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CS-W001157 4
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4-Amino-2-chloropyridine-3-carboxylic acid

  • CAS No. 1018678-38-0

  • Cat. No. CS-0051052
  • Purity≥98%
  • MDL No.None

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

4-Amino-2-chloropyridine-3-carboxylic acid|CS-0051052

Structure of 1018678-38-0

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General Information

  • CAS No. 1018678-38-0
  • Cat. No. CS-0051052
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅ClN₂O₂
  • Molecular Weight 172.57
  • Synonym(s) 4-Amino-2-chloronicotinic acid
  • SMILES NC1=C(C(O)=O)C(Cl)=NC=C1

Description

4-Amino-2-chloropyridine-3-carboxylic acid features a conjugated pyridine core bearing electron-donating amino and electron-withdrawing chloro and carboxylic acid groups, enabling versatile integration into pharmaceutical scaffolds. This arrangement supports hydrogen bonding and dipole interactions, enhancing solubility and binding affinity in target-directed synthesis.

Application

4-Amino-2-chloropyridine-3-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of pyridine-based heterocycles through palladium-catalyzed cross-coupling and electrophilic substitution reactions. Its orthogonal functional groups—amino, chloro, and carboxylic acid—support sequential transformations under mild conditions, facilitating efficient derivatization for API development. The compound exhibits good bench stability and is readily purified by recrystallization or chromatography, making it suitable for scalable synthetic workflows.

Synthesis

  • Route1
    • In-stock
      Methyl 4-amino-2-chloropyridine-3-carboxylate|CS-0049060
      1018678-37-9
    • ~66%
    • In-stock
      4-Amino-2-chloropyridine-3-carboxylic acid|CS-0051052
      1018678-38-0

    References

    • Pfizer Inc Patent: US2008/85887 A1, 2008 ; Location in patent: Page/Page column 18 ; US 20080085887 A1
  • Route2
    • tert-Butyl 4-((tert-butoxycarbonyl)amino)-2-chloronicotinate|CS-0909681
      1044148-93-7
    • ~%
    • In-stock
      4-Amino-2-chloropyridine-3-carboxylic acid|CS-0051052
      1018678-38-0

    References

    • Liu, Yahua; Ding, Qiang; Wu, Xu Synthesis, 2010 , # 1 p. 30 - 32

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   76.21
  • LogP   1.0154
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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