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CS-W001157 4
Total: USD 88.00

5-Chloroquinoline

  • CAS No. 635-27-8

  • Cat. No. CS-W002581
  • Purity≥97%
  • MDL No.MFCD00239413

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

5-Chloroquinoline|CS-W002581

Structure of 635-27-8

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General Information

  • CAS No. 635-27-8
  • Cat. No. CS-W002581
  • Purity ≥97%
  • MDL No. MFCD00239413
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆ClN
  • Molecular Weight 163.60
  • Synonym(s) None
  • SMILES Clc1cccc2c1cccn2

Description

5-Chloroquinoline is a heterocyclic compound featuring a chlorine atom at the 5-position of the quinoline core. This electron-deficient scaffold serves as a key building block in medicinal chemistry, enabling direct incorporation into bioactive molecules through cross-coupling reactions. The chloro group enhances reactivity in palladium-catalyzed transformations and contributes to favorable pharmacokinetic properties in drug candidates.

Application

5-Chloroquinoline serves as a versatile building block in medicinal chemistry and synthetic organic chemistry, enabling direct functionalization at the C5 position via palladium-catalyzed cross-coupling reactions. Its electron-deficient aromatic core enhances reactivity in nucleophilic substitution processes, while maintaining bench stability and compatibility with common protecting groups. The molecule functions effectively in the synthesis of quinoline-based pharmaceuticals, agrochemicals, and ligands for transition metal catalysis.

Synthesis

  • Route1

    References

    • Karramkam, Mylene; Dolle, Frederic; Valette, Heric; Besret, Laurent; Bramoulle, Yann; Hinnen, Francoise; Vaufrey, Francoise; Franklin, Carine; Bourg, Sebastien; Coulon, Christine; Ottaviani, Michele; Delaforge, Marcel; Loc'h, Christian; Bottlaender, Michel; Crouzel, Christian Bioorganic and medicinal chemistry, 2002 , vol. 10, # 8 p. 2611 - 2623
  • Route2

    References

    • Journal fuer Praktische Chemie (Leipzig), , vol. <2> 48, p. 263 Journal fuer Praktische Chemie (Leipzig), , vol. <2> 48, p. 283 Chemische Berichte, , vol. 18, p. 2941 Chemische Berichte, , vol. 17, p. 927
  • Route3
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      124-40-3
    • ~%
    • In-stock
      5-Chloroquinoline|CS-W002581
      635-27-8
    • null|null
      14252-23-4

    References

    • Journal of the Chemical Society, , p. 441,443

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   12.89
  • LogP   2.8882
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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