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2-Bromo-4-iodo-1-methylbenzene

  • CAS No. 26670-89-3

  • Cat. No. CS-W019155
  • Purity≥97%
  • MDL No.MFCD07779014

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

2-Bromo-4-iodo-1-methylbenzene|CS-W019155

Structure of 26670-89-3

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General Information

  • CAS No. 26670-89-3
  • Cat. No. CS-W019155
  • Purity ≥97%
  • MDL No. MFCD07779014
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrI
  • Molecular Weight 296.93
  • Synonym(s) Benzene, 2-bromo-4-iodo-1-methyl-
  • SMILES CC1=C(Br)C=C(I)C=C1

Description

2-Bromo-4-iodo-1-methylbenzene features a strategically positioned methyl group flanked by bromo and iodo substituents, enabling selective cross-coupling reactions. The electron-deficient aromatic ring facilitates palladium-catalyzed transformations, while the halogen pattern supports sequential functionalization. This compound serves as a key intermediate in the synthesis of complex aryl architectures.

Application

2-Bromo-4-iodo-1-methylbenzene serves as a versatile biaryl building block in cross-coupling chemistry, enabling sequential functionalization via Pd-catalyzed reactions. The ortho-bromo and para-iodo substituents provide orthogonal reactivity for iterative coupling strategies, while the methyl group enhances stability and facilitates purification. Its bench-stable nature and compatibility with standard Suzuki, Stille, and Negishi protocols make it ideal for constructing complex aromatic scaffolds in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Merck and Co., Inc. Patent: US5206235 A1, 1993 ;
  • Route2
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    • ~%
    • In-stock
      2-Bromo-4-iodo-1-methylbenzene|CS-W019155
      26670-89-3

    References

    • Varma; Sreenivasmurthyachar Journal of the Indian Chemical Society, 1936 , vol. 13, p. 187
  • Route3

    References

    • Hirtz Chemische Berichte, 1896 , vol. 29, p. 1410

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   0
  • LogP   3.36212
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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