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CS-W001157 4
Total: USD 88.00

4-Amino-3-iodopyridine

  • CAS No. 88511-27-7

  • Cat. No. CS-W002945
  • Purity≥97%
  • MDL No.MFCD02663853

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

4-Amino-3-iodopyridine|CS-W002945

Structure of 88511-27-7

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General Information

  • CAS No. 88511-27-7
  • Cat. No. CS-W002945
  • Purity ≥97%
  • MDL No. MFCD02663853
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅IN₂
  • Molecular Weight 220.01
  • Synonym(s) 3-Iodo-4-pyridinamine
  • SMILES Nc1ccncc1I

Description

4-Amino-3-iodopyridine serves as a key building block in the synthesis of functionalized heterocycles, featuring a strategically positioned amino group and iodine atom for orthogonal derivatization. This electron-rich pyridine scaffold enables efficient cross-coupling reactions and facilitates incorporation into bioactive molecules. The compound exhibits bench-stable handling characteristics and compatibility with diverse reaction conditions.

Application

4-Amino-3-iodopyridine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl and heteroaryl scaffolds. The ortho-iodo group facilitates efficient Suzuki-Miyaura and Stille couplings, while the primary amino functionality allows for direct derivatization or protection. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for synthesizing complex nitrogen-containing architectures.

Synthesis

  • Route1
    • null|null
      504-24-5
    • ~88%
    • In-stock
      4-Amino-3-iodopyridine|CS-W002945
      88511-27-7

    References

    • Yusubov, Mekhman S.; Yusubova, Roza Y.; Nemykin, Victor N.; Maskaev, Andrey V.; Geraskina, Margarita R.; Kirschning, Andreas; Zhdankin, Viktor V. European Journal of Organic Chemistry, 2012 , # 30 p. 5935 - 5942,8
  • Route2

    References

    • Lee, Hyang-Yeol; Yerkes, Nancy; O'Connor, Sarah E. Chemistry and Biology, 2009 , vol. 16, # 12 p. 1225 - 1229
  • Route3
    • null|null
      504-24-5
    • ~33%
    • In-stock
      4-Amino-3-iodopyridine|CS-W002945
      88511-27-7
    • In-stock
      3,5-Diiodopyridin-4-amine|CS-W011886
      98136-86-8

    References

    • Journal of Organic Chemistry, , vol. 77, # 11 p. 5006 - 5016

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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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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