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Ethyl 4,6-dichloroquinoline-3-carboxylate

  • CAS No. 21168-41-2

  • Cat. No. CS-0097494
  • Purity≥98%
  • MDL No.MFCD00173348

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

Ethyl 4,6-dichloroquinoline-3-carboxylate|CS-0097494

Structure of 21168-41-2

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General Information

  • CAS No. 21168-41-2
  • Cat. No. CS-0097494
  • Purity ≥98%
  • MDL No. MFCD00173348
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₉Cl₂NO₂
  • Molecular Weight 270.11
  • Synonym(s) 3-Quinolinecarboxylic acid, 4,6-dichloro-, ethyl ester
  • SMILES O=C(C1=C(Cl)C2=CC(Cl)=CC=C2N=C1)OCC

Description

Ethyl 4,6-dichloroquinoline-3-carboxylate features a rigid quinoline core with strategically positioned chloro substituents at the 4- and 6-positions, enhancing electron deficiency for electrophilic substitution. The ester functionality enables facile derivatization in transition metal-catalyzed coupling reactions. This bench-stable reagent serves as a key intermediate in synthesizing bioactive quinoline-based pharmaceuticals and functional materials.

Application

Ethyl 4,6-dichloroquinoline-3-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted quinoline scaffolds. The dichloro substitution pattern facilitates regioselective palladium-catalyzed cross-coupling reactions, while the ester functionality supports subsequent transformations including hydrolysis and amidation. Bench-stable and readily purified by column chromatography, it functions as a key intermediate in the construction of bioactive molecules and pharmaceutical candidates requiring functionalized quinoline cores.

Synthesis

  • Route1

    References

    • Journal of Medicinal Chemistry, , vol. 55, # 7 p. 3578 - 3582
  • Route2
    • Ethyl 6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate|CS-1639034
      79607-22-0
    • ~%
    • In-stock
      Ethyl 4,6-dichloroquinoline-3-carboxylate|CS-0097494
      21168-41-2

    References

    • WO2010/44885 A2, ; Page/Page column 79-81 ;
  • Route3

    References

    • Farmaco, , vol. 53, # 8-9 p. 579 - 585

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
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   39.19
  • LogP   3.7183
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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