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6-Chloronicotinamide

  • CAS No. 6271-78-9

  • Cat. No. CS-0128795
  • Purity≥97%
  • MDL No.MFCD00006242

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

6-Chloronicotinamide|CS-0128795

Structure of 6271-78-9

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General Information

  • CAS No. 6271-78-9
  • Cat. No. CS-0128795
  • Purity ≥97%
  • MDL No. MFCD00006242
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅ClN₂O
  • Molecular Weight 156.57
  • Synonym(s) 6-Chloropyridine-3-carboxamide; 6-Chloronicotinamide
  • SMILES O=C(C1=CC=C(Cl)N=C1)N

Description

6-Chloronicotinamide features a chlorinated pyridine core with a stable amide functional group, enabling direct incorporation into bioactive scaffolds. This bench-stable compound serves as a key building block in medicinal chemistry, particularly for targeting kinase pathways and optimizing pharmacokinetic profiles through halogen bonding interactions.

Application

6-Chloronicotinamide serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles through palladium-catalyzed cross-coupling reactions. Its chlorine substituent provides high reactivity in Suzuki, Stille, and Buchwald–Hartwig transformations, while the amide functionality offers enhanced solubility and metabolic stability. The compound exhibits excellent bench stability and is readily purified by recrystallization, facilitating integration into multi-step synthetic sequences for API development.

Synthesis

  • Route1

    References

    • Wang, Qing Min; Sun, Hui Kai; Huang, Run Qiu Heteroatom Chemistry, 2004 , vol. 15, # 1 p. 67 - 70
  • Route2

    References

    • Bioorganic and Medicinal Chemistry, , vol. 12, # 4 p. 655 - 662
  • Route3
    • 6-Hydroxynicotinic acid Avatrombopag Impurity|CS-0377520
      5006-66-6
    • ~%
    • In-stock
      6-Chloronicotinamide|CS-0128795
      6271-78-9

    References

    • Journal of the Chemical Society, , vol. 93, p. 1379

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   55.98
  • LogP   0.8339
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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