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CS-W001157 4
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5-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione

  • CAS No. 16018-87-4

  • Cat. No. CS-0059294
  • Purity≥98%
  • MDL No.None

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

5-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione|CS-0059294

Structure of 16018-87-4

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General Information

  • CAS No. 16018-87-4
  • Cat. No. CS-0059294
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅ClN₂O₂
  • Molecular Weight 160.56
  • Synonym(s) 5-Chloro-6-methyluracil
  • SMILES O=C1NC(C(Cl)=C(C)N1)=O

Description

5-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione features a chlorinated pyrimidinedione core with a methyl group at the 6-position, conferring enhanced electrophilicity and stability. This scaffold serves as a key building block in medicinal chemistry, particularly for heterocyclic scaffolds requiring precise electronic tuning and metabolic resistance.

Application

5-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyrimidine scaffolds. Its electrophilic chlorine and acidic enolizable protons facilitate nucleophilic substitution and condensation reactions under mild conditions. The compound exhibits good bench stability and compatibility with common functional groups, making it suitable for iterative synthesis workflows in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Kasradze; Ignatyeva; Khusnutdinov; Suponitskii, K. Yu.; Antipin, M. Yu.; Yunusov Chemistry of Heterocyclic Compounds, 2012 , vol. 48, # 7 p. 1018 - 1027 Khim. Geterotsikl. Soedin., 2012 , vol. 48, # 7 p. 1095 - 1106,12
  • Route2
    • In-stock
      6-Methyluracil|CS-0017143
      626-48-2
    • ~81%
    • In-stock
      5-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione|CS-0059294
      16018-87-4
    • null|null
      50610-49-6

    References

    • Chemistry of Heterocyclic Compounds, , vol. 48, # 7 p. 1018 - 1027 Khim. Geterotsikl. Soedin., , vol. 48, # 7 p. 1095 - 1106,12
  • Route3
    • null|null
      873422-37-8
    • ~%
    • In-stock
      5-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione|CS-0059294
      16018-87-4

    References

    • Journal of the American Chemical Society, , vol. 60, p. 1622

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   65.72
  • LogP   0.02502
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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