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CS-W001157 4
Total: USD 88.00

1-Bromo-3-iodo-5-nitrobenzene

  • CAS No. 861601-15-2

  • Cat. No. CS-0097730
  • Purity≥96%
  • MDL No.MFCD13194576

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

1-Bromo-3-iodo-5-nitrobenzene|CS-0097730

Structure of 861601-15-2

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General Information

  • CAS No. 861601-15-2
  • Cat. No. CS-0097730
  • Purity ≥96%
  • MDL No. MFCD13194576
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃BrINO₂
  • Molecular Weight 327.90
  • Synonym(s) 3-Bromo-5-nitroiodobenzene
  • SMILES O=[N+]([O-])C1=CC(I)=CC(Br)=C1

Description

1-Bromo-3-iodo-5-nitrobenzene features ortho-halogenated positions flanking a strong electron-withdrawing nitro group, enabling selective cross-coupling in late-stage functionalization. The bromine and iodine sites offer complementary reactivity in palladium-catalyzed transformations, facilitating sequential derivatization under mild conditions. This aryl halide exhibits excellent stability during storage and handling, making it ideal for complex molecule assembly in medicinal chemistry and materials synthesis.

Application

1-Bromo-3-iodo-5-nitrobenzene serves as a versatile dihalogenated aromatic building block for palladium-catalyzed cross-coupling reactions. The bromo and iodo substituents enable sequential functionalization, while the nitro group provides strong electron-withdrawal and ortho-directing effects. Its bench-stable nature and compatibility with standard Suzuki, Stille, and Negishi coupling conditions make it ideal for constructing complex aryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • PROLYSIS LTD. Patent: WO2007/148093 A1, 2007 ; Location in patent: Page/Page column 14-15 ; WO 2007/148093 A1
  • Route2

    References

    • Journal of the Chemical Society, , p. 783
  • Route3

    References

    • Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, , vol. <5> 22 I, p. 823 Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, , vol. <5> 23 I, p. 283 Anm.

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
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   2.9619
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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