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CS-W001157 4
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2-Bromo-1-methoxynaphthalene

  • CAS No. 62012-54-8

  • Cat. No. CS-0041682
  • Purity≥95%
  • MDL No.None

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

2-Bromo-1-methoxynaphthalene|CS-0041682

Structure of 62012-54-8

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General Information

  • CAS No. 62012-54-8
  • Cat. No. CS-0041682
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₉BrO
  • Molecular Weight 237.09
  • Synonym(s) None
  • SMILES COC1=C2C=CC=CC2=CC=C1Br

Description

2-Bromo-1-methoxynaphthalene features a bromine atom at the 2-position and a methoxy group at the 1-position of the naphthalene core, creating a dual-functionalized scaffold. This arrangement enables selective coupling reactions in transition-metal-catalyzed transformations, particularly Suzuki-Miyaura and Stille couplings. The electron-withdrawing bromide and electron-donating methoxy substituents establish a polarized system ideal for directed functionalization. Bench-stable under standard conditions, it facilitates reliable incorporation into complex molecular architectures without significant decomposition.

Application

2-Bromo-1-methoxynaphthalene serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl scaffolds. The bromine atom exhibits high reactivity in Pd-catalyzed coupling processes, while the methoxy group provides ortho-directing capability and enhanced solubility. This compound demonstrates excellent bench stability and compatibility with diverse functional groups, facilitating straightforward purification and integration into complex molecule synthesis.

Synthesis

  • Route1

    References

    • Synthetic Communications, , vol. 32, # 15 p. 2313 - 2318
  • Route2
    • null|null
      186581-53-3
    • In-stock
      2-Bromonaphthalen-1-ol|CS-W005491
      771-15-3
    • ~%
    • In-stock
      2-Bromo-1-methoxynaphthalene|CS-0041682
      62012-54-8

    References

    • Chemische Berichte, , vol. 90, p. 1537,1541
  • Route3
    • In-stock
      2-Bromonaphthalen-1-ol|CS-W005491
      771-15-3
    • null|null
      74-88-4
    • ~81%
    • In-stock
      2-Bromo-1-methoxynaphthalene|CS-0041682
      62012-54-8

    References

    • Mazzanti, Andrea; Chiarucci, Michel; Bentley, Keith W.; Wolf, Christian Journal of Organic Chemistry, 2014 , vol. 79, # 8 p. 3725 - 3730

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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