Name:(1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol
CAS No:2227912-04-9
MF:C7H9BrN2O
MW:217.063160657883
CID:5846490
PubChem ID:165645657
Update Time:2025-06-13

(1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol Chemical and Physical Properties

Names and Identifiers

    • (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol
    • EN300-1906279
    • 2227912-04-9
    • Inchi: 1S/C7H9BrN2O/c8-6-4-10-2-1-5(6)7(11)3-9/h1-2,4,7,11H,3,9H2/t7-/m1/s1
    • InChI Key: IBXPOYQVFDDCHJ-SSDOTTSWSA-N
    • SMILES: BrC1C=NC=CC=1[C@@H](CN)O

Computed Properties

  • Exact Mass: 215.98983g/mol
  • Monoisotopic Mass: 215.98983g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 123
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.2
  • Topological Polar Surface Area: 59.1?2

(1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol Pricemore >>

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Additional information on (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol

Recent Advances in the Study of (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol (CAS: 2227912-04-9)

The compound (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol (CAS: 2227912-04-9) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential applications in drug discovery and development. This chiral amino alcohol derivative, characterized by its 3-bromopyridin-4-yl moiety, serves as a versatile intermediate in the synthesis of biologically active molecules. Recent studies have explored its utility in the design of kinase inhibitors, antimicrobial agents, and other therapeutic compounds, highlighting its importance in modern pharmaceutical research.

One of the key areas of investigation involves the role of (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol in the development of kinase inhibitors. Kinases are critical targets in oncology and inflammatory diseases, and the bromopyridine scaffold has been shown to enhance binding affinity and selectivity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent inhibitory activity against specific tyrosine kinases, with promising results in preclinical models of cancer. The study also highlighted the compound's favorable pharmacokinetic properties, such as metabolic stability and oral bioavailability.

In addition to its applications in kinase inhibition, (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol has been investigated for its antimicrobial potential. Researchers have synthesized a series of analogs incorporating this scaffold and evaluated their efficacy against drug-resistant bacterial strains. A recent report in Bioorganic & Medicinal Chemistry Letters revealed that certain derivatives exhibit broad-spectrum activity against Gram-positive pathogens, including methicillin-resistant Staphylococcus aureus (MRSA). The presence of the bromine atom was found to be crucial for enhancing membrane penetration and disrupting bacterial cell wall synthesis.

The synthetic accessibility of (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol has also been a focus of recent research. Advances in asymmetric synthesis and catalytic methods have enabled the efficient production of this compound in high enantiomeric purity. A 2024 study in Organic Process Research & Development described a scalable route using chiral auxiliaries and transition metal catalysis, achieving yields exceeding 80% with minimal byproducts. This progress is expected to facilitate the large-scale production of the compound for further pharmacological evaluation.

Despite these promising developments, challenges remain in optimizing the therapeutic potential of (1S)-2-amino-1-(3-bromopyridin-4-yl)ethan-1-ol. Issues such as off-target effects and toxicity profiles need to be addressed through structural modifications and detailed preclinical studies. Future research directions may include the exploration of prodrug strategies and combination therapies to enhance efficacy and reduce adverse effects. Overall, the continued investigation of this compound holds significant promise for advancing drug discovery in multiple therapeutic areas.

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