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CS-W001157 4
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5-Chloro-2-formylpyridine

  • CAS No. 31181-89-2

  • Cat. No. CS-W003503
  • Purity≥97%
  • MDL No.MFCD08277271

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

5-Chloro-2-formylpyridine|CS-W003503

Structure of 31181-89-2

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General Information

  • CAS No. 31181-89-2
  • Cat. No. CS-W003503
  • Purity ≥97%
  • MDL No. MFCD08277271
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄ClNO
  • Molecular Weight 141.56
  • Synonym(s) 5-Chloropicolinaldehyde
  • SMILES O=Cc1ccc(cn1)Cl

Description

5-Chloro-2-formylpyridine features a strategically positioned formyl group flanked by a chlorine substituent, enabling direct incorporation into heterocyclic scaffolds. This electron-deficient pyridine derivative delivers high reactivity in nucleophilic addition and condensation reactions, particularly valuable in medicinal chemistry and catalyst design.

Application

5-Chloro-2-formylpyridine serves as a versatile building block in medicinal chemistry, enabling efficient access to functionalized heterocycles via electrophilic substitution, nucleophilic addition, and transition-metal-catalyzed coupling reactions. The ortho-formyl group facilitates directed metalation and cyclization, while the chloropyridine moiety supports palladium-mediated cross-coupling. Bench-stable and readily purified by distillation, it functions effectively in multi-step syntheses of kinase inhibitors and other bioactive scaffolds.

Synthesis

  • Route1
    • Ethyl 5-chloropicolinate|CS-0043157
      128072-93-5
    • ~53%
    • In-stock
      5-Chloro-2-formylpyridine|CS-W003503
      31181-89-2

    References

    • ASTRAZENECA AB; NPS PHARMACEUTICALS, INC. Patent: WO2004/14902 A2, 2004 ; Location in patent: Page 42 ; WO 2004/014902 A2
  • Route2
    • null|null
      68-12-2
    • In-stock
      5-Chloro-2-iodopyridine|CS-W019023
      244221-57-6
    • ~%
    • In-stock
      5-Chloro-2-formylpyridine|CS-W003503
      31181-89-2

    References

    • WO2007/15162 A1, ; Page/Page column 91 ; WO 2007/015162 A1
  • Route3
    • null|null
      68-12-2
    • ~%
    • In-stock
      5-Chloro-2-formylpyridine|CS-W003503
      31181-89-2

    References

    • WO2007/96763 A2, ; Page/Page column 52 ; WO 2007/096763 A2

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   29.96
  • LogP   1.5475
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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