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CS-W001157 4
Total: USD 88.00

4-Methoxypicolinaldehyde

  • CAS No. 16744-81-3

  • Cat. No. CS-W004971
  • Purity≥98%
  • MDL No.MFCD08234865

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

4-Methoxypicolinaldehyde|CS-W004971

Structure of 16744-81-3

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General Information

  • CAS No. 16744-81-3
  • Cat. No. CS-W004971
  • Purity ≥98%
  • MDL No. MFCD08234865
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇NO₂
  • Molecular Weight 137.14
  • Synonym(s) 4-Methoxypyridine-2-carboxaldehyde
  • SMILES O=CC1=NC=CC(OC)=C1

Description

4-Methoxypicolinaldehyde features a pyridine ring with strategically positioned aldehyde and methoxy groups, enabling selective reactivity in cross-coupling and condensation reactions. This bench-stable, moisture-tolerant reagent integrates readily into synthetic pathways requiring electron-deficient heteroaryl platforms.

Application

4-Methoxypicolinaldehyde serves as a versatile building block in medicinal chemistry, enabling efficient construction of pyridine-based heterocycles. Its aldehyde functionality facilitates reductive amination, Ugi-type condensations, and coupling reactions with nucleophiles under mild conditions. The methoxy group enhances solubility and modulates electronic properties, while the compound exhibits good bench stability and ease of purification—making it suitable for high-throughput synthesis and scale-up applications.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2009/56886 A1, 2009 ; Location in patent: Page/Page column 54 ; WO 2009/056886 A1
  • Route2

    References

    • Donohoe, Timothy J.; Connolly, Matthew J.; Rathi, Akshat H.; Walton, Lesley Organic Letters, 2011 , vol. 13, # 8 p. 2074 - 2077
  • Route3
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      931-19-1
    • ~%
    • In-stock
      4-Methoxypicolinaldehyde|CS-W004971
      16744-81-3

    References

    • Chemical and Pharmaceutical Bulletin, , vol. 38, # 9 p. 2446 - 2458

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   39.19
  • LogP   0.9027
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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