Cas no 2227766-59-6 (rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine)

Technical Introduction: rac-(1R,2R)-2-(5-Bromopyridin-3-yl)cyclopropylmethanamine is a chiral cyclopropylamine derivative featuring a 5-bromopyridin-3-yl substituent. This compound serves as a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of bioactive molecules. The cyclopropane ring enhances conformational rigidity, while the bromopyridine moiety offers versatile reactivity for further functionalization, such as cross-coupling reactions. Its stereochemistry (rac-(1R,2R)) makes it suitable for enantioselective studies or as a precursor for optically active compounds. The amine group provides a handle for derivatization, enabling applications in drug discovery and ligand design. This product is characterized by high purity and stability, ensuring reliable performance in synthetic workflows.
rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine structure
2227766-59-6 structure
Product Name:rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine
CAS No:2227766-59-6
MF:C9H11BrN2
MW:227.101041078568
CID:6105078
PubChem ID:165642444
Update Time:2025-08-04

rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine Chemical and Physical Properties

Names and Identifiers

    • rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine
    • 2227766-59-6
    • EN300-1907159
    • rac-[(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropyl]methanamine
    • Inchi: 1S/C9H11BrN2/c10-8-1-7(4-12-5-8)9-2-6(9)3-11/h1,4-6,9H,2-3,11H2/t6-,9+/m0/s1
    • InChI Key: VRBOAOQWRRKMHC-IMTBSYHQSA-N
    • SMILES: BrC1=CN=CC(=C1)[C@@H]1C[C@H]1CN

Computed Properties

  • Exact Mass: 226.01056g/mol
  • Monoisotopic Mass: 226.01056g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 163
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1
  • Topological Polar Surface Area: 38.9?2

rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine Pricemore >>

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Additional information on rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine

Research Brief on rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine (CAS: 2227766-59-6)

Recent advancements in chemical biology and pharmaceutical research have highlighted the significance of rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine (CAS: 2227766-59-6) as a promising compound in drug discovery. This research brief synthesizes the latest findings on its synthesis, pharmacological properties, and potential therapeutic applications, providing a comprehensive overview for professionals in the field.

The compound, characterized by its cyclopropylmethanamine core and 5-bromopyridin-3-yl substituent, has garnered attention due to its unique structural features and bioactivity. Recent studies have focused on optimizing its synthetic pathways to improve yield and purity, with notable progress in enantioselective synthesis techniques. These advancements are critical for scaling up production for preclinical and clinical studies.

Pharmacological evaluations of rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine have revealed its potential as a modulator of central nervous system (CNS) targets. Preliminary in vitro and in vivo studies suggest its affinity for specific neurotransmitter receptors, implicating its utility in treating neurological disorders such as depression and anxiety. However, further mechanistic studies are required to elucidate its exact mode of action and selectivity.

In addition to its CNS applications, recent research has explored the compound's role in oncology. Its bromopyridine moiety has been linked to inhibitory effects on certain kinase enzymes involved in cancer cell proliferation. Early-stage cell-based assays demonstrate promising cytotoxicity against select cancer cell lines, warranting further investigation into its therapeutic potential and safety profile.

The development of rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine also underscores the importance of structure-activity relationship (SAR) studies. Researchers have synthesized analogs to evaluate the impact of structural modifications on bioactivity, yielding insights into key pharmacophores. These findings are instrumental in guiding the design of next-generation derivatives with enhanced efficacy and reduced off-target effects.

Despite these promising developments, challenges remain in the clinical translation of this compound. Issues such as bioavailability, metabolic stability, and potential toxicity need to be addressed through rigorous preclinical testing. Collaborative efforts between academic institutions and pharmaceutical companies are essential to accelerate its progression through the drug development pipeline.

In conclusion, rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine represents a compelling candidate for further research in both CNS and oncology therapeutics. Its multifaceted bioactivity and ongoing synthetic optimizations position it as a valuable asset in the quest for novel pharmacotherapies. Continued interdisciplinary research will be pivotal in unlocking its full therapeutic potential.

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