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CS-W001157 4
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1,3-Dibromoisoquinoline

  • CAS No. 53987-60-3

  • Cat. No. CS-W021278
  • Purity≥97%
  • MDL No.MFCD00234474

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

1,3-Dibromoisoquinoline|CS-W021278

Structure of 53987-60-3

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General Information

  • CAS No. 53987-60-3
  • Cat. No. CS-W021278
  • Purity ≥97%
  • MDL No. MFCD00234474
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅Br₂N
  • Molecular Weight 286.95
  • Synonym(s) isoquinoline,1,3-dibromo
  • SMILES BrC1=NC(=CC2=CC=CC=C12)Br

Description

1,3-Dibromoisoquinoline features two bromine atoms positioned at the 1 and 3 ring junctions of the isoquinoline core, conferring enhanced electrophilicity and enabling selective functionalization in cross-coupling reactions. This sterically accessible scaffold integrates readily into complex heterocyclic architectures under mild conditions.

Application

1,3-Dibromoisoquinoline serves as a versatile building block in synthetic organic chemistry, enabling regioselective functionalization at the 1- and 3-positions of the isoquinoline core. Its dual bromine substituents facilitate palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, with high efficiency and functional group tolerance. The compound exhibits good bench stability and ease of purification, making it well-suited for iterative synthesis of complex heterocyclic scaffolds relevant to medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Eisai Co., Ltd. Patent: US6340759 B1, 2002 ; Location in patent: Example 28 ;
  • Route2
    • null|null
      86-94-2
    • ~48%
    • In-stock
      1,3-Dibromoisoquinoline|CS-W021278
      53987-60-3

    References

    • Hirschhaeuser, Christoph; Haseler, Claire A.; Gallagher, Timothy Angewandte Chemie - International Edition, 2011 , vol. 50, # 22 p. 5162 - 5165
  • Route3

    References

    • WO2012/41476 A1, ; WO 2012/041476 A1

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   12.89
  • LogP   3.7598
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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