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CS-W001157 4
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2-Chloroquinoline-6-carbonitrile

  • CAS No. 78060-54-5

  • Cat. No. CS-0136555
  • Purity≥97%
  • MDL No.MFCD09038087

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

2-Chloroquinoline-6-carbonitrile|CS-0136555

Structure of 78060-54-5

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General Information

  • CAS No. 78060-54-5
  • Cat. No. CS-0136555
  • Purity ≥97%
  • MDL No. MFCD09038087
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₅ClN₂
  • Molecular Weight 188.61
  • Synonym(s) 2-Chloro-6-quinolinecarbonitrile
  • SMILES N#CC1=CC=C2N=C(Cl)C=CC2=C1

Description

2-Chloroquinoline-6-carbonitrile features a quinoline scaffold with strategically positioned chlorine and nitrile groups, enabling efficient integration into pharmaceutical and agrochemical scaffolds. The electron-deficient ring system facilitates coupling reactions, while the nitrile moiety offers versatility in downstream functionalization. This compound exhibits robust stability under standard conditions and serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and bioactive heterocycles.

Application

2-Chloroquinoline-6-carbonitrile serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the 2-position via palladium-catalyzed cross-coupling. Its electron-deficient quinoline core and orthogonal nitrile group facilitate selective transformations, while the chloro substituent supports further derivatization through nucleophilic substitution or metal-catalyzed coupling. The compound exhibits good bench stability and is readily purified by flash chromatography, making it well-suited for scalable synthesis of kinase inhibitors and other bioactive heterocycles.

Synthesis

  • Route1
    • KLK7-IN-1|CS-0668863
      63124-11-8
    • ~79%
    • In-stock
      2-Chloroquinoline-6-carbonitrile|CS-0136555
      78060-54-5

    References

    • Zaragoza, Florencio; Stephensen, Henrik; Peschke, Bernd; Rimvall, Karin Journal of Medicinal Chemistry, 2005 , vol. 48, # 1 p. 306 - 311
  • Route2

    References

    • Zaragoza, Florencio; Stephensen, Henrik; Peschke, Bernd; Rimvall, Karin Journal of Medicinal Chemistry, 2005 , vol. 48, # 1 p. 306 - 311
  • Route3
    • (E)-N-(4-bromophenyl)-3-ethoxyacrylamide|CS-0451061
      327058-51-5
    • ~%
    • In-stock
      2-Chloroquinoline-6-carbonitrile|CS-0136555
      78060-54-5

    References

    • Zaragoza, Florencio; Stephensen, Henrik; Peschke, Bernd; Rimvall, Karin Journal of Medicinal Chemistry, 2005 , vol. 48, # 1 p. 306 - 311

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   36.68
  • LogP   2.75988
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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