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CS-W001157 4
Total: USD 88.00

2,4,6-Trichloro-5-nitropyrimidine

  • CAS No. 4359-87-9

  • Cat. No. CS-W002360
  • Purity≥97%
  • MDL No.MFCD00091516

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

2,4,6-Trichloro-5-nitropyrimidine|CS-W002360

Structure of 4359-87-9

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General Information

  • CAS No. 4359-87-9
  • Cat. No. CS-W002360
  • Purity ≥97%
  • MDL No. MFCD00091516
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄Cl₃N₃O₂
  • Molecular Weight 228.42
  • Synonym(s) 2,4,6-TRICHLORO-6-NITROPYRIMIDINE
  • SMILES O=[N+](C1=C(Cl)N=C(Cl)N=C1Cl)[O-]

Description

2,4,6-Trichloro-5-nitropyrimidine serves as a key electrophilic heterocyclic scaffold for constructing advanced synthetic intermediates. The molecule features three chlorine substituents at high reactivity positions and a strongly electron-withdrawing nitro group at C5, enabling efficient coupling reactions under mild conditions. This combination delivers robust functionality in pharmaceutical and agrochemical synthesis.

Application

2,4,6-Trichloro-5-nitropyrimidine serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyrimidines via nucleophilic substitution. The trichloro and nitro groups provide orthogonal reactivity, facilitating sequential functionalization under mild conditions. Its bench-stable nature and compatibility with diverse coupling partners make it well-suited for medicinal chemistry campaigns and API intermediate development.

Synthesis

  • Route1
    • null|null
      106351-49-9
    • ~33%
    • In-stock
      2,4,6-Trichloro-5-nitropyrimidine|CS-W002360
      4359-87-9

    References

    • Zhang, Yanlei; Illarionov, Boris; Morgunova, Ekaterina; Jin, Guangyi; Bacher, Adelbert; Fischer, Markus; Ladenstein, Rudolf; Cushman, Mark Journal of Organic Chemistry, 2008 , vol. 73, # 7 p. 2715 - 2724
  • Route2
    • null|null
      106351-49-9
    • ~%
    • In-stock
      2,4,5,6-Tetrachloropyrimidine|CS-W019507
      1780-40-1
    • In-stock
      2,4,6-Trichloro-5-nitropyrimidine|CS-W002360
      4359-87-9

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2008/135785 A1, 2008 ; Location in patent: Page/Page column 63-64 ; WO 2008/135785 A1
  • Route3
    • In-stock
      5-Nitrobarbituric acid|CS-W002008
      480-68-2
    • null|null
      91-66-7
    • ~13%
    • In-stock
      2,4,6-Trichloro-5-nitropyrimidine|CS-W002360
      4359-87-9

    References

    • Dehnhardt, Christoph M.; Venkatesan, Aranapakam M.; Delos Santos, Efren; Chen, Zecheng; Santos, Osvaldo; Ayral-Kaloustian, Semiramis; Brooijmans, Natasja; Mallon, Robert; Hollander, Irwin; Feldberg, Larry; Lucas, Judy; Chaudhary, Inder; Yu, Ker; Gibbons, Jay; Abraham, Robert; Mansour, Tarek S. Journal of Medicinal Chemistry, 2010 , vol. 53, # 2 p. 798 - 810

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-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   68.92
  • LogP   2.345
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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