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Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

  • CAS No. 98349-25-8

  • Cat. No. CS-0151710
  • Molecule weight293.27
  • Purity≥98%
  • MDL No.MFCD01646378

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

Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate|CS-0151710

Structure of 98349-25-8

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General Information

  • CAS No. 98349-25-8
  • Cat. No. CS-0151710
  • Purity ≥98%
  • MDL No. MFCD01646378
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₃F₂NO₃
  • Molecular Weight 293.27
  • Synonym(s) Ethyl 1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate
  • SMILES CCOC(=O)C1=CN(C2CC2)C3=CC(=C(C=C3C1=O)F)F

Description

Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate is a bench-stable, moisture-tolerant quinolone core featuring electron-deficient fluorine substituents at C6 and C7. This structural motif enables direct incorporation into synthetic routes for fluoroquinolone antibiotics, offering enhanced metabolic stability and improved membrane permeability.

Application

Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate serves as a key intermediate in the synthesis of fluoroquinolone-based scaffolds. Its difluorinated quinoline core enables enhanced metabolic stability and membrane penetration, while the ethyl ester group facilitates downstream functionalization via hydrolysis or coupling reactions. The cyclopropyl substitution at N1 provides steric and electronic tuning beneficial for antibiotic potency. Bench-stable and readily purified by flash chromatography, it functions reliably in standard synthetic workflows targeting bioactive heterocycles.

Synthesis

  • Route1
    • null|null
      101799-76-2
    • ~84%
    • In-stock
      Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate|CS-0151710
      98349-25-8

    References

    • Grohe, Klaus; Heitzer, Helmut Liebigs Annalen der Chemie, 1987 , p. 29 - 37
  • Route2
    • null|null
      138998-46-6
    • null|null
      765-30-0
    • ~97%
    • In-stock
      Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate|CS-0151710
      98349-25-8

    References

    • GLAXO GROUP LIMITED; SHIONOGI and CO., LTD.; LIAO, Xiangmin; PEARSON, Neil, David; PENDRAK, Israil; SANO, Masayuki Patent: WO2013/52568 A1, 2013 ; Location in patent: Page/Page column 200; 201 ;
  • Route3
    • null|null
      110600-97-0
    • ~30%
    • In-stock
      Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate|CS-0151710
      98349-25-8

    References

    • Egawa; Kataoka; Shibamori; et al. Journal of Heterocyclic Chemistry, 1987 , vol. 24, # 1 p. 181 - 185

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   48.3
  • LogP   2.7913
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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