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CS-W001157 4
Total: USD 88.00

1-Bromo-2-methoxynaphthalene

  • CAS No. 3401-47-6

  • Cat. No. CS-W004988
  • Purity≥98%
  • MDL No.MFCD00055374

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

1-Bromo-2-methoxynaphthalene|CS-W004988

Structure of 3401-47-6

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General Information

  • CAS No. 3401-47-6
  • Cat. No. CS-W004988
  • Purity ≥98%
  • MDL No. MFCD00055374
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₉BrO
  • Molecular Weight 237.10
  • Synonym(s) 2-Methoxy-1-naphtyl bromide; 1-Bromo-2-methoxynaphthalene
  • SMILES COC1=CC=C2C=CC=CC2=C1Br

Description

1-Bromo-2-methoxynaphthalene features a bromine atom at the 1-position and a methoxy group at the 2-position of the naphthalene core. This substitution pattern creates a polarized, electron-deficient aromatic system ideal for palladium-catalyzed cross-coupling reactions. The methoxy group enhances solubility while maintaining stability under standard reaction conditions.

Application

1-Bromo-2-methoxynaphthalene serves as a versatile building block in Suzuki-Miyaura and Negishi coupling reactions, enabling efficient construction of biaryl scaffolds under mild conditions. The methoxy group enhances solubility and modulates electronic properties, while the bromine substituent offers high reactivity and compatibility with palladium-catalyzed transformations. Bench-stable and readily purified by column chromatography, it functions reliably in the synthesis of functionalized naphthalene derivatives for pharmaceutical and materials applications.

Synthesis

  • Route1
    • 2-Methoxynaphthalene Naproxen Impurity|CS-0229804
      93-04-9
    • ~99%
    • In-stock
      1-Bromo-2-methoxynaphthalene|CS-W004988
      3401-47-6

    References

    • Majetich, George; Hicks, Rodgers; Reister, Steven Journal of Organic Chemistry, 1997 , vol. 62, # 13 p. 4321 - 4326
  • Route2
    • In-stock
      1-Bromonaphthalen-2-ol|CS-W007565
      573-97-7
    • null|null
      74-88-4
    • ~78%
    • In-stock
      1-Bromo-2-methoxynaphthalene|CS-W004988
      3401-47-6

    References

    • Kalgutkar, Amit S.; Kozak, Kevin R.; Crews, Brenda C.; Hochgesang Jr., G. Phillip; Marnett, Lawrence J. Journal of Medicinal Chemistry, 1998 , vol. 41, # 24 p. 4800 - 4818
  • Route3
    • In-stock
      1-Bromonaphthalen-2-ol|CS-W007565
      573-97-7
    • null|null
      77-78-1
    • ~94%
    • In-stock
      1-Bromo-2-methoxynaphthalene|CS-W004988
      3401-47-6

    References

    • Castanet, Anne-Sophie; Colobert, Francoise; Broutin, Pierre-Emmanuel; Obringer, Michel Tetrahedron Asymmetry, 2002 , vol. 13, # 6 p. 659 - 665

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   9.23
  • LogP   3.6109
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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