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CS-W001157 4
Total: USD 88.00

5-Bromo-2-iodoanisole

  • CAS No. 791642-68-7

  • Cat. No. CS-W020552
  • Purity≥97%
  • MDL No.MFCD11847482

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

5-Bromo-2-iodoanisole|CS-W020552

Structure of 791642-68-7

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General Information

  • CAS No. 791642-68-7
  • Cat. No. CS-W020552
  • Purity ≥97%
  • MDL No. MFCD11847482
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrIO
  • Molecular Weight 312.93
  • Synonym(s) 5-Bromo-2-iodoanisole; 4-Bromo-1-iodo-2-methoxybenzene
  • SMILES COC1=CC(Br)=CC=C1I

Description

5-Bromo-2-iodoanisole features a strategically positioned bromo and iodo substituent on an aromatic ring, enabling selective cross-coupling reactions. The methoxy group enhances solubility and directs regiochemistry, while the halogen pairs offer orthogonal reactivity for sequential transformations in complex molecule assembly.

Application

5-Bromo-2-iodoanisole serves as a versatile diaryl building block for palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl scaffolds. The bromo and iodo substituents offer orthogonal reactivity in sequential coupling processes, while the methoxy group provides electronic modulation and enhanced solubility. Bench-stable and readily purified by flash chromatography, it functions reliably in Suzuki, Stille, and Negishi couplings, supporting scalable synthesis of functionalized heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Ochi, Takanori; Yamaguchi, Yoshihiro; Wakamiya, Tateaki; Matsubara, Yoshio; Yoshida, Zen-Ichi Organic and Biomolecular Chemistry, 2008 , vol. 6, # 7 p. 1222 - 1231
  • Route2
    • N-(2-Methoxy-4-nitrophenyl)acetamide|CS-0187539
      93-27-6
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    • In-stock
      5-Bromo-2-iodoanisole|CS-W020552
      791642-68-7

    References

    • Journal of the American Chemical Society, , vol. 57, p. 1592,1594
  • Route3
    • N-(4-Amino-2-methoxyphenyl)acetamide|CS-0666903
      5329-15-7
    • ~%
    • In-stock
      5-Bromo-2-iodoanisole|CS-W020552
      791642-68-7

    References

    • Journal of the American Chemical Society, , vol. 57, p. 1592,1594

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   3.0623
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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