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CS-W001157 4
Total: USD 88.00

4-Amino-2-chloroquinazoline

  • CAS No. 59870-43-8

  • Cat. No. CS-0031660
  • Purity≥97%
  • MDL No.MFCD08234547

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

4-Amino-2-chloroquinazoline|CS-0031660

Structure of 59870-43-8

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General Information

  • CAS No. 59870-43-8
  • Cat. No. CS-0031660
  • Purity ≥97%
  • MDL No. MFCD08234547
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆ClN₃
  • Molecular Weight 179.61
  • Synonym(s) NSC 75185; 2-Chloroquinazolin-4-amine
  • SMILES NC1=C2C=CC=CC2=NC(Cl)=N1

Description

4-Amino-2-chloroquinazoline is a bench-stable heterocyclic scaffold featuring a chlorine atom at the 2-position and an amino group at the 4-position, enabling selective coupling reactions. This electron-deficient core integrates readily into kinase inhibitor architectures and serves as a key intermediate in medicinal chemistry campaigns targeting purine-binding sites.

Application

4-Amino-2-chloroquinazoline serves as a versatile building block in medicinal chemistry, enabling efficient access to quinazoline-based scaffolds through palladium-catalyzed cross-coupling and nucleophilic substitution reactions. Its well-defined reactivity profile—particularly the ortho-chloro group’s readiness for displacement—facilitates the synthesis of substituted analogs with enhanced pharmacological properties. Bench-stable and readily purified by recrystallization, it functions reliably in high-throughput screening campaigns and lead optimization workflows.

Synthesis

  • Route1

    References

    • Rueeger, Heinrich; Rigollier, Pascal; Yamaguchi, Yasuchika; Schmidlin, Tibur; Schilling, Walter; Criscione, Leoluca; Whitebread, Steven; Chiesi, Michele; Walker, Mary W.; Dhanoa, Dale; Islam, Imadul; Zhang, Jack; Gluchowski, Charles Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 11 p. 1175 - 1179
  • Route2
    • 2-Chloro-4-methoxyquinazoline|CS-0216008
      77767-98-7
    • ~%
    • In-stock
      4-Amino-2-chloroquinazoline|CS-0031660
      59870-43-8

    References

    • Journal of the American Chemical Society, , vol. 70, p. 4264
  • Route3
    • null|null
      1336-21-6
    • In-stock
      2,4-Dichloroquinazoline|CS-D0819
      607-68-1
    • ~%
    • In-stock
      4-Amino-2-chloroquinazoline|CS-0031660
      59870-43-8

    References

    • US3956495 A1, ; US 3956495 A

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   51.8
  • LogP   1.8654
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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