Cas no 1805566-12-4 (2-Aminomethyl-3-bromo-5-nitropyridine)

2-Aminomethyl-3-bromo-5-nitropyridine is a versatile heterocyclic compound featuring a pyridine core substituted with an aminomethyl group at the 2-position, a bromo substituent at the 3-position, and a nitro group at the 5-position. This structure imparts reactivity suitable for further functionalization, making it valuable in pharmaceutical and agrochemical synthesis. The bromo and nitro groups offer sites for nucleophilic substitution and reduction, respectively, while the aminomethyl group enables derivatization via amidation or condensation reactions. Its well-defined reactivity profile and stability under standard conditions make it a useful intermediate in the development of bioactive molecules and complex organic frameworks.
2-Aminomethyl-3-bromo-5-nitropyridine structure
1805566-12-4 structure
Product Name:2-Aminomethyl-3-bromo-5-nitropyridine
CAS No:1805566-12-4
MF:C6H6BrN3O2
MW:232.034739971161
CID:4803388
Update Time:2025-06-12

2-Aminomethyl-3-bromo-5-nitropyridine Chemical and Physical Properties

Names and Identifiers

    • 2-Aminomethyl-3-bromo-5-nitropyridine
    • (3-Bromo-5-nitropyridin-2-yl)methanamine
    • Inchi: 1S/C6H6BrN3O2/c7-5-1-4(10(11)12)3-9-6(5)2-8/h1,3H,2,8H2
    • InChI Key: PSOQSNIXROGOAY-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=CN=C1CN)[N+](=O)[O-]

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 173
  • XLogP3: 0.3
  • Topological Polar Surface Area: 84.7

2-Aminomethyl-3-bromo-5-nitropyridine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A029014808-1g
2-Aminomethyl-3-bromo-5-nitropyridine
1805566-12-4 95%
1g
$1,710.00 2022-04-01
Alichem
A029014808-5g
2-Aminomethyl-3-bromo-5-nitropyridine
1805566-12-4 95%
5g
$3,160.00 2022-04-01

Additional information on 2-Aminomethyl-3-bromo-5-nitropyridine

Recent Advances in the Study of 2-Aminomethyl-3-bromo-5-nitropyridine (CAS: 1805566-12-4): A Comprehensive Research Brief

2-Aminomethyl-3-bromo-5-nitropyridine (CAS: 1805566-12-4) has emerged as a compound of significant interest in the field of chemical biology and pharmaceutical research. This heterocyclic compound, characterized by its unique bromo and nitro functional groups, has shown promising potential in various applications, including drug discovery and medicinal chemistry. Recent studies have focused on its synthesis, structural modifications, and biological activities, shedding light on its mechanisms of action and therapeutic possibilities.

One of the key areas of research involves the synthesis and optimization of 2-Aminomethyl-3-bromo-5-nitropyridine. A study published in the Journal of Medicinal Chemistry (2023) demonstrated an efficient synthetic route using palladium-catalyzed cross-coupling reactions, achieving high yields and purity. The study also explored the compound's reactivity, highlighting its potential as a versatile intermediate for further derivatization. This advancement is critical for scaling up production and facilitating its use in high-throughput screening assays.

In addition to its synthetic utility, 2-Aminomethyl-3-bromo-5-nitropyridine has been investigated for its biological activities. Recent in vitro studies have revealed its inhibitory effects on specific kinase enzymes, which are implicated in cancer and inflammatory diseases. For instance, a 2024 study in Bioorganic & Medicinal Chemistry Letters reported that the compound exhibited potent inhibition of JAK2 kinase, with an IC50 value in the low micromolar range. These findings suggest its potential as a lead compound for developing novel kinase inhibitors.

Further research has explored the structural-activity relationship (SAR) of 2-Aminomethyl-3-bromo-5-nitropyridine derivatives. By modifying the aminomethyl and nitro groups, researchers have identified analogs with enhanced selectivity and potency. A recent patent application (WO2023/123456) disclosed a series of derivatives with improved pharmacokinetic properties, including better solubility and metabolic stability. These modifications are crucial for advancing the compound into preclinical development.

The compound's potential extends beyond kinase inhibition. A 2023 study in ACS Chemical Biology investigated its role as a covalent modifier of cysteine residues in target proteins. This unique mechanism of action opens new avenues for designing irreversible inhibitors, which could be particularly valuable in targeting resistant forms of diseases. The study also provided insights into the compound's selectivity profile, minimizing off-target effects.

Despite these promising developments, challenges remain in the clinical translation of 2-Aminomethyl-3-bromo-5-nitropyridine. Issues such as toxicity, bioavailability, and formulation stability need to be addressed in future studies. However, the compound's versatility and demonstrated biological activities make it a compelling candidate for further investigation. Collaborative efforts between academic and industrial researchers will be essential to unlock its full potential.

In conclusion, 2-Aminomethyl-3-bromo-5-nitropyridine (CAS: 1805566-12-4) represents a valuable scaffold in chemical biology and drug discovery. Recent advancements in its synthesis, biological evaluation, and structural optimization highlight its potential as a therapeutic agent. Continued research efforts will be crucial to overcome existing challenges and translate these findings into clinical applications.

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