Cas no 2377608-16-5 (Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate)

Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate structure
2377608-16-5 structure
Product Name:Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate
CAS No:2377608-16-5
MF:C19H22BNO4
MW:339.19328546524
CID:5085683
PubChem ID:154881562
Update Time:2025-07-22

Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate
    • AT14429
    • Benzyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
    • Benzyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate
    • 2377608-16-5
    • CS-0177554
    • XH0414
    • BS-34746
    • 2-Benzyloxycarbonylpyridine-5-boronic Acid Pinacol ester
    • Inchi: 1S/C19H22BNO4/c1-18(2)19(3,4)25-20(24-18)15-10-11-16(21-12-15)17(22)23-13-14-8-6-5-7-9-14/h5-12H,13H2,1-4H3
    • InChI Key: FRYJUEBTYNHTMT-UHFFFAOYSA-N
    • SMILES: O1B(C2C=NC(C(=O)OCC3C=CC=CC=3)=CC=2)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 339.1641883g/mol
  • Monoisotopic Mass: 339.1641883g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 5
  • Complexity: 460
  • 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: 57.6

Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate Pricemore >>

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Additional information on Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate

Comprehensive Overview of Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (CAS No. 2377608-16-5)

Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (CAS No. 2377608-16-5) is a highly specialized boronic ester derivative that has garnered significant attention in the fields of organic synthesis, pharmaceutical intermediates, and material science. This compound, characterized by its unique pyridine and dioxaborolane functional groups, serves as a versatile building block for Suzuki-Miyaura cross-coupling reactions, a cornerstone methodology in modern drug discovery and agrochemical development.

The molecular structure of Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate features a benzyl-protected carboxylate moiety and a tetramethyl dioxaborolane group, which enhances its stability and reactivity under various conditions. Researchers have leveraged this compound to synthesize complex heterocyclic compounds, which are pivotal in designing kinase inhibitors and other biologically active molecules. Its CAS No. 2377608-16-5 ensures precise identification in chemical databases, facilitating global research collaboration.

In recent years, the demand for boron-containing compounds like Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate has surged due to their role in proteolysis-targeting chimeras (PROTACs) and covalent inhibitors. These applications align with trending topics such as targeted protein degradation and precision medicine, making this compound a focal point in cutting-edge therapeutics. Additionally, its utility in OLED materials and organic electronics underscores its interdisciplinary relevance.

From a synthetic perspective, the tetramethyl-1,3,2-dioxaborolane group in this compound offers improved solubility in organic solvents compared to traditional boronic acids, simplifying purification and handling. This advantage is critical for high-throughput screening and combinatorial chemistry, where efficiency and reproducibility are paramount. The benzyl ester further provides a protective group strategy, enabling selective deprotection in multistep syntheses.

Environmental and regulatory considerations have also shaped the discourse around CAS No. 2377608-16-5. As the chemical industry shifts toward green chemistry principles, researchers are exploring solvent-free or aqueous-phase reactions involving this compound to minimize waste. Its compatibility with biocatalysis and flow chemistry further positions it as a sustainable option for industrial-scale production.

In summary, Benzyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (CAS No. 2377608-16-5) exemplifies the convergence of synthetic innovation and applied research. Its multifaceted applications—from drug development to advanced materials—highlight its enduring value in the scientific community. As interest in boron chemistry and functionalized heterocycles grows, this compound will undoubtedly remain a key player in shaping future technological breakthroughs.

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