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CS-W001157 4
Total: USD 88.00

2-Iodo-3-pyridinol

  • CAS No. 40263-57-8

  • Cat. No. CS-D1763
  • Purity≥97%
  • MDL No.MFCD00023421

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

2-Iodo-3-pyridinol|CS-D1763

Structure of 40263-57-8

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General Information

  • CAS No. 40263-57-8
  • Cat. No. CS-D1763
  • Purity ≥97%
  • MDL No. MFCD00023421
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄INO
  • Molecular Weight 221.00
  • Synonym(s) 2-Iodo-3-hydroxypyridine; 3-Hydroxy-2-iodopyridine; NSC 103161; Pyridine, 2-iodo-3-hydroxy-
  • SMILES OC1=CC=CN=C1I

Description

2-Iodo-3-pyridinol delivers a reactive iodine handle at the 2-position of a pyridinol scaffold, enabling efficient cross-coupling transformations. The ortho-hydroxyl group enhances solubility and participates in coordination or hydrogen bonding, while the electron-deficient pyridine ring supports stable reaction intermediates under standard conditions. This structure facilitates integration into bioactive scaffolds and functional materials.

Application

2-Iodo-3-pyridinol serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable iodide functionality and ortho-hydroxyl group. The pyridinol scaffold provides enhanced solubility and hydrogen-bonding capacity, facilitating downstream derivatization in heterocyclic synthesis. Its bench-stable nature and compatibility with common reaction conditions make it well-suited for iterative coupling strategies in API development.

Synthesis

  • Route1

    References

    • Loidreau, Yvonnick; Marchand, Pascal; Dubouilh-Benard, Carole; Nourrisson, Marie-Renee; Duflos, Muriel; Besson, Thierry Tetrahedron Letters, 2012 , vol. 53, # 8 p. 944 - 947
  • Route2
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      3-Hydroxypyridine|CS-W009147
      109-00-2
    • ~80%
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      2-Iodo-3-pyridinol|CS-D1763
      40263-57-8
    • 2,6-Diiodopyridin-3-ol|CS-0320913
      14764-90-0
    • null|null
      67868-14-8

    References

    • Koch; Schnatterer Synthesis, 1990 , # 6 p. 497 - 498
  • Route3

    References

    • Eisai Co., Ltd. Patent: US6340759 B1, 2002 ; Location in patent: Example 127 ;

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   33.12
  • LogP   1.3918
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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