Cas no 588717-94-6 (1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl-)

1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl-, is a boronic ester derivative commonly employed in Suzuki-Miyaura cross-coupling reactions. Its key advantages include enhanced stability under ambient conditions compared to boronic acids, reducing the need for stringent handling. The tetramethyl substitution on the dioxaborolane ring improves solubility in organic solvents, facilitating reaction setup. The 6-methoxy-1-naphthalenyl moiety serves as a versatile aryl precursor in pharmaceutical and materials science applications. This compound’s robust shelf life and consistent reactivity make it a reliable intermediate for constructing complex aromatic frameworks. Its utility is further underscored by its compatibility with a broad range of coupling partners under mild conditions.
1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- structure
588717-94-6 structure
Product Name:1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl-
CAS No:588717-94-6
MF:C17H21BO3
MW:284.157845258713
MDL:MFCD22494563
CID:1614835
PubChem ID:22240230
Update Time:2025-06-15

1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- Chemical and Physical Properties

Names and Identifiers

    • 1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl-
    • 2-(6-methoxynaphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 2-(6-Methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
    • SB37810
    • AT25632
    • DB-136648
    • LRUMIJPWNGXDQH-UHFFFAOYSA-N
    • 3-Hydroxy-3-methyloctanoic acid ethyl ester
    • 588717-94-6
    • 2-(6-methoxynaphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
    • (6-METHOXYNAPHTHALEN-1-YL)BORONIC ACID PINACOL ESTER
    • SCHEMBL5780896
    • DTXSID40623717
    • MFCD22494563
    • MDL： MFCD22494563
    • Inchi： 1S/C17H21BO3/c1-16(2)17(3,4)21-18(20-16)15-8-6-7-12-11-13(19-5)9-10-14(12)15/h6-11H,1-5H3
    • InChI Key： LRUMIJPWNGXDQH-UHFFFAOYSA-N
    • SMILES： O1B(C2=CC=CC3C=C(C=CC2=3)OC)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 283.16203
  • Monoisotopic Mass: 284.1583747g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 2
  • Complexity: 366
  • 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: 27.7?2

Experimental Properties

  • PSA: 27.69

1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- Pricemore >>

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JIE DA WEI （ SHANG HAI ） YI YAO KE JI FA ZHAN Co., Ltd.
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1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- Related Literature

Related Categories

Additional information on 1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl-

Recent Advances in the Study of 1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- (CAS: 588717-94-6)

The compound 1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- (CAS: 588717-94-6) has garnered significant attention in recent years due to its versatile applications in medicinal chemistry and drug development. This boronic ester derivative is particularly notable for its role as a key intermediate in the synthesis of biologically active molecules, including proteasome inhibitors and other therapeutic agents. Recent studies have focused on optimizing its synthetic routes, exploring its reactivity, and evaluating its potential in targeted drug delivery systems.

One of the most promising areas of research involves the use of this compound in the development of boron-containing drugs, which leverage the unique properties of boron to enhance drug efficacy and selectivity. For instance, its incorporation into proteasome inhibitors has shown improved pharmacokinetic profiles and reduced off-target effects. Additionally, the compound's stability and reactivity make it an attractive candidate for Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic chemistry.

Recent publications have also highlighted the compound's potential in imaging and diagnostics. Its fluorescent properties, derived from the naphthalene moiety, enable its use as a probe for detecting specific biomolecules in complex biological systems. This dual functionality—therapeutic and diagnostic—positions it as a valuable tool in the emerging field of theranostics.

Despite these advancements, challenges remain in scaling up the synthesis of 1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- and ensuring its stability under physiological conditions. Ongoing research aims to address these issues by developing novel protective groups and optimizing reaction conditions. Furthermore, computational studies are being employed to predict its behavior in biological systems, thereby guiding experimental design.

In conclusion, the compound 1,3,2-Dioxaborolane, 2-(6-methoxy-1-naphthalenyl)-4,4,5,5-tetramethyl- (CAS: 588717-94-6) represents a promising avenue for future research in medicinal chemistry. Its multifaceted applications, from drug development to diagnostics, underscore its importance in the field. Continued exploration of its properties and potential will likely yield innovative solutions to current challenges in healthcare and biotechnology.

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