Cas no 15936-06-8 (3-(Bromomethyl)-2-nitropyridine)

3-(Bromomethyl)-2-nitropyridine is a versatile brominated nitropyridine derivative commonly employed as an intermediate in organic synthesis and pharmaceutical research. Its reactive bromomethyl group facilitates selective alkylation or substitution reactions, while the nitro group enhances electrophilic properties, making it useful for further functionalization. This compound is particularly valuable in the preparation of heterocyclic compounds, agrochemicals, and active pharmaceutical ingredients (APIs). Its well-defined reactivity and stability under controlled conditions ensure consistent performance in synthetic applications. Proper handling is advised due to its potential sensitivity to moisture and light. Suitable for use in controlled laboratory environments by trained professionals.
3-(Bromomethyl)-2-nitropyridine structure
15936-06-8 structure
Product Name:3-(Bromomethyl)-2-nitropyridine
CAS No:15936-06-8
MF:C6H5BrN2O2
MW:217.020100355148
MDL:MFCD14584511
CID:2134558
PubChem ID:21271175
Update Time:2025-05-19

3-(Bromomethyl)-2-nitropyridine Chemical and Physical Properties

Names and Identifiers

    • 3-(bromomethyl)-2-nitroPyridine
    • OQMKZWDHHRRWNF-UHFFFAOYSA-N
    • FCH1385145
    • OR200119
    • 3-(Bromomethyl)-2-nitropyridine
    • MDL: MFCD14584511
    • Inchi: 1S/C6H5BrN2O2/c7-4-5-2-1-3-8-6(5)9(10)11/h1-3H,4H2
    • InChI Key: OQMKZWDHHRRWNF-UHFFFAOYSA-N
    • SMILES: BrCC1=CC=CN=C1[N+](=O)[O-]

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 148
  • Topological Polar Surface Area: 58.7

3-(Bromomethyl)-2-nitropyridine Pricemore >>

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Additional information on 3-(Bromomethyl)-2-nitropyridine

Recent Advances in the Application of 3-(Bromomethyl)-2-nitropyridine (CAS: 15936-06-8) in Chemical Biology and Pharmaceutical Research

3-(Bromomethyl)-2-nitropyridine (CAS: 15936-06-8) is a versatile chemical intermediate that has garnered significant attention in recent years due to its applications in medicinal chemistry, drug discovery, and chemical biology. This heterocyclic compound, characterized by a reactive bromomethyl group and a nitro substituent, serves as a key building block for the synthesis of various bioactive molecules. Recent studies have explored its utility in developing novel kinase inhibitors, antimicrobial agents, and targeted covalent inhibitors, highlighting its importance in modern pharmaceutical research.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of 3-(Bromomethyl)-2-nitropyridine as a precursor for synthesizing potent and selective JAK3 inhibitors. The researchers utilized the bromomethyl group for efficient functionalization, enabling the creation of a diverse library of compounds with improved pharmacokinetic properties. This work underscores the compound's role in addressing the challenges of kinase inhibitor selectivity, a critical issue in autoimmune disease and cancer therapy.

In the field of antibacterial drug development, a recent breakthrough published in ACS Infectious Diseases (2024) reported the design of novel quinolone derivatives using 3-(Bromomethyl)-2-nitropyridine as a key intermediate. The resulting compounds showed remarkable activity against drug-resistant Gram-positive pathogens, with MIC values in the low micromolar range. The nitro group in particular was found to enhance bacterial membrane penetration, while the bromomethyl moiety allowed for strategic modifications to reduce cytotoxicity.

From a chemical biology perspective, innovative applications have emerged in protein labeling and targeted covalent modification. A Nature Chemical Biology paper (2023) described a novel bioconjugation strategy where 3-(Bromomethyl)-2-nitropyridine derivatives were engineered as electrophilic warheads for selective cysteine modification. This approach enabled precise mapping of protein-protein interaction interfaces and the development of activity-based probes for studying enzyme function in complex biological systems.

The synthetic versatility of 3-(Bromomethyl)-2-nitropyridine continues to expand, as evidenced by recent methodological advances. A 2024 Organic Letters publication presented a mild, transition-metal-free coupling protocol that preserves the sensitive nitro group while enabling diverse C-C bond formations. This development addresses previous limitations in handling this reactive intermediate and opens new possibilities for structure-activity relationship studies in drug discovery programs.

Looking forward, the unique reactivity profile of 3-(Bromomethyl)-2-nitropyridine positions it as a valuable tool for addressing emerging challenges in pharmaceutical research. Current investigations focus on its application in PROTAC (proteolysis targeting chimera) development and targeted protein degradation strategies, where its dual functionality offers distinct advantages for linker design. As research progresses, this compound is expected to play an increasingly important role in the development of next-generation therapeutics and chemical probes.

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