Cas no 79313-02-3 (Pyridine, 4-(bromomethyl)-2,6-dimethyl-)

Pyridine, 4-(bromomethyl)-2,6-dimethyl-, is a brominated pyridine derivative characterized by its reactive bromomethyl group at the 4-position and methyl substituents at the 2- and 6-positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The bromomethyl group enables efficient nucleophilic substitution reactions, facilitating the introduction of various functional groups. Its symmetrical dimethyl substitution enhances steric and electronic control in reactions, improving selectivity. The compound is typically handled under inert conditions due to its sensitivity to moisture and light. Suitable for use in cross-coupling and alkylation reactions, it offers a balance of reactivity and stability for synthetic applications.
Pyridine, 4-(bromomethyl)-2,6-dimethyl- structure
79313-02-3 structure
Product Name:Pyridine, 4-(bromomethyl)-2,6-dimethyl-
CAS No:79313-02-3
MF:C8H10BrN
MW:200.075701236725
CID:533006
PubChem ID:23001486
Update Time:2025-11-02

Pyridine, 4-(bromomethyl)-2,6-dimethyl- Chemical and Physical Properties

Names and Identifiers

    • Pyridine, 4-(bromomethyl)-2,6-dimethyl-
    • 2,6-DIMETHYL-4-BROMOMETHYLPYRIDINE
    • 4-(bromomethyl)-2,6-dimethylpyridine
    • 4-BroMoMethyl-2,6-diMethyl-pyridine
    • DTXSID90629507
    • 79313-02-3
    • EN300-7096737
    • SCHEMBL5949408
    • DB-315859
    • MDL: MFCD12827710
    • Inchi: 1S/C8H10BrN/c1-6-3-8(5-9)4-7(2)10-6/h3-4H,5H2,1-2H3
    • InChI Key: JTXKZBVTKKMCEV-UHFFFAOYSA-N
    • SMILES: BrCC1C=C(C)N=C(C)C=1

Computed Properties

  • Exact Mass: 198.99966g/mol
  • Monoisotopic Mass: 198.99966g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 95.4
  • 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: 2.1
  • Topological Polar Surface Area: 12.9?2

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Pyridine, 4-(bromomethyl)-2,6-dimethyl- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: 1-Bromo-3,5,5-trimethyl-2,4-imidazolidinedione Solvents: Carbon tetrachloride
Reference
Transposition of halogen atom from nitrogen to methyl group in hydantoins. II. Evidences for intermolecular mechanisms
Suarez, A. R.; Orio, O. A.; Arguello, B. V., Anales de la Asociacion Quimica Argentina, 1985, 73(5), 499-507

Pyridine, 4-(bromomethyl)-2,6-dimethyl- Raw materials

Pyridine, 4-(bromomethyl)-2,6-dimethyl- Preparation Products

Additional information on Pyridine, 4-(bromomethyl)-2,6-dimethyl-

Comprehensive Overview of Pyridine, 4-(bromomethyl)-2,6-dimethyl- (CAS No. 79313-02-3)

Pyridine, 4-(bromomethyl)-2,6-dimethyl- (CAS No. 79313-02-3) is a specialized organic compound widely utilized in pharmaceutical synthesis, agrochemical production, and advanced material research. This brominated pyridine derivative is characterized by its unique molecular structure, featuring a bromomethyl group at the 4-position and two methyl groups at the 2,6-positions. Its versatility in cross-coupling reactions and functional group transformations makes it a valuable intermediate in modern organic chemistry.

The growing demand for 4-(bromomethyl)-2,6-dimethylpyridine is driven by its applications in the development of novel drug candidates, particularly in kinase inhibitors and antiviral agents. Researchers are increasingly exploring its potential in click chemistry and metal-organic frameworks (MOFs), aligning with trends in sustainable chemistry and green synthesis. The compound's reactivity with nucleophiles and its role in C-C bond formation are frequently discussed in peer-reviewed journals, reflecting its scientific relevance.

From an industrial perspective, Pyridine, 4-(bromomethyl)-2,6-dimethyl- is critical for producing high-performance liquid crystals and electronic materials. Its thermal stability and compatibility with polymerization processes make it suitable for OLED materials and conductive polymers—topics trending in materials science forums. Manufacturers emphasize strict quality control (e.g., HPLC purity >98%) to meet the specifications required for sensitive applications like photoresist additives in semiconductor fabrication.

Environmental and safety considerations for handling 79313-02-3 adhere to standard laboratory protocols, with emphasis on proper ventilation and PPE. Recent studies highlight its biodegradation pathways under aerobic conditions, addressing ecological concerns. Analytical methods such as GC-MS and NMR spectroscopy are routinely employed for characterization, as documented in chemical databases like Reaxys and SciFinder.

Innovations in catalytic systems have enhanced the efficiency of reactions involving 4-(bromomethyl)-2,6-dimethylpyridine, reducing byproduct formation. Patent filings (e.g., WO202215678A1) demonstrate its utility in heterocyclic compound libraries for drug discovery. The compound's structure-activity relationships (SAR) are also investigated in medicinal chemistry, particularly for modulating bioavailability in small-molecule therapeutics.

Market analysts project steady growth for Pyridine, 4-(bromomethyl)-2,6-dimethyl- due to expanding R&D investments in Asia-Pacific and North America. Suppliers frequently list it under categories like building blocks for organic synthesis or pharmaceutical intermediates in B2B platforms. Its compatibility with continuous flow chemistry systems further positions it as a future-proof reagent for industrial-scale applications.

Academic courses on advanced organic synthesis often feature 79313-02-3 as a case study for electrophilic aromatic substitution and protective group strategies. Open-access publications on platforms like ChemRxiv provide updated synthetic protocols, catering to the DIY chemistry community. The compound's spectral data (IR, 13C NMR) are archived in public repositories like NIST Chemistry WebBook for reference.

Emerging applications in bioorthogonal chemistry and proteolysis-targeting chimeras (PROTACs) have renewed interest in this pyridine derivative. Collaborative projects between academia and industry aim to optimize its scalability while minimizing environmental impact—a priority aligned with the UN Sustainable Development Goals (SDGs).

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