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1-(2,4-Dinitrophenyl)pyridin-1-ium chloride

  • CAS No. 4185-69-7

  • Cat. No. CS-0179394
  • Molecule weight281.65
  • Purity≥97%
  • MDL No.None

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

1-(2,4-Dinitrophenyl)pyridin-1-ium chloride|CS-0179394

Structure of 4185-69-7

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General Information

  • CAS No. 4185-69-7
  • Cat. No. CS-0179394
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈ClN₃O₄
  • Molecular Weight 281.65
  • Synonym(s) Zincke Salt
  • SMILES O=[N+](C1=CC=C([N+]2=CC=CC=C2)C([N+]([O-])=O)=C1)[O-].[Cl-]

Description

1-(2,4-Dinitrophenyl)pyridin-1-ium chloride features a pyridinium core flanked by electron-deficient dinitrophenyl and chloride counterion, enabling strong electrophilic character. This structure facilitates efficient coupling reactions in synthetic organic chemistry, particularly in nucleophilic substitution protocols. The compound exhibits high reactivity under mild conditions and maintains stability during storage.

Application

1-(2,4-Dinitrophenyl)pyridin-1-ium chloride serves as a versatile electrophilic reagent in synthetic organic chemistry, enabling efficient C–H functionalization and arylation reactions under mild conditions. Its pyridinium core exhibits enhanced stability and solubility in polar solvents, facilitating straightforward purification and handling. The 2,4-dinitrophenyl group provides strong electron-withdrawing character, promoting reactivity in nucleophilic substitution and transition-metal-catalyzed coupling processes. This compound functions reliably as a building block for heterocyclic scaffolds and conjugated systems in medicinal chemistry applications.

Synthesis

  • Route1
    • null|null
      97-00-7
    • ~68%
    • In-stock
      1-(2,4-Dinitrophenyl)pyridin-1-ium chloride|CS-0179394
      4185-69-7

    References

    • Polaroid Corporation Patent: US5262549 A1, 1993 ;
  • Route2
    • null|null
      110-86-1
    • null|null
      97-00-7
    • ~99%
    • In-stock
      1-(2,4-Dinitrophenyl)pyridin-1-ium chloride|CS-0179394
      4185-69-7

    References

    • Michels, Theo D.; Rhee, Jong Uk; Vanderwal, Christopher D. Organic Letters, 2008 , vol. 10, # 21 p. 4787 - 4790
  • Route3
    • null|null
      53405-99-5
    • ~%
    • In-stock
      1-(2,4-Dinitrophenyl)pyridin-1-ium chloride|CS-0179394
      4185-69-7

    References

    • Zincke; Heuser; Moeller Justus Liebigs Annalen der Chemie, 1904 , vol. 333, p. 338 Full Text Show Details Zincke Justus Liebigs Annalen der Chemie, 1904 , vol. 330, p. 367 Justus Liebigs Annalen der Chemie, 1904 , vol. 333, p. 340

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

Quality Control

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Computational Chemistry Data

  • TPSA   90.16
  • LogP   -1.2163
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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