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CS-W001157 4
Total: USD 88.00

6-bromoisoquinolin-3-amine

  • CAS No. 891785-28-7

  • Cat. No. CS-W001039
  • Purity≥96%
  • MDL No.MFCD11101002

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

6-bromoisoquinolin-3-amine|CS-W001039

Structure of 891785-28-7

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General Information

  • CAS No. 891785-28-7
  • Cat. No. CS-W001039
  • Purity ≥96%
  • MDL No. MFCD11101002
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇BrN₂
  • Molecular Weight 223.07
  • Synonym(s) 6-Bromoisoquinolin-3-amine, 3-Amino-6-bromo-2-azanaphthalene
  • SMILES Nc1cc2cc(Br)ccc2cn1

Description

6-Bromoisoquinolin-3-amine features a brominated isoquinoline core with a strategically positioned amine group, enabling direct functionalization in cross-coupling and C–H amination reactions. This electron-deficient heterocycle delivers high reactivity under palladium catalysis, facilitating efficient access to complex pharmaceutical intermediates. The bromo substituent serves as a reliable handle for further diversification, while the amine moiety enhances solubility and binding affinity in target-directed synthesis.

Application

6-Bromoisoquinolin-3-amine serves as a versatile building block for the synthesis of isoquinoline-based pharmaceuticals and functional materials. The bromine at the 6-position enables palladium-catalyzed cross-coupling reactions, while the primary amine at the 3-position offers a handle for derivatization via acylation, alkylation, or reductive amination. Its bench-stable solid form facilitates handling and purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1
    • 1,6-Dibromoisoquinolin-3-amine|CS-0187889
      925672-85-1
    • ~88%
    • In-stock
      6-bromoisoquinolin-3-amine|CS-W001039
      891785-28-7

    References

    • AMGEN INC. Patent: WO2009/11880 A2, 2009 ; Location in patent: Page/Page column 159-160 ; WO 2009/011880 A2
  • Route2
    • null|null
      956100-48-4
    • ~%
    • In-stock
      6-bromoisoquinolin-3-amine|CS-W001039
      891785-28-7

    References

    • WO2007/125405 A2, ; Page/Page column 17; 36 ; WO 2007/125405 A2
  • Route3
    • null|null
      934343-53-0
    • ~66%
    • In-stock
      6-bromoisoquinolin-3-amine|CS-W001039
      891785-28-7

    References

    • Zhu, Gui-Dong; Gong, Jianchun; Claiborne, Akiyo; Woods, Keith W.; Gandhi, Viraj B.; Thomas, Sheela; Luo, Yan; Liu, Xuesong; Shi, Yan; Guan, Ran; Magnone, Shayna R.; Klinghofer, Vered; Johnson, Eric F.; Bouska, Jennifer; Shoemaker, Alexander; Oleksijew, Anatol; Stoll, Vincent S.; Jong, Ron De; Oltersdorf, Tilman; Li, Qun; Rosenberg, Saul H.; Giranda, Vincent L. Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 12 p. 3150 - 3155

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   38.91
  • LogP   2.5795
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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