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CS-W001157 4
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4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid

  • CAS No. 74840-34-9

  • Cat. No. CS-0045703
  • Purity≥95%
  • MDL No.MFCD06643376

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

4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid|CS-0045703

Structure of 74840-34-9

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General Information

  • CAS No. 74840-34-9
  • Cat. No. CS-0045703
  • Purity ≥95%
  • MDL No. MFCD06643376
  • Storage -20°C, stored under nitrogen, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅ClN₂O₂S
  • Molecular Weight 204.63
  • Synonym(s) 4-Chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid
  • SMILES O=C(C1=CN=C(SC)N=C1Cl)O

Description

4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid is a heterocyclic building block featuring a chlorine atom at C4, a methylthio group at C2, and a carboxylic acid at C5. This combination delivers enhanced electrophilicity and solubility in polar solvents, enabling efficient coupling reactions in medicinal chemistry applications. The molecule exhibits bench-stable handling under standard conditions.

Application

4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrimidine-based scaffolds through nucleophilic substitution and coupling reactions. The chloro group facilitates C–N and C–C bond formation under standard conditions, while the carboxylic acid enables amide coupling or esterification for downstream derivatization. The methylthio substituent provides orthogonal reactivity and enhances metabolic stability in target molecules. Bench-stable and readily purified by recrystallization, it supports scalable synthesis of bioactive intermediates.

Synthesis

  • Route1
    • Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate Avanafil  Impurity|CS-0228709
      5909-24-0
    • ~%
    • In-stock
      4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid|CS-0045703
      74840-34-9

    References

    • US2008/114007 A1, ; Page/Page column 82 ;

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   63.08
  • LogP   1.5501
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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