Cas no 1622217-32-6 (4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester)

4,6-Dimethylpyridine-3-boronic acid pinacol ester is a boronic ester derivative commonly employed in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity. The pinacol ester group enhances shelf life and handling by protecting the boronic acid moiety from hydrolysis. The dimethylpyridine scaffold provides a sterically and electronically tunable framework for constructing heterocyclic compounds in pharmaceutical and materials chemistry. This reagent is particularly valued for its compatibility with mild reaction conditions and its ability to facilitate the synthesis of complex biaryl structures. Its crystalline solid form ensures consistent purity and ease of quantification in synthetic applications.
4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester structure
1622217-32-6 structure
Product Name:4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester
CAS No:1622217-32-6
MF:C13H20BNO2
MW:233.11440372467
MDL:MFCD18719934
CID:2601939
PubChem ID:86222895
Update Time:2025-06-14

4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester Chemical and Physical Properties

Names and Identifiers

    • 4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester
    • APXPNTIPURIKQY-UHFFFAOYSA-N
    • CS-0439595
    • 2,4-DIMETHYLPYRIDINE-5-BORONIC ACID PINACOL ESTER
    • CS-33154
    • 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
    • C90592
    • DB-148859
    • AC4614
    • SY029188
    • MFCD18719934
    • 1622217-32-6
    • MDL: MFCD18719934
    • Inchi: 1S/C13H20BNO2/c1-9-7-10(2)15-8-11(9)14-16-12(3,4)13(5,6)17-14/h7-8H,1-6H3
    • InChI Key: APXPNTIPURIKQY-UHFFFAOYSA-N
    • SMILES: O1B(C2C=NC(C)=CC=2C)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 233.1587090Da
  • Monoisotopic Mass: 233.1587090Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 1
  • Complexity: 277
  • 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: 31.4?2

4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester Pricemore >>

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4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester Related Literature

Additional information on 4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester

Comprehensive Guide to 4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester (CAS No. 1622217-32-6): Properties, Applications, and Industry Insights

4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester (CAS No. 1622217-32-6) is a high-value boronic ester derivative widely utilized in pharmaceutical research, organic synthesis, and material science. This compound belongs to the pyridine-boronic acid family, known for its stability and versatility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern drug discovery. With the rise of targeted drug development and green chemistry, demand for specialized boron-containing intermediates like this has surged, making it a focal point for researchers and manufacturers alike.

The molecular structure of 4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester features a pinacol-protected boronate group at the 3-position of a dimethyl-substituted pyridine ring. This design enhances its shelf stability while maintaining reactivity under catalytic conditions. Recent studies highlight its role in synthesizing heterocyclic compounds, particularly in oncology and CNS drug candidates. A 2023 Journal of Medicinal Chemistry report emphasized its utility in constructing kinase inhibitor scaffolds, addressing trending searches like "next-generation cancer therapeutics" and "small molecule drug design."

From an industrial perspective, this compound aligns with the growing emphasis on sustainable synthetic routes. Its compatibility with palladium-free coupling systems answers frequent queries about "transition metal alternatives in catalysis." Manufacturers now prioritize high-purity grades (≥98%) to meet stringent GMP standards, reflecting the pharmaceutical industry's shift toward quality-by-design (QbD) principles – a hot topic in process chemistry forums.

Analytical characterization of CAS No. 1622217-32-6 typically involves HPLC-MS and NMR spectroscopy, with particular attention to boron-11 NMR for verifying ester integrity. Storage recommendations (-20°C under inert gas) frequently appear in technical FAQs, underscoring users' concerns about compound stability. Notably, its low hygroscopicity compared to free boronic acids makes it preferable for automated synthesis platforms – a key advantage for labs investing in high-throughput screening infrastructure.

Emerging applications include OLED material synthesis, where its electron-deficient pyridine core contributes to charge transport layers. This connects with booming interest in "organic electronic materials" and "flexible display technologies." Patent analyses reveal a 40% increase in filings referencing this compound since 2020, particularly in photovoltaic materials and bioimaging probes – areas dominating materials science search trends.

For procurement specialists, understanding supply chain dynamics is crucial. Major producers have implemented just-in-time manufacturing to address the compound's specialty chemical status. Pricing trends correlate with boron feedstock availability, a topic gaining traction amid discussions about critical raw material security. Regulatory-wise, proper REACH compliance documentation remains essential, reflecting the industry's focus on regulatory preparedness in chemical sourcing.

In academic settings, 4,6-Dimethylpyridine-3-boronic Acid Pinacol Ester serves as an excellent case study for organoboron chemistry courses. Its crystallographic data (CCDC-deposited) facilitates molecular modeling exercises, addressing pedagogical searches like "teaching Suzuki coupling" and "hands-on medicinal chemistry." The compound's moderate polarity also makes it ideal for demonstrating chromatographic purification techniques.

Future directions may involve continuous flow chemistry adaptations, as evidenced by recent microwave-assisted coupling studies. With the boron therapeutics market projected to reach $2.5B by 2027 (Grand View Research), derivatives like this will likely see expanded use in proteolysis-targeting chimeras (PROTACs) and covalent inhibitor development – two of the most searched drug modality topics today.

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