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CS-W001157 4
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5-Chloro-8-nitroquinoline

  • CAS No. 6942-98-9

  • Cat. No. CS-0155794
  • Purity≥96%
  • MDL No.MFCD00552691

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

5-Chloro-8-nitroquinoline|CS-0155794

Structure of 6942-98-9

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General Information

  • CAS No. 6942-98-9
  • Cat. No. CS-0155794
  • Purity ≥96%
  • MDL No. MFCD00552691
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅ClN₂O₂
  • Molecular Weight 208.60
  • Synonym(s) NSC 51628
  • SMILES C1=CC2=C(C(=CC=C2Cl)[N+](=O)[O-])N=C1

Description

5-Chloro-8-nitroquinoline is a nitrogen-rich heterocyclic compound featuring a chloro group at the 5-position and a nitro moiety at the 8-position, conferring strong electron-withdrawing character. This scaffold enables direct integration into advanced synthetic routes for pharmaceutical intermediates and functional materials, offering enhanced reactivity in cross-coupling and electrophilic substitution processes under standard conditions.

Application

5-Chloro-8-nitroquinoline serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the quinoline core through palladium-catalyzed cross-coupling reactions. Its electron-deficient nature enhances reactivity in nucleophilic substitution processes, while the ortho-chloro and nitro groups provide orthogonal handles for sequential derivatization. The compound exhibits excellent bench stability and facilitates efficient purification via crystallization, supporting scalable synthesis of advanced heterocyclic scaffolds.

Synthesis

  • Route1

    References

    • NOSCIRA, S.A.; MEDINA PADILLA, Miguel; CASTRO MORERA, Ana; SANCHEZ-QUESADA, Jorge; GARCIA PALOMERO, Esther Patent: WO2010/66832 A1, 2010 ; Location in patent: Page/Page column 30-31 ;
  • Route2
    • N-(5-Chloro-2-nitrophenyl)acetamide|CS-W014920
      5443-33-4
    • ~%
    • In-stock
      5-Chloro-8-nitroquinoline|CS-0155794
      6942-98-9

    References

    • Bulletin de la Societe Chimique de France, , vol. <4> 47, p. 749
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 76, p. 6089,6092

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-P338-P351-P362-P405-P501

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Computational Chemistry Data

  • TPSA   56.03
  • LogP   2.7964
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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