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CS-W001157 4
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6-(Dimethylamino)nicotinaldehyde

  • CAS No. 149805-92-5

  • Cat. No. CS-0054399
  • Purity≥98%
  • MDL No.None

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

6-(Dimethylamino)nicotinaldehyde|CS-0054399

Structure of 149805-92-5

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General Information

  • CAS No. 149805-92-5
  • Cat. No. CS-0054399
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀N₂O
  • Molecular Weight 150.18
  • Synonym(s) 2-dimethylamino-5-formylpyridine
  • SMILES O=CC1=CN=C(N(C)C)C=C1

Description

6-(Dimethylamino)nicotinaldehyde features a pyridine ring bearing an electron-rich dimethylamino group and a reactive aldehyde at the 6-position. This combination enables selective conjugation in bioconjugation workflows and facilitates incorporation into fluorescent probes. The compound exhibits enhanced solubility and stability under standard bench conditions, supporting efficient synthesis and handling in medicinal chemistry applications.

Application

6-(Dimethylamino)nicotinaldehyde serves as a versatile building block in medicinal chemistry, enabling the synthesis of pyridine-based scaffolds through condensation and coupling reactions. Its aldehyde functionality facilitates efficient derivatization, while the dimethylamino group enhances electron density at the pyridine ring, promoting reactivity in nucleophilic additions and transition-metal-catalyzed transformations. The compound exhibits bench stability and is compatible with standard purification protocols, making it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1
    • In-stock
      2-Pyridinamine, 5-bromo-N,N-dimethyl-|CS-0030447
      26163-07-5
    • null|null
      20485-44-3
    • ~90%
    • In-stock
      6-(Dimethylamino)nicotinaldehyde|CS-0054399
      149805-92-5

    References

    • Eisai Co., Ltd. Patent: US2002/19531 A1, 2002 ; US 20020019531 A1
  • Route2
    • In-stock
      2-Pyridinamine, 5-bromo-N,N-dimethyl-|CS-0030447
      26163-07-5
    • null|null
      68-12-2
    • ~%
    • In-stock
      6-(Dimethylamino)nicotinaldehyde|CS-0054399
      149805-92-5

    References

    • Journal of Medicinal Chemistry, , vol. 47, # 19 p. 4787 - 4798
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 47, # 19 p. 4787 - 4798

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   33.2
  • LogP   0.9601
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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