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CS-W001157 4
Total: USD 88.00

3-Methylpyridine-2-carboxaldehyde

  • CAS No. 55589-47-4

  • Cat. No. CS-W002921
  • Purity≥96%
  • MDL No.MFCD02181144

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

3-Methylpyridine-2-carboxaldehyde|CS-W002921

Structure of 55589-47-4

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General Information

  • CAS No. 55589-47-4
  • Cat. No. CS-W002921
  • Purity ≥96%
  • MDL No. MFCD02181144
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇NO
  • Molecular Weight None
  • Synonym(s) 3-Methylpyridine-2-carbaldehyde
  • SMILES CC(C=CC=N1)=C1C=O

Description

3-Methylpyridine-2-carboxaldehyde features a pyridine ring bearing a methyl group at the 3-position and an aldehyde functionality at the 2-position, creating a rigid, electron-deficient heteroaromatic scaffold. This configuration enables direct integration into transition metal-catalyzed coupling reactions and facilitates coordination in ligand design for catalytic systems requiring strong π-acidity. The aldehyde group remains stable under standard handling conditions, allowing straightforward derivatization via imine formation or reductive amination.

Application

3-Methylpyridine-2-carboxaldehyde serves as a versatile building block in synthetic organic chemistry, enabling the construction of bioactive heterocycles and pharmaceutical intermediates. Its ortho-aldehyde functionality facilitates efficient imine formation, Mannich reactions, and transition-metal-catalyzed couplings. The methyl group enhances regioselectivity in electrophilic substitutions, while the aldehyde remains stable under standard bench conditions, allowing straightforward handling and purification.

Synthesis

  • Route1

    References

    • Iqbal, Nadeem; Akula, Murthy R.; Vo, Dean; Matowe, Wandikayi C.; McEwen, Carol-Anne; Wolowyk, Michael W.; Knaus, Edward E. Journal of Medicinal Chemistry, 1998 , vol. 41, # 11 p. 1827 - 1837
  • Route2

    References

    • Meiji Seika Kaisha, Ltd. Patent: EP1180514 A1, 2002 ; Location in patent: Example 103 ;
  • Route3
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    • In-stock
      3-Methylpyridine-2-carboxaldehyde|CS-W002921
      55589-47-4

    References

    • Journal of the American Chemical Society, , vol. 79, p. 481,483

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H302-H315-H319-H335
Precautionary Statements : P210-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P370+P378-P403-P405-P501

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Computational Chemistry Data

  • TPSA   29.96
  • LogP   1.20252
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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