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1-(5-Bromo-2-chloropyridin-3-yl)ethanone

  • CAS No. 886365-47-5

  • Cat. No. CS-0021075
  • Molecule weight234.48
  • Purity≥98%
  • MDL No.MFCD08436181

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

1-(5-Bromo-2-chloropyridin-3-yl)ethanone|CS-0021075

Structure of 886365-47-5

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General Information

  • CAS No. 886365-47-5
  • Cat. No. CS-0021075
  • Purity ≥98%
  • MDL No. MFCD08436181
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrClNO
  • Molecular Weight 234.48
  • Synonym(s) 1-(5-Bromo-2-chloropyridin-3-yl)ethanone
  • SMILES CC(C1=CC(Br)=CN=C1Cl)=O

Description

1-(5-Bromo-2-chloropyridin-3-yl)ethanone features a bromo-chloro-substituted pyridine core paired with an acetyl group, enabling direct integration into Suzuki and Buchwald-Hartwig coupling cascades. The electron-deficient heterocycle enhances reactivity in cross-coupling protocols, while the bench-stable ketone functionality simplifies handling under standard conditions.

Application

1-(5-Bromo-2-chloropyridin-3-yl)ethanone serves as a versatile building block in medicinal chemistry, enabling efficient construction of pyridine-based scaffolds. Its bromo and chloro substituents provide orthogonal handles for palladium-catalyzed cross-coupling reactions, while the acetyl group offers a readily modifiable site for further functionalization. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis campaigns in API development.

Synthesis

  • Route1
    • 5-Bromo-2-chloro-N-methoxy-N-methylnicotinamide|CS-0082379
      885223-63-2
    • ~92%
    • In-stock
      1-(5-Bromo-2-chloropyridin-3-yl)ethanone|CS-0021075
      886365-47-5

    References

    • Lin, Songwen; Han, Fangbin; Liu, Peng; Tao, Jing; Zhong, Xuechao; Liu, Xiujie; Yi, Chongqin; Xu, Heng Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 3 p. 790 - 793
  • Route2
    • 1-(5-Bromo-2-chloropyridin-3-yl)ethanol|CS-0369254
      1111638-41-5
    • ~76%
    • In-stock
      1-(5-Bromo-2-chloropyridin-3-yl)ethanone|CS-0021075
      886365-47-5

    References

    • PFIZER INC. Patent: WO2009/16460 A2, 2009 ; Location in patent: Page/Page column 104-105 ; WO 2009/016460 A2
  • Route3
    • 5-Bromo-2-chloro-N-methoxy-N-methylnicotinamide|CS-0082379
      885223-63-2
    • null|null
      75-16-1
    • ~54%
    • In-stock
      1-(5-Bromo-2-chloropyridin-3-yl)ethanone|CS-0021075
      886365-47-5

    References

    • AMGEN, INC. Patent: WO2006/44860 A2, 2006 ; Location in patent: Page/Page column 43-44 ; WO 2006/044860 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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   29.96
  • LogP   2.7001
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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