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3-Methoxynaphthalene-2-boronic acid

  • CAS No. 104115-76-6

  • Cat. No. CS-0037483
  • Purity≥98%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

3-Methoxynaphthalene-2-boronic acid|CS-0037483

Structure of 104115-76-6

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General Information

  • CAS No. 104115-76-6
  • Cat. No. CS-0037483
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₁BO₃
  • Molecular Weight 202.01
  • Synonym(s) 3-Methoxynaphthalen-2-yl-2-ylboronic acid
  • SMILES COC1=C(C=C2C=CC=CC2=C1)B(O)O

Description

3-Methoxynaphthalene-2-boronic acid features a boronic acid group fused to a naphthalene core with a methoxy substituent at the 3-position. This electron-rich scaffold enables efficient cross-coupling reactions under mild conditions, offering enhanced solubility and stability in aqueous-organic media. The strategic placement of the methoxy group modulates reactivity and facilitates downstream functionalization in synthetic sequences.

Application

3-Methoxynaphthalene-2-boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl scaffolds under mild conditions. The methoxy group enhances solubility and electronic modulation, while the boronic acid functionality offers excellent stability, ease of handling, and compatibility with diverse functional groups. Its predictable reactivity facilitates reliable synthesis of naphthalene-based heterocycles and advanced intermediates for medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      121-43-7
    • 2-Methoxynaphthalene Naproxen Impurity|CS-0229804
      93-04-9
    • ~69%
    • In-stock
      3-Methoxynaphthalene-2-boronic acid|CS-0037483
      104115-76-6

    References

    • Idemitsu Kosan Co., Ltd. Patent: EP2436679 A1, 2012 ; Location in patent: Page/Page column 51-52 ;
  • Route2
    • 2-Methoxynaphthalene Naproxen Impurity|CS-0229804
      93-04-9
    • ~85%
    • In-stock
      3-Methoxynaphthalene-2-boronic acid|CS-0037483
      104115-76-6

    References

    • Chowdhury, Sultan; Georghiou, Paris E. Journal of Organic Chemistry, 2002 , vol. 67, # 19 p. 6808 - 6811
  • Route3

    References

    • Vyskocil, Stepan; Meca, Ludek; Tislerova, Iva; Cisarova, Ivana; Polasek, Miroslav; Harutyunyan, Syuzanna R.; Belokon, Yuri N.; Stead, Russel M. J.; Farrugia, Louis; Lockhart, Stephen C.; Mitchell, William L.; Kocovsky, Pavel Chemistry--A European Journal, 2002 , vol. 8, # 20 p. 4633 - 4648

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   49.69
  • LogP   0.5282
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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