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CS-W001157 4
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5-Iodopyridin-2-amine

  • CAS No. 20511-12-0

  • Cat. No. CS-W013150
  • Purity≥98%
  • MDL No.MFCD00160312

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

5-Iodopyridin-2-amine|CS-W013150

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General Information

  • CAS No. 20511-12-0
  • Cat. No. CS-W013150
  • Purity ≥98%
  • MDL No. MFCD00160312
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅IN₂
  • Molecular Weight 220.01
  • Synonym(s) 5-Iodo-2-pyridinamine
  • SMILES IC1=CC=C(N)N=C1

Description

5-Iodopyridin-2-amine serves as a pivotal building block in cross-coupling chemistry, featuring a reactive iodide at the 5-position and a nucleophilic amine at the 2-position. This dual functionality enables seamless integration into diverse synthetic scaffolds, particularly in the development of pharmaceuticals and functional materials. The molecule exhibits excellent stability under standard conditions and facilitates efficient Pd-catalyzed transformations.

Application

5-Iodopyridin-2-amine serves as a versatile building block in cross-coupling chemistry, enabling efficient Pd-catalyzed transformations such as Suzuki-Miyaura and Buchwald-Hartwig reactions. The iodide group provides high reactivity under standard conditions, while the pyridin-2-amine moiety offers orthogonal functionality for further derivatization. This compound exhibits excellent bench stability and is compatible with a wide range of functional groups, facilitating rapid access to biologically relevant heterocyclic scaffolds.

Synthesis

  • Route1
    • null|null
      504-29-0
    • ~83%
    • In-stock
      5-Iodopyridin-2-amine|CS-W013150
      20511-12-0

    References

    • Martinez-Urbina, Miguel Angel; Zentella, Alejandro; Vilchis-Reyes, Miguel Angel; Guzman, Angel; Vargas, Omar; Ramirez Apan, Maria Teresa; Ventura Gallegos, Jose Luis; Diaz, Eduardo European Journal of Medicinal Chemistry, 2010 , vol. 45, # 3 p. 1211 - 1219
  • Route2

    References

    • Klapars, Artis; Buchwald, Stephen L. Journal of the American Chemical Society, 2002 , vol. 124, # 50 p. 14844 - 14845
  • Route3
    • null|null
      157020-27-4
    • ~79%
    • In-stock
      5-Iodopyridin-2-amine|CS-W013150
      20511-12-0

    References

    • Burgos; Delgado; Garcia-Navio; Izquierdo; Alvarez-Builla Tetrahedron, 1995 , vol. 51, # 31 p. 8649 - 8654

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

Quality Control

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Computational Chemistry Data

  • TPSA   38.91
  • LogP   1.2684
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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