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CS-W001157 4
Total: USD 88.00

3-Amino-6-chloroisonicotinic acid

  • CAS No. 58483-95-7

  • Cat. No. CS-W009220
  • Purity≥98%
  • MDL No.MFCD06659499

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

3-Amino-6-chloroisonicotinic acid|CS-W009220

Structure of 58483-95-7

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General Information

  • CAS No. 58483-95-7
  • Cat. No. CS-W009220
  • Purity ≥98%
  • MDL No. MFCD06659499
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅ClN₂O₂
  • Molecular Weight 172.57
  • Synonym(s) 5-Amino-2-chloropyridine-4-carboxylic acid
  • SMILES O=C(O)C1=CC(Cl)=NC=C1N

Description

3-Amino-6-chloroisonicotinic acid is a bench-stable, electron-deficient heterocyclic scaffold featuring a para-chloro and ortho-amino substitution on the pyridine ring. This configuration enables direct integration into pharmaceutical intermediates and bioactive molecule synthesis, where its dual functional groups facilitate selective coupling reactions under standard conditions.

Application

3-Amino-6-chloroisonicotinic acid serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles through standard coupling and cyclization protocols. Its ortho-amino and chloro substituents offer complementary reactivity for palladium-catalyzed cross-couplings and electrophilic substitutions, while the carboxylic acid facilitates amide formation and derivatization. The compound exhibits good bench stability and is readily purified by recrystallization, supporting its use in scalable synthesis of pharmaceutical intermediates and functionalized pyridine scaffolds.

Synthesis

  • Route1

    References

    • Warner-Lambert Company Patent: US5654307 A1, 1997 ; US 5654307 A
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 11, # 11 p. 1401 - 1405
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 11, # 11 p. 1401 - 1405

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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