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CS-W001157 4
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4,6-Dichloro-2-phenylpyrimidine

  • CAS No. 3740-92-9

  • Cat. No. CS-W013048
  • Molecule weight225.08
  • Purity≥97%
  • MDL No.MFCD00754193

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

4,6-Dichloro-2-phenylpyrimidine|CS-W013048

Structure of 3740-92-9

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General Information

  • CAS No. 3740-92-9
  • Cat. No. CS-W013048
  • Purity ≥97%
  • MDL No. MFCD00754193
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆Cl₂N₂
  • Molecular Weight 225.08
  • Synonym(s) Pyrimidine, 4,6-dichloro-2-phenyl-
  • SMILES C2=C(C1=NC(=CC(=N1)Cl)Cl)C=CC=C2

Description

4,6-Dichloro-2-phenylpyrimidine features a sterically hindered pyrimidine core with electron-withdrawing chloro groups at the 4 and 6 positions, paired with a phenyl substituent at the 2 position. This configuration enhances electrophilic reactivity and stability under standard conditions, enabling efficient coupling in cross-coupling and heterocycle formation reactions.

Application

4,6-Dichloro-2-phenylpyrimidine serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The dichloropyrimidine core exhibits high reactivity toward nucleophiles, facilitating the construction of complex heterocyclic scaffolds with predictable regioselectivity. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step syntheses requiring robust functional group tolerance and compatibility with diverse reaction conditions.

Synthesis

  • Route1

    References

    • Castelhano, Arlindo; McKibben, Bryan; Steinig, Arno; Collington, Eric Patent: US2003/162764 A1, 2003 ; US 20030162764 A1
  • Route2
    • In-stock
      4,6-Dichloropyrimidine|CS-W018513
      1193-21-1
    • null|null
      108-86-1
    • ~33%
    • In-stock
      4,6-Dichloro-2-phenylpyrimidine|CS-W013048
      3740-92-9

    References

    • MIIKANA THERAPEUTICS, INC. Patent: WO2008/154026 A1, 2008 ; Location in patent: Page/Page column 88 ; WO 2008/154026 A1
  • Route3
    • null|null
      591-51-5
    • ~%
    • In-stock
      4,6-Dichloro-2-phenylpyrimidine|CS-W013048
      3740-92-9

    References

    • Harden, Donald B.; Mokrosz, Maria J.; Strekowski, Lucjan Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 4137 - 4140

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

Quality Control

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Computational Chemistry Data

  • TPSA   25.78
  • LogP   3.4504
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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