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CS-W001157 4
Total: USD 88.00

2-Bromo-1-iodo-3-methoxybenzene

  • CAS No. 74128-84-0

  • Cat. No. CS-0100432
  • Purity≥97%
  • MDL No.MFCD18391616

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

2-Bromo-1-iodo-3-methoxybenzene|CS-0100432

Structure of 74128-84-0

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General Information

  • CAS No. 74128-84-0
  • Cat. No. CS-0100432
  • Purity ≥97%
  • MDL No. MFCD18391616
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrIO
  • Molecular Weight 312.93
  • Synonym(s) 2-Bromo-3-iodoanisole
  • SMILES COC1=C(Br)C(I)=CC=C1

Description

2-Bromo-1-iodo-3-methoxybenzene features a strategically positioned methoxy group that enhances solubility and directs electrophilic substitution. The orthogonal halogenation pattern enables sequential cross-coupling reactions, while the bench-stable aryl iodide serves as a reliable coupling partner in palladium-catalyzed transformations.

Application

2-Bromo-1-iodo-3-methoxybenzene serves as a versatile dihalogenated aromatic building block for palladium-catalyzed cross-coupling reactions. The ortho-bromine and meta-iodine substituents enable sequential functionalization with high chemoselectivity, while the methoxy group provides moderate electron donation and enhances solubility. This compound exhibits excellent bench stability and facilitates efficient purification, making it well-suited for the construction of complex substituted arenes in medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1
    • In-stock
      2-Bromo-3-iodophenol|CS-0088155
      863870-88-6
    • null|null
      74-88-4
    • ~97%
    • In-stock
      2-Bromo-1-iodo-3-methoxybenzene|CS-0100432
      74128-84-0

    References

    • Tadd, Andrew C.; Fielding, Mark R.; Willis, Michael C. Chemical Communications, 2009 , # 44 p. 6744 - 6746
  • Route2

    References

    • Ooi, Takashi; Takahashi, Makoto; Yamada, Masao; Tayama, Eiji; Omoto, Kiyoyuki; Maruoka, Keiji Journal of the American Chemical Society, 2004 , vol. 126, # 4 p. 1150 - 1160
  • Route3

    References

    • Ooi, Takashi; Takahashi, Makoto; Yamada, Masao; Tayama, Eiji; Omoto, Kiyoyuki; Maruoka, Keiji Journal of the American Chemical Society, 2004 , vol. 126, # 4 p. 1150 - 1160

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-H332-H335
Precautionary Statements : P233-P260-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   3.0623
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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