Cas no 1391423-76-9 ((R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride)

(R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride is a chiral organic compound featuring a brominated pyridine core and an ethanamine moiety, with the (R)-enantiomeric configuration. This high-purity intermediate is particularly valuable in pharmaceutical synthesis and asymmetric catalysis due to its stereospecificity and reactivity. The bromine substituent enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, while the dihydrochloride salt form improves stability and solubility for handling. Its well-defined chiral center makes it suitable for constructing enantiomerically pure bioactive molecules. The compound is typically used under controlled conditions, with rigorous quality standards to ensure consistency in research and industrial applications.
(R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride structure
1391423-76-9 structure
Product Name:(R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride
CAS No:1391423-76-9
MF:C7H11BrCl2N2
MW:273.985638856888
MDL:MFCD18711638
CID:3042396
PubChem ID:127264634
Update Time:2025-06-13

(R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride Chemical and Physical Properties

Names and Identifiers

    • (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride
    • (1R)-1-(2-bromopyridin-4-yl)ethanamine;dihydrochloride
    • Y10857
    • (R)-1-(2-BROMOPYRIDIN-4-YL)ETHANAMINE 2HCL
    • (R)-2-Bromo-4-(1-amino)-ethylpyridine dihydrochloride
    • MFCD18711638
    • DS-19792
    • CS-0196739
    • (R)-1-(2-Bromopyridin-4-yl)ethanaminedihydrochloride
    • 1391423-76-9
    • AKOS030632957
    • (1R)-1-(2-bromopyridin-4-yl)ethan-1-amine dihydrochloride
    • (1R)-1-(2-BROMOPYRIDIN-4-YL)ETHANAMINE DIHYDROCHLORIDE
    • MDL: MFCD18711638
    • Inchi: 1S/C7H9BrN2.2ClH/c1-5(9)6-2-3-10-7(8)4-6;;/h2-5H,9H2,1H3;2*1H/t5-;;/m1../s1
    • InChI Key: UFFPOOKKWWDFDY-ZJIMSODOSA-N
    • SMILES: BrC1C=C(C=CN=1)[C@@H](C)N.Cl.Cl

Computed Properties

  • Exact Mass: 271.94827g/mol
  • Monoisotopic Mass: 271.94827g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 108
  • Covalently-Bonded Unit Count: 3
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 38.9

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(R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride Related Literature

Additional information on (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride

Introduction to (R)-1-(2-Bromopyridin-4-yl)ethanamine Dihydrochloride (CAS No. 1391423-76-9)

Chemical compounds play a pivotal role in the advancement of pharmaceutical research and development, particularly in the synthesis of novel therapeutic agents. Among these, (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride, identified by its CAS number 1391423-76-9, has garnered significant attention due to its unique structural properties and potential applications in medicinal chemistry. This compound, characterized by its chiral center and brominated pyridine moiety, presents a promising scaffold for the design of bioactive molecules.

The molecular structure of (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride consists of a pyridine ring substituted at the 2-position with a bromine atom and at the 4-position with an amine group linked to an ethyl chain. The dihydrochloride salt form enhances its solubility in aqueous solutions, making it more suitable for various biochemical assays and drug formulation studies. The presence of a stereogenic center at the amine-bearing carbon atom contributes to the compound's enantiomeric purity, which is crucial for evaluating its pharmacological activity and potential side effects.

In recent years, there has been a growing interest in the development of small-molecule inhibitors targeting specific biological pathways. The bromopyridine scaffold is particularly relevant in this context, as it has been extensively explored in the design of kinase inhibitors, antiviral agents, and anti-inflammatory drugs. Research studies have demonstrated that compounds featuring this motif exhibit potent interactions with biological targets due to their ability to mimic natural substrates or interfere with key enzymatic processes.

One of the most compelling aspects of (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride is its potential as a building block for further chemical modifications. The bromine atom at the 2-position of the pyridine ring provides a versatile handle for introducing additional functional groups through cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings. These reactions are widely employed in synthetic organic chemistry to construct complex molecular architectures with tailored biological properties.

Recent advancements in medicinal chemistry have highlighted the importance of chirality in drug design. Enantiomerically pure compounds often exhibit distinct pharmacological profiles compared to their racemic counterparts, necessitating rigorous stereochemical control during synthesis. The (R)-configuration of the amine group in this compound ensures high enantiomeric purity, which is essential for optimizing its therapeutic efficacy and minimizing off-target effects.

The pharmacological potential of (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride has been explored in several preclinical studies. Researchers have investigated its interactions with various enzymes and receptors, including those involved in cancer signaling pathways, neurodegenerative diseases, and infectious diseases. Preliminary findings suggest that this compound may exhibit inhibitory activity against certain kinases, potentially making it a valuable candidate for developing novel antitumor agents.

In addition to its kinase inhibition properties, the bromopyridine moiety has been shown to interact with other biological targets such as bacterial enzymes and viral proteases. This broad spectrum of activity makes (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride a versatile lead compound for drug discovery efforts targeting multiple disease indications.

The synthesis of this compound involves multi-step organic transformations that require careful optimization to ensure high yield and purity. Key synthetic steps include the preparation of the chiral auxiliary for stereoselective amine formation, followed by bromination of the pyridine ring and subsequent coupling reactions to introduce the ethyl chain. Advanced spectroscopic techniques such as NMR and mass spectrometry are employed to monitor reaction progress and confirm structural integrity.

The solubility profile of (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride is another critical factor that influences its applicability in pharmaceutical formulations. The dihydrochloride salt form enhances water solubility, facilitating its use in aqueous-based drug delivery systems. This property is particularly advantageous for intravenous administration or oral formulations where solubility plays a key role in bioavailability.

Future research directions may focus on exploring derivatives of (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride to enhance its pharmacological properties further. Structural modifications such as replacing the ethyl chain with other alkyl or aryl groups could alter binding affinities and selectivity profiles. Additionally, investigating prodrug strategies might improve metabolic stability and bioavailability while maintaining therapeutic efficacy.

In conclusion, (R)-1-(2-Bromopyridin-4-yl)ethanamine dihydrochloride (CAS No. 1391423-76-9) represents a promising compound with significant potential in pharmaceutical research. Its unique structural features, including chirality and functional diversity provided by the brominated pyridine moiety, make it an attractive scaffold for designing novel bioactive molecules. Ongoing studies continue to unravel its pharmacological significance across various disease areas, paving the way for innovative therapeutic interventions.

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