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CS-W001157 4
Total: USD 88.00

1,3-Dibromo-2-iodobenzene

  • CAS No. 19821-80-8

  • Cat. No. CS-0029671
  • Purity≥98%
  • MDL No.MFCD00192666

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

1,3-Dibromo-2-iodobenzene|CS-0029671

Structure of 19821-80-8

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General Information

  • CAS No. 19821-80-8
  • Cat. No. CS-0029671
  • Purity ≥98%
  • MDL No. MFCD00192666
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃Br₂I
  • Molecular Weight 361.80
  • Synonym(s) 3-dibroMo-2-iodobenzene
  • SMILES IC1=C(Br)C=CC=C1Br

Description

1,3-Dibromo-2-iodobenzene features a uniquely substituted benzene ring bearing bromo and iodo groups at adjacent positions, enabling selective cross-coupling reactions. This trihalogenated aromatic scaffold offers enhanced reactivity in palladium-catalyzed transformations, where the distinct halogen reactivities facilitate sequential functionalization. The molecule's stability under standard conditions supports reliable handling in synthetic workflows.

Application

1,3-Dibromo-2-iodobenzene serves as a versatile ortho-halogenated aromatic building block for palladium-catalyzed cross-coupling reactions. Its complementary halogen pattern enables sequential functionalization via Suzuki, Stille, or Negishi coupling protocols. The compound exhibits excellent bench stability and facilitates the construction of complex biaryl scaffolds with high regiocontrol, making it valuable in medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1

    References

    • Leroux, Frederic R.; Bonnafoux, Laurence; Heiss, Christophe; Colobert, Francoise; Lanfranchi, Don Antoine Advanced Synthesis and Catalysis, 2007 , vol. 349, # 17-18 p. 2705 - 2713
  • Route2

    References

    • Mao, Guoliang; Orita, Akihiro; Matsuo, Daisuke; Hirate, Takayoshi; Iwanaga, Tetsuo; Toyota, Shinji; Otera, Junzo Tetrahedron Letters, 2009 , vol. 50, # 24 p. 2860 - 2864
  • Route3
    • null|null
      401631-86-5
    • ~80%
    • In-stock
      1,3-Dibromobenzene|CS-W008980
      108-36-1
    • In-stock
      1,3-Dibromo-2-iodobenzene|CS-0029671
      19821-80-8

    References

    • Barbero; Degani; Diulgheroff; Dughera; Fochi Synthesis, 2001 , # 14 p. 2180 - 2190

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

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.8162
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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