Cas no 173999-33-2 (3-bromo-5-(bromomethyl)pyridine hydrobromide)

3-Bromo-5-(bromomethyl)pyridine hydrobromide is a brominated pyridine derivative with significant utility in organic synthesis and pharmaceutical research. Its key advantages include its role as a versatile intermediate for constructing complex heterocyclic frameworks, owing to the reactivity of both the bromomethyl and bromo substituents. The hydrobromide salt form enhances stability and handling, making it suitable for controlled reactions. This compound is particularly valuable in cross-coupling reactions, nucleophilic substitutions, and as a precursor for functionalized pyridines. Its well-defined structure and high purity ensure reproducibility in synthetic applications, supporting advancements in medicinal chemistry and material science.
3-bromo-5-(bromomethyl)pyridine hydrobromide structure
173999-33-2 structure
Product Name:3-bromo-5-(bromomethyl)pyridine hydrobromide
CAS No:173999-33-2
MF:C6H6Br3N
MW:331.830539226532
CID:4612670
PubChem ID:75480686
Update Time:2025-06-07

3-bromo-5-(bromomethyl)pyridine hydrobromide Chemical and Physical Properties

Names and Identifiers

    • 3-bromo-5-(bromomethyl)pyridine hydrobromide
    • Inchi: 1S/C6H5Br2N.BrH/c7-2-5-1-6(8)4-9-3-5;/h1,3-4H,2H2;1H
    • InChI Key: BPOFPXZAYNLKPH-UHFFFAOYSA-N
    • SMILES: C(C1=CN=CC(Br)=C1)Br.Br

3-bromo-5-(bromomethyl)pyridine hydrobromide Pricemore >>

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Additional information on 3-bromo-5-(bromomethyl)pyridine hydrobromide

Introduction to 3-bromo-5-(bromomethyl)pyridine hydrobromide (CAS No. 173999-33-2)

3-bromo-5-(bromomethyl)pyridine hydrobromide is a significant compound in the realm of pharmaceutical and chemical research, characterized by its unique molecular structure and versatile reactivity. This compound, identified by the CAS number 173999-33-2, has garnered considerable attention due to its potential applications in the synthesis of various bioactive molecules. The presence of both bromo and methyl substituents on a pyridine backbone enhances its utility as a building block in medicinal chemistry, particularly in the development of novel therapeutic agents.

The compound's structure consists of a pyridine ring substituted at the 3rd and 5th positions with bromine and a bromomethyl group, respectively. This arrangement imparts distinct chemical properties that make it valuable for further functionalization. The hydrobromide salt form enhances its solubility in polar solvents, facilitating its use in various synthetic protocols. In recent years, the demand for such heterocyclic compounds has surged, driven by their role in drug discovery and development.

One of the most compelling aspects of 3-bromo-5-(bromomethyl)pyridine hydrobromide is its utility as an intermediate in the synthesis of more complex molecules. Researchers have leveraged its reactive sites to introduce additional functional groups, leading to the creation of diverse pharmacophores. For instance, the bromomethyl group can undergo nucleophilic addition reactions, while the bromine atoms can be displaced through metal-catalyzed cross-coupling reactions such as Suzuki or Buchwald-Hartwig couplings. These transformations have enabled the construction of intricate molecular architectures essential for designing new drugs.

In the context of contemporary pharmaceutical research, this compound has found applications in the synthesis of kinase inhibitors, which are critical for treating cancers and inflammatory diseases. The pyridine scaffold is a common motif in many kinase inhibitors due to its ability to interact favorably with biological targets. By modifying the substituents on the pyridine ring, chemists can fine-tune the binding affinity and selectivity of their compounds. The work of several research groups has demonstrated that derivatives of 3-bromo-5-(bromomethyl)pyridine hydrobromide exhibit promising activity against various kinases, highlighting its importance as a lead compound.

Moreover, advancements in computational chemistry have further enhanced the utility of this compound. Molecular modeling studies have been instrumental in predicting how different derivatives might interact with biological targets. These studies often involve generating 3D structures of potential drug candidates and evaluating their binding modes through virtual screening. The insights gained from such simulations have guided experimental efforts, leading to more efficient synthetic routes and improved drug candidates.

The pharmaceutical industry has also shown interest in exploring the antimicrobial properties of compounds derived from 3-bromo-5-(bromomethyl)pyridine hydrobromide. Pyridine-based molecules have long been recognized for their ability to disrupt bacterial cell membranes or inhibit essential metabolic pathways. Recent studies have reported novel derivatives that exhibit potent activity against multidrug-resistant strains of bacteria. This has been particularly noteworthy given the growing crisis of antibiotic resistance worldwide. The ability to design new antimicrobial agents using this compound as a starting point represents a significant advancement in combating infectious diseases.

Another area where this compound has made an impact is in materials science. Beyond its biological applications, 3-bromo-5-(bromomethyl)pyridine hydrobromide has been utilized in the synthesis of organic semiconductors and luminescent materials. The pyridine ring's electronic properties make it suitable for tuning the optoelectronic characteristics of materials used in organic light-emitting diodes (OLEDs) and photovoltaic cells. Researchers have incorporated derivatives into polymer backbones to create materials with enhanced charge transport properties, contributing to more efficient electronic devices.

The synthesis of 3-bromo-5-(bromomethyl)pyridine hydrobromide itself is another area of active research. Efficient synthetic routes are crucial for producing this compound on a scale that meets industrial demands. One such method involves starting from commercially available pyridine derivatives and employing sequential halogenation and functionalization steps. Recent improvements in synthetic methodologies have focused on minimizing side reactions and maximizing yields, ensuring a reliable supply for downstream applications.

In conclusion, 3-bromo-5-(bromomethyl)pyridine hydrobromide (CAS No. 173999-33-2) stands out as a versatile and valuable compound with broad applications across multiple scientific disciplines. Its role as a key intermediate in pharmaceutical synthesis, particularly for kinase inhibitors and antimicrobial agents, underscores its importance in drug discovery efforts. Additionally, its utility in materials science highlights its potential beyond traditional medicinal chemistry applications. As research continues to uncover new uses for this compound, it will undoubtedly remain a cornerstone in both academic and industrial settings.

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