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CS-W001157 4
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3-Chloro-2-methoxypyridine

  • CAS No. 13472-84-9

  • Cat. No. CS-W003028
  • Purity≥98%
  • MDL No.MFCD03095227

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

3-Chloro-2-methoxypyridine|CS-W003028

Structure of 13472-84-9

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General Information

  • CAS No. 13472-84-9
  • Cat. No. CS-W003028
  • Purity ≥98%
  • MDL No. MFCD03095227
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆ClNO
  • Molecular Weight 143.57
  • Synonym(s) 2-Methoxy-3-Chloropyridine
  • SMILES COC1=C(Cl)C=CC=N1

Description

3-Chloro-2-methoxypyridine features a pyridine ring functionalized with chlorine at the 3-position and methoxy at the 2-position, delivering enhanced reactivity in cross-coupling and nucleophilic substitution processes. The electron-withdrawing chlorine and electron-donating methoxy groups create a balanced electronic profile, enabling selective transformations under mild conditions. This bench-stable heterocycle serves as a key building block for pharmaceutical intermediates and agrochemical scaffolds.

Application

3-Chloro-2-methoxypyridine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its reactive C–Cl bond and ortho-methoxy directing group. The methoxy substituent enhances solubility and stabilizes the pyridine ring toward nucleophilic attack, while the chlorine facilitates functionalization under mild conditions. Its bench-stable nature and compatibility with diverse reaction partners make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1

    References

    • Testaferri, Lorenzo; Tiecco, Marcello; Tingoli, Marco; Bartoli, Donatella; Massoli, Alberto Tetrahedron, 1985 , vol. 41, # 7 p. 1373 - 1384
  • Route2
    • In-stock
      2,3-Dichloropyridine|CS-W013307
      2402-77-9
    • null|null
      124-41-4
    • ~71%
    • In-stock
      3-Chloro-2-methoxypyridine|CS-W003028
      13472-84-9

    References

    • Tiecco, Marcello Bulletin des Societes Chimiques Belges, 1986 , vol. 95, # 11 p. 1009 - 1020
  • Route3
    • In-stock
      2,3-Dichloropyridine|CS-W013307
      2402-77-9
    • null|null
      67-56-1
    • ~80%
    • In-stock
      3-Chloro-2-methoxypyridine|CS-W003028
      13472-84-9

    References

    • Connon, Stephen J.; Hegarty, Anthony F. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 8 p. 1245 - 1249

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

Quality Control

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Computational Chemistry Data

  • TPSA   22.12
  • LogP   1.7436
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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