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CS-W001157 4
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1,2-Dibromo-3-methoxybenzene

  • CAS No. 95970-22-2

  • Cat. No. CS-0040072
  • Purity≥98%
  • MDL No.MFCD09864854

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

1,2-Dibromo-3-methoxybenzene|CS-0040072

Structure of 95970-22-2

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General Information

  • CAS No. 95970-22-2
  • Cat. No. CS-0040072
  • Purity ≥98%
  • MDL No. MFCD09864854
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆Br₂O
  • Molecular Weight 265.93
  • Synonym(s) 2,3-Dibromoanisole
  • SMILES COC1=C(Br)C(Br)=CC=C1

Description

1,2-Dibromo-3-methoxybenzene features a methoxy group positioned ortho to two bromine substituents, creating a uniquely activated aromatic scaffold. This configuration enables selective cross-coupling reactions under palladium catalysis, where the electron-donating methoxy group stabilizes intermediates and directs regioselective functionalization. The compound exhibits bench-stable handling characteristics and integrates efficiently into complex molecular architectures requiring dual halogenation sites.

Application

1,2-Dibromo-3-methoxybenzene serves as a versatile ortho-dibrominated aromatic building block for palladium-catalyzed cross-coupling reactions. The methoxy group provides moderate electron donation and enhances solubility, while the bromine atoms enable sequential functionalization under standard Suzuki, Stille, or Negishi conditions. Bench-stable and readily purified by column chromatography, it functions reliably in the synthesis of complex biaryl architectures and substituted heterocycles.

Synthesis

  • Route1
    • In-stock
      1,2-Dibromo-3-fluorobenzene|CS-0038046
      811711-33-8
    • null|null
      67-56-1
    • ~58%
    • In-stock
      1,2-Dibromo-3-methoxybenzene|CS-0040072
      95970-22-2

    References

    • Menzel, Karsten; Dimichele, Lisa; Mills, Paul; Frantz, Doug E.; Nelson, Todd D.; Kress, Michael H. Synlett, 2006 , # 12 p. 1948 - 1952
  • Route2
    • null|null
      2398-37-0
    • ~1%
    • null|null
      95970-10-8
    • In-stock
      1,2-Dibromo-4-methoxybenzene|CS-0106499
      62415-74-1
    • In-stock
      1,2-Dibromo-3-methoxybenzene|CS-0040072
      95970-22-2

    References

    • Castellonese, Paul; Villa, Pierre Helvetica Chimica Acta, 1983 , vol. 66, # 4 p. 1068 - 1077
  • Route3
    • In-stock
      1,2-Dibromo-3-fluorobenzene|CS-0038046
      811711-33-8
    • null|null
      124-41-4
    • ~65%
    • In-stock
      1,2-Dibromo-3-methoxybenzene|CS-0040072
      95970-22-2

    References

    • Diemer, Vincent; Leroux, Frederic R.; Colobert, Fracoise European Journal of Organic Chemistry, 2011 , # 2 p. 327 - 340

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335-H413
Precautionary Statements : P261-P264-P271-P273-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   3.2202
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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