Cas no 19854-23-0 (4-Methyl-2-(trimethylsilyl)pyridine)

4-Methyl-2-(trimethylsilyl)pyridine is a silylated pyridine derivative characterized by the presence of a trimethylsilyl group at the 2-position and a methyl substituent at the 4-position of the pyridine ring. This compound is primarily utilized as an intermediate in organic synthesis, particularly in the preparation of heterocyclic compounds and functionalized pyridines. The trimethylsilyl group enhances reactivity in cross-coupling reactions and serves as a protecting group for sensitive functionalities. Its stability and compatibility with various reaction conditions make it a valuable reagent in medicinal chemistry and materials science. The compound is typically handled under inert conditions due to its sensitivity to moisture and air.
4-Methyl-2-(trimethylsilyl)pyridine structure
19854-23-0 structure
Product Name:4-Methyl-2-(trimethylsilyl)pyridine
CAS No:19854-23-0
MF:C9H15NSi
MW:165.307603120804
CID:123810
PubChem ID:15169002
Update Time:2025-05-22

4-Methyl-2-(trimethylsilyl)pyridine Chemical and Physical Properties

Names and Identifiers

    • 4-Methyl-2-(trimethylsilyl)pyridine
    • Pyridine, 4-methyl-2-(trimethylsilyl)- (9CI)
    • Pyridine,4-methyl-2-(trimethylsilyl)-
    • trimethyl-(4-methylpyridin-2-yl)silane
    • 2-(Trimethylsilyl)-4-methyl-pyridin
    • 4-methyl-2-trimethylsilanyl-pyridine
    • 4-methyl-2-trimethylsilylpyridine
    • Pyridine,4-methyl-2-(trimethylsilyl)
    • F72199
    • MFCD21604783
    • 19854-23-0
    • J-524108
    • Pyridine, 4-methyl-2-(trimethylsilyl)-
    • DTXSID50569475
    • DB-289430
    • Inchi: 1S/C9H15NSi/c1-8-5-6-10-9(7-8)11(2,3)4/h5-7H,1-4H3
    • InChI Key: TWKKSILJXRSVBV-UHFFFAOYSA-N
    • SMILES: [Si](C)(C)(C)C1C=C(C)C=CN=1

Computed Properties

  • Exact Mass: 165.09700
  • Monoisotopic Mass: 165.097376017g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 128
  • 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
  • Topological Polar Surface Area: 12.9?2

Experimental Properties

  • PSA: 12.89000
  • LogP: 1.93520

4-Methyl-2-(trimethylsilyl)pyridine Customs Data

  • HS CODE:2933399090
  • Customs Data:

    China Customs Code:

    2933399090

    Overview:

    2933399090. Other compounds with non fused pyridine rings in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on 4-Methyl-2-(trimethylsilyl)pyridine

Recent Advances in the Application of 4-Methyl-2-(trimethylsilyl)pyridine (CAS: 19854-23-0) in Chemical Biology and Pharmaceutical Research

4-Methyl-2-(trimethylsilyl)pyridine (CAS: 19854-23-0) is a versatile organosilicon compound that has garnered significant attention in recent years due to its unique chemical properties and potential applications in chemical biology and pharmaceutical research. This compound, characterized by the presence of a trimethylsilyl group at the 2-position of the pyridine ring, serves as a valuable building block in organic synthesis and drug discovery. Recent studies have explored its utility in various contexts, including as a ligand in catalytic systems, a precursor for bioactive molecules, and a probe for studying biological systems.

One of the most notable advancements in the application of 4-Methyl-2-(trimethylsilyl)pyridine is its role in the development of novel catalytic systems. Researchers have demonstrated its effectiveness as a ligand in transition metal-catalyzed reactions, particularly in cross-coupling reactions that are pivotal for constructing complex molecular architectures. For instance, a 2023 study published in the Journal of Organic Chemistry highlighted its use in palladium-catalyzed Suzuki-Miyaura couplings, where it exhibited superior stability and reactivity compared to traditional ligands. This finding opens new avenues for the synthesis of pharmaceuticals and agrochemicals.

In addition to its catalytic applications, 4-Methyl-2-(trimethylsilyl)pyridine has been investigated as a precursor for the synthesis of biologically active compounds. A recent study in Bioorganic & Medicinal Chemistry Letters reported the successful incorporation of this compound into the scaffold of potential kinase inhibitors. The trimethylsilyl group was found to enhance the lipophilicity and metabolic stability of the resulting molecules, thereby improving their pharmacokinetic profiles. This research underscores the compound's potential in drug design, particularly for targets that require modulation of hydrophobic interactions.

Another emerging area of interest is the use of 4-Methyl-2-(trimethylsilyl)pyridine as a chemical probe for studying biological systems. Its unique spectroscopic properties, including a distinct NMR signature, make it an attractive tool for labeling and tracking small molecules in complex biological matrices. A 2022 publication in Chemical Communications detailed its application in fluorescence-based assays for detecting enzyme activity, showcasing its utility in high-throughput screening and diagnostic development.

Despite these promising developments, challenges remain in the widespread adoption of 4-Methyl-2-(trimethylsilyl)pyridine. Issues such as scalability of synthesis, cost-effectiveness, and potential toxicity need to be addressed. However, ongoing research efforts are focused on optimizing synthetic routes and exploring safer derivatives. For example, a recent patent application disclosed a novel, greener synthesis method that reduces the use of hazardous reagents while maintaining high yields.

In conclusion, 4-Methyl-2-(trimethylsilyl)pyridine (CAS: 19854-23-0) represents a valuable tool in chemical biology and pharmaceutical research, with applications ranging from catalysis to drug discovery and diagnostics. Its unique structural features and reactivity profile continue to inspire innovative research, and future studies are expected to further expand its utility. As the field progresses, interdisciplinary collaborations will be key to unlocking the full potential of this compound in addressing unmet medical needs.

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