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CS-W001157 4
Total: USD 88.00

2-Amino-6-chloronicotinic acid

  • CAS No. 58584-92-2

  • Cat. No. CS-B0235
  • Purity≥97%
  • MDL No.MFCD11045328

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

2-Amino-6-chloronicotinic acid|CS-B0235

Structure of 58584-92-2

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General Information

  • CAS No. 58584-92-2
  • Cat. No. CS-B0235
  • Purity ≥97%
  • MDL No. MFCD11045328
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅ClN₂O₂
  • Molecular Weight 172.57
  • Synonym(s) 2-Amino-6-chloropyridine-3-carboxylicacid
  • SMILES O=C(O)C(C(N)=N1)=CC=C1Cl

Description

2-Amino-6-chloronicotinic acid features a chlorinated pyridine core with complementary amino and carboxylic acid functionalities, enabling direct integration into bioactive molecule scaffolds. This bench-stable derivative supports efficient coupling reactions and serves as a key building block in medicinal chemistry campaigns targeting heterocyclic pharmacophores.

Application

2-Amino-6-chloronicotinic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its ortho-amino and chloro substituents facilitate directed metalation, Suzuki-Miyaura coupling, and nucleophilic substitution reactions. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for iterative synthetic workflows in API development.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB Patent: US2009/99174 A1, 2009 ;
  • Route2

    References

    • Eisai RandD Management Co., Ltd. Patent: EP1864980 A1, 2007 ; Location in patent: Page/Page column 37-38 ;
  • Route3
    • null|null
      64-17-5
    • In-stock
      2-Amino-6-chloronicotinonitrile|CS-W021576
      52471-07-5
    • ~54%
    • null|null
      1384985-48-1
    • In-stock
      2-Amino-6-chloronicotinic acid|CS-B0235
      58584-92-2

    References

    • Kim, Hyo-Joong; Chen, Fei; Benner, Steven A. Journal of Organic Chemistry, 2012 , vol. 77, # 7 p. 3664 - 3669

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-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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