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CS-W001157 4
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4-Chloroquinolin-8-amine

  • CAS No. 81764-16-1

  • Cat. No. CS-W005579
  • Purity≥97%
  • MDL No.MFCD18448245

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

4-Chloroquinolin-8-amine|CS-W005579

Structure of 81764-16-1

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General Information

  • CAS No. 81764-16-1
  • Cat. No. CS-W005579
  • Purity ≥97%
  • MDL No. MFCD18448245
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇ClN₂
  • Molecular Weight 178.62
  • Synonym(s) 4-Chloro-8-aminoquinoline
  • SMILES NC1=C2N=CC=C(Cl)C2=CC=C1

Description

4-Chloroquinolin-8-amine features a quinoline core with strategically positioned chlorine and amino groups, enabling direct incorporation into bioactive molecules. The electron-deficient heterocycle pairs effectively with transition metals in cross-coupling reactions, while the amine moiety offers a handle for derivatization. This compound serves as a key building block in medicinal chemistry and materials science.

Application

4-Chloroquinolin-8-amine serves as a versatile building block in medicinal chemistry, enabling direct incorporation into quinoline-based scaffolds via palladium-catalyzed cross-coupling reactions. The chloro group facilitates efficient functionalization at C4, while the primary amine at C8 supports derivatization through acylation, alkylation, or reductive amination. Bench-stable and compatible with standard purification methods, it functions reliably in the synthesis of kinase inhibitors and other bioactive heterocycles.

Synthesis

  • Route1

    References

    • Zhang, Yu; Guo, Xiangfeng; Jia, Lihua; Xu, Shicheng; Xu, Zhihui; Zheng, Libo; Qian, Xuhong Dalton Transactions, 2012 , vol. 41, # 38 p. 11776 - 11782
  • Route2
    • null|null
      75698-26-9
    • ~0%
    • null|null
      75698-27-0
    • In-stock
      4-Chloroquinolin-8-amine|CS-W005579
      81764-16-1

    References

    • Semenov, V. P.; Studenikov, A. N. Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980 , vol. 16, # 7 p. 754 - 757 Khimiya Geterotsiklicheskikh Soedinenii, 1980 , # 7 p. 972 - 975
  • Route3

    References

    • Gouley et al. Journal of the American Chemical Society, 1947 , vol. 69, p. 303,306

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   2.4704
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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