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2-Chloro-8-nitroquinoline

  • CAS No. 4225-86-9

  • Cat. No. CS-0155824
  • Purity≥97%
  • MDL No.MFCD00160589

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

2-Chloro-8-nitroquinoline|CS-0155824

Structure of 4225-86-9

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General Information

  • CAS No. 4225-86-9
  • Cat. No. CS-0155824
  • Purity ≥97%
  • MDL No. MFCD00160589
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅ClN₂O₂
  • Molecular Weight 208.60
  • Synonym(s) 2-Chloro-8-nitro-quinoline
  • SMILES C1=CC2=C(C(=C1)[N+](=O)[O-])N=C(C=C2)Cl

Description

2-Chloro-8-nitroquinoline is a nitrogen-containing heterocyclic compound featuring a chlorine substituent at the 2-position and a nitro group at the 8-position. This electron-deficient quinoline scaffold enables direct functionalization in cross-coupling reactions and serves as a key building block for advanced pharmaceutical intermediates and fluorescent probes.

Application

2-Chloro-8-nitroquinoline serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. Its electron-deficient quinoline core exhibits enhanced reactivity at the C2 position, while the nitro group provides a handle for reduction and subsequent cyclization. The compound demonstrates excellent bench stability and compatibility with common protecting groups, facilitating modular synthesis of complex heterocyclic scaffolds.

Synthesis

  • Route1

    References

    • MEMORY PHARMACEUTICALS CORPORATION; SCHUMACHER, Richard, A.; TEHIM, Ashok; XIE, Wenge Patent: WO2010/24980 A1, 2010 ; Location in patent: Page/Page column 93; 94 ;
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    References

    • Paloque, Lucie; Verhaeghe, Pierre; Casanova, Magali; Castera-Ducros, Caroline; Dumetre, Aurelien; Mbatchi, Litaty; Hutter, Sebastien; Kraiem-M'Rabet, Manel; Laget, Michele; Remusat, Vincent; Rault, Sylvain; Rathelot, Pascal; Azas, Nadine; Vanelle, Patrice European Journal of Medicinal Chemistry, 2012 , vol. 54, p. 75 - 86
  • Route3
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    • In-stock
      2-Chloro-8-nitroquinoline|CS-0155824
      4225-86-9

    References

    • Ochiai et al. Yakugaku Zasshi, 1943 , vol. 63, p. 280 Chem.Abstr., 1951 , p. 5152

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

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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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