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CS-W001157 4
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5-Bromo-6-methoxynicotinaldehyde

  • CAS No. 65873-73-6

  • Cat. No. CS-0044359
  • Purity≥96%
  • MDL No.MFCD16606522

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

5-Bromo-6-methoxynicotinaldehyde|CS-0044359

Structure of 65873-73-6

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General Information

  • CAS No. 65873-73-6
  • Cat. No. CS-0044359
  • Purity ≥96%
  • MDL No. MFCD16606522
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₂
  • Molecular Weight 216.03
  • Synonym(s) 5-bromo-6-methoxypyridine-3-carbaldehyde
  • SMILES O=CC1=CC(Br)=C(OC)N=C1

Description

5-Bromo-6-methoxynicotinaldehyde delivers a reactive aldehyde handle flanked by electron-withdrawing bromo and methoxy substituents, enabling efficient coupling in cross-coupling and condensation reactions. This bench-stable, moisture-tolerant building block integrates seamlessly into complex heterocyclic architectures.

Application

5-Bromo-6-methoxynicotinaldehyde serves as a versatile building block in medicinal chemistry, enabling direct incorporation of bromo and methoxy functionalities into heterocyclic scaffolds. Its aldehyde group facilitates nucleophilic addition, reductive amination, and coupling reactions with amines or hydrazines, while the bromine atom supports palladium-catalyzed cross-coupling transformations. The methoxy substituent enhances solubility and modulates electronic properties, contributing to improved stability and handling during synthesis. This compound functions effectively in the construction of advanced intermediates for pharmaceutical development and functional materials.

Synthesis

  • Route1

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2009/155389 A1, 2009 ; Location in patent: Page/Page column 39-40 ; WO 2009/155389 A1
  • Route2
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      64-17-5
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      1219936-54-5
    • ~%
    • In-stock
      5-Bromo-6-methoxynicotinaldehyde|CS-0044359
      65873-73-6
    • null|null
      1214346-73-2

    References

    • AMIRA PHARMACEUTICALS, INC. Patent: US2010/81673 A1, 2010 ; Location in patent: Page/Page column 18 ; US 20100081673 A1
  • Route3

    References

    • Bargar, T. M.; Wilson, T.; Daniel, J. K. Journal of Heterocyclic Chemistry, 1985 , vol. 22, p. 1583 - 1592

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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