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CS-W001157 4
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Methyl 5-bromo-2-iodobenzoate

  • CAS No. 181765-86-6

  • Cat. No. CS-W018330
  • Purity≥96%
  • MDL No.MFCD00144771

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

Methyl 5-bromo-2-iodobenzoate|CS-W018330

Structure of 181765-86-6

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General Information

  • CAS No. 181765-86-6
  • Cat. No. CS-W018330
  • Purity ≥96%
  • MDL No. MFCD00144771
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrIO₂
  • Molecular Weight 340.94
  • Synonym(s) 5-Bromo-2-iodobenzoic Acid Methyl Ester
  • SMILES COC(=O)C1=C(I)C=CC(Br)=C1

Description

Methyl 5-bromo-2-iodobenzoate features a dual halogenated aromatic core, enabling efficient cross-coupling reactions in synthetic organic chemistry. The bromo and iodo substituents occupy meta and ortho positions relative to the ester group, offering orthogonal reactivity for sequential functionalization. This configuration supports palladium-catalyzed transformations with high chemoselectivity. The compound exhibits bench-stable handling under standard conditions.

Application

Methyl 5-bromo-2-iodobenzoate serves as a versatile dihalogenated aromatic building block for palladium-catalyzed cross-coupling reactions. The ortho-bromo and meta-iodo substituents enable sequential functionalization, facilitating the construction of complex biaryl systems and heterocyclic scaffolds. Its bench-stable nature and compatibility with standard coupling conditions make it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • US2004/92521 A1, ; Page/Page column 16-20; 46 ; US 20040092521 A1
  • Route2
    • null|null
      67-56-1
    • In-stock
      5-Bromo-2-iodobenzoic acid|CS-W002338
      21740-00-1
    • ~95%
    • In-stock
      Methyl 5-bromo-2-iodobenzoate|CS-W018330
      181765-86-6

    References

    • Organic Letters, , vol. 10, # 14 p. 3001 - 3004
  • Route3

    References

    • Journal of the Chemical Society, , vol. 78, p. 6130,6134

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   2.8403
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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