Cas no 5006-58-6 (2,3,5-Tribromo-4,6-dimethylpyridine)

2,3,5-Tribromo-4,6-dimethylpyridine is a halogenated pyridine derivative characterized by its high bromine content and stable aromatic structure. This compound is primarily utilized as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its brominated structure enhances reactivity in substitution and coupling reactions, making it valuable for constructing complex molecular frameworks. The presence of methyl groups at the 4- and 6-positions further influences its steric and electronic properties, contributing to selective reactivity. The compound is typically supplied as a crystalline solid with high purity, ensuring consistent performance in synthetic applications. Proper handling is advised due to its potential reactivity under specific conditions.
2,3,5-Tribromo-4,6-dimethylpyridine structure
5006-58-6 structure
Product Name:2,3,5-Tribromo-4,6-dimethylpyridine
CAS No:5006-58-6
MF:C7H6Br3N
MW:343.841239452362
MDL:MFCD25963793
CID:386625
PubChem ID:253291
Update Time:2025-05-21

2,3,5-Tribromo-4,6-dimethylpyridine Chemical and Physical Properties

Names and Identifiers

    • 2,3,5-Tribromo-4,6-dimethylpyridine
    • 2,3,5-Tribrom-4,6-dimethyl-pyridin
    • 2,3,5-tribromo-4,6-dimethyl-pyridine
    • AC1L5NTR
    • AC1Q25EP
    • AR-1D2144
    • CTK4J2039
    • NCIOpen2_008355
    • NSC76015
    • CHEMBL1464270
    • NSC-76015
    • NSC 76015
    • 5006-58-6
    • SMR000528339
    • MLS000736828
    • DTXSID50291507
    • Pyridine,2,3,5-tribromo-4,6-dimethyl-
    • MDL: MFCD25963793
    • Inchi: 1S/C7H6Br3N/c1-3-5(8)4(2)11-7(10)6(3)9/h1-2H3
    • InChI Key: MPTZAZNRFRQFTO-UHFFFAOYSA-N
    • SMILES: BrC1C(C)=NC(=C(C=1C)Br)Br

Computed Properties

  • Exact Mass: 340.80498
  • Monoisotopic Mass: 340.80504g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 142
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4
  • Topological Polar Surface Area: 12.9?2

Experimental Properties

  • PSA: 12.89
  • LogP: 3.98590

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Additional information on 2,3,5-Tribromo-4,6-dimethylpyridine

Recent Advances in the Study of 2,3,5-Tribromo-4,6-dimethylpyridine (CAS: 5006-58-6) in Chemical Biology and Pharmaceutical Research

2,3,5-Tribromo-4,6-dimethylpyridine (CAS: 5006-58-6) is a halogenated pyridine derivative that has recently garnered significant attention in chemical biology and pharmaceutical research due to its unique structural properties and potential applications. This compound, characterized by its three bromine atoms and two methyl groups, serves as a versatile intermediate in the synthesis of more complex molecules, particularly in the development of novel therapeutic agents and bioactive compounds. Recent studies have explored its utility in drug discovery, material science, and agrochemical applications, highlighting its broad relevance across multiple scientific disciplines.

One of the key areas of interest in recent research has been the role of 2,3,5-Tribromo-4,6-dimethylpyridine as a building block for the synthesis of heterocyclic compounds. Its brominated structure makes it a valuable precursor for cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are pivotal in medicinal chemistry for constructing pharmacologically active molecules. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy in the synthesis of brominated pyridine-based inhibitors targeting kinase enzymes, which are implicated in various cancers and inflammatory diseases.

In addition to its synthetic applications, recent investigations have delved into the biological activities of 2,3,5-Tribromo-4,6-dimethylpyridine itself. Preliminary in vitro studies suggest that this compound exhibits moderate antimicrobial properties against Gram-positive bacteria, including Staphylococcus aureus, as reported in a 2022 Bioorganic & Medicinal Chemistry Letters publication. Researchers hypothesize that the bromine atoms contribute to this activity by disrupting bacterial cell membranes or interfering with essential enzymatic processes. Further studies are underway to optimize its structure for enhanced potency and selectivity.

Another emerging application of 2,3,5-Tribromo-4,6-dimethylpyridine lies in its potential as a ligand or catalyst in asymmetric synthesis. A 2023 ACS Catalysis paper highlighted its use in palladium-catalyzed C-H activation reactions, where it facilitated the formation of chiral centers in high enantiomeric excess. This finding opens new avenues for the development of enantioselective synthetic routes, which are critical for producing optically pure pharmaceuticals.

Despite these promising developments, challenges remain in the large-scale production and environmental impact of 2,3,5-Tribromo-4,6-dimethylpyridine. Recent environmental toxicity studies, such as those published in Green Chemistry (2023), have raised concerns about the persistence and bioaccumulation potential of brominated compounds. Researchers are actively exploring greener synthetic routes and recycling methods for bromine-containing byproducts to address these issues.

Looking forward, the versatility of 2,3,5-Tribromo-4,6-dimethylpyridine (CAS: 5006-58-6) suggests it will continue to be a valuable tool in chemical biology and pharmaceutical research. Ongoing studies are investigating its potential in drug delivery systems, where its lipophilic nature could enhance membrane permeability of therapeutic agents. Furthermore, computational chemistry approaches are being employed to predict novel derivatives with improved pharmacological profiles, as described in a recent Journal of Chemical Information and Modeling article (2024).

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