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CS-W001157 4
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6-Bromo-2-methoxynicotinaldehyde

  • CAS No. 58819-88-8

  • Cat. No. CS-0042096
  • Molecule weight216.03
  • Purity≥98%
  • MDL No.None

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

6-Bromo-2-methoxynicotinaldehyde|CS-0042096

Structure of 58819-88-8

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General Information

  • CAS No. 58819-88-8
  • Cat. No. CS-0042096
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₂
  • Molecular Weight 216.03
  • Synonym(s) 2-Methoxy-3-formyl-6-brompyridin
  • SMILES O=CC1=C(OC)N=C(Br)C=C1

Description

6-Bromo-2-methoxynicotinaldehyde features a bromine substituent at the 6-position and a methoxy group at the 2-position on a nicotinaldehyde scaffold. This electron-deficient aldehyde integrates readily into cross-coupling reactions, offering enhanced reactivity in synthetic sequences requiring halogen-functionalized heteroaromatics.

Application

6-Bromo-2-methoxynicotinaldehyde serves as a versatile building block in medicinal chemistry, enabling direct incorporation of bromo and methoxy-functionalized pyridine scaffolds into target molecules. Its aldehyde functionality facilitates efficient coupling reactions, including reductive amination and Wittig transformations, while the bromine atom supports palladium-catalyzed cross-coupling protocols such as Suzuki-Miyaura and Stille reactions. The compound exhibits good bench stability and is readily purified by flash chromatography, making it well-suited for iterative synthesis campaigns and API precursor development.

Synthesis

  • Route1
    • 6-Bromo-3-iodo-2-methoxypyridine|CS-0463062
      1310949-37-1
    • null|null
      68-12-2
    • ~89%
    • In-stock
      6-Bromo-2-methoxynicotinaldehyde|CS-0042096
      58819-88-8

    References

    • TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD. Patent: US2011/237791 A1, 2011 ; Location in patent: Page/Page column 90 percent ;
  • Route2

    References

    • TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD. Patent: US2011/237791 A1, 2011 ;
  • Route3

    References

    • TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD. Patent: US2011/237791 A1, 2011 ;

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   1.6652
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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