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CS-W001157 4
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4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

  • CAS No. 148256-82-0

  • Cat. No. CS-0050941
  • Purity≥98%
  • MDL No.None

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

4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde|CS-0050941

Structure of 148256-82-0

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General Information

  • CAS No. 148256-82-0
  • Cat. No. CS-0050941
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅ClN₂OS
  • Molecular Weight 188.63
  • Synonym(s) 4-Chloro-2-(methylthio)pyrimidine-5-carboxaldehyde
  • SMILES CSC1=NC=C(C=O)C(Cl)=N1

Description

4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde features a pyrimidine core bearing a chloro group, a methylthio substituent, and a formyl function at the 5-position. This electron-deficient scaffold integrates readily into heterocyclic syntheses, offering high reactivity in nucleophilic addition and coupling processes. The aldehyde functionality enables direct conjugation with amines or hydrazines under mild conditions. Bench-stable and moisture-tolerant, it serves as a key building block for pharmaceutical intermediates and functional materials.

Application

4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling efficient construction of pyrimidine-based scaffolds. The aldehyde group facilitates nucleophilic additions and condensation reactions, while the chloro and methylthio substituents offer orthogonal reactivity for downstream functionalization. Bench-stable and compatible with standard purification methods, it functions effectively in coupling and heterocycle-forming processes common to API development.

Synthesis

  • Route1

    References

    • AMGEN INC. Patent: WO2009/85185 A1, 2009 ; Location in patent: Page/Page column 129 ; WO 2009/085185 A1
  • Route2
    • Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate Avanafil  Impurity|CS-0228709
      5909-24-0
    • ~%
    • In-stock
      4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde|CS-0050941
      148256-82-0

    References

    • HUTCHISON MEDIPHARMA LIMITED; SU, Wei-guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; ZHANG, Zhulin; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; CHAI, Wenying Patent: WO2014/15830 A1, 2014 ;
  • Route3
    • null|null
      49844-90-8
    • ~%
    • In-stock
      4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde|CS-0050941
      148256-82-0

    References

    • Ple; Turck; Martin; Barbey; Queguiner Tetrahedron Letters, 1993 , vol. 34, # 10 p. 1605 - 1608

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   42.85
  • LogP   1.6644
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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