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CS-W001157 4
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2-Bromo-1-(4-iodophenyl)ethanone

  • CAS No. 31827-94-8

  • Cat. No. CS-0186567
  • Purity≥97%
  • MDL No.None

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

2-Bromo-1-(4-iodophenyl)ethanone|CS-0186567

Structure of 31827-94-8

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General Information

  • CAS No. 31827-94-8
  • Cat. No. CS-0186567
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrIO
  • Molecular Weight 324.94
  • Synonym(s) 4-IODOPHENACYL BROMIDE
  • SMILES C1=C(C=CC(=C1)I)C(=O)CBr

Description

2-Bromo-1-(4-iodophenyl)ethanone is a halogenated aryl ketone featuring both bromo and iodo substituents on an ethanone scaffold. This dual-halogenation enables direct participation in cross-coupling reactions, particularly Suzuki-Miyaura and Stille transformations. The molecule exhibits high stability under standard bench conditions and facilitates efficient functionalization of aromatic systems.

Application

2-Bromo-1-(4-iodophenyl)ethanone serves as a versatile aryl ketone building block for palladium-catalyzed cross-coupling reactions. The bromo and iodo substituents enable sequential functionalization via Suzuki, Stille, or Negishi coupling protocols. Its bench-stable nature and compatibility with standard reaction conditions facilitate efficient construction of biaryl scaffolds and complex heterocycles in medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • CYTOKINETICS, INC. Patent: WO2007/56056 A2, 2007 ; Location in patent: Page/Page column 60; 69 ;
  • Route2
    • null|null
      186581-53-3
    • In-stock
      4-Iodobenzoic acid|CS-W014112
      619-58-9
    • ~94%
    • In-stock
      2-Bromo-1-(4-iodophenyl)ethanone|CS-0186567
      31827-94-8

    References

    • Richards, Justin J.; Melander, Christian Journal of Organic Chemistry, 2008 , vol. 73, # 13 p. 5191 - 5193
  • Route3
    • In-stock
      1-(4-Iodophenyl)ethanone|CS-W012703
      13329-40-3
    • ~71%
    • Tulobuterol Impurity 36|CS-1004188
      556110-57-7
    • In-stock
      2-Bromo-1-(4-iodophenyl)ethanone|CS-0186567
      31827-94-8

    References

    • Roman, Gheorghe; Vlahakis, Jason Z.; Vukomanovic, Dragic; Nakatsu, Kanji; Szarek, Walter A. ChemMedChem, 2010 , vol. 5, # 9 p. 1541 - 1555

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-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   2.8688
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   2

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