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2-Iodo-6-methoxypyridine

  • CAS No. 182275-70-3

  • Cat. No. CS-0037881
  • Purity≥97%
  • MDL No.MFCD07366733

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

2-Iodo-6-methoxypyridine|CS-0037881

Structure of 182275-70-3

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General Information

  • CAS No. 182275-70-3
  • Cat. No. CS-0037881
  • Purity ≥97%
  • MDL No. MFCD07366733
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆INO
  • Molecular Weight 235.02
  • Synonym(s) 2-Iodo-6-Methoxy-Pyridine
  • SMILES COC1=CC=CC(=N1)I

Description

2-Iodo-6-methoxypyridine is a bench-stable, moisture-tolerant heterocyclic building block featuring a reactive iodide at the 2-position and a methoxy group at the 6-position. This strategic substitution pattern enables efficient cross-coupling reactions in late-stage functionalization, particularly in palladium-catalyzed processes. The electron-deficient pyridine core enhances reactivity in nucleophilic displacement, facilitating rapid access to complex substituted pyridines under mild conditions.

Application

2-Iodo-6-methoxypyridine serves as a versatile building block in cross-coupling reactions, enabling efficient construction of biaryl and heterocyclic architectures. The iodide group facilitates reliable Suzuki, Stille, and Negishi couplings under standard conditions, while the methoxy substituent provides orthogonal reactivity and enhanced solubility. Its bench-stable nature and compatibility with diverse functional groups make it well-suited for medicinal chemistry and process-scale synthesis.

Synthesis

  • Route1

    References

    • Struk, Lukasz; Sosnicki, Jacek G. Synthesis, 2012 , vol. 44, # 5 p. 735 - 746
  • Route2
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    • In-stock
      2-Iodo-6-methoxypyridine|CS-0037881
      182275-70-3

    References

    • Chemistry - A European Journal, , vol. 4, # 1 p. 67 - 83
  • Route3
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      86609-15-6
    • ~%
    • In-stock
      2-Iodo-6-methoxypyridine|CS-0037881
      182275-70-3

    References

    • Jaric, Milica; Haag, Benjamin A.; Unsinn, Andreas; Karaghiosoff, Konstantin; Knochel, Paul Angewandte Chemie - International Edition, 2010 , vol. 49, # 32 p. 5451 - 5455

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   22.12
  • LogP   1.6948
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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