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CS-W001157 4
Total: USD 88.00

2,6-Dibromonicotinaldehyde

  • CAS No. 55304-83-1

  • Cat. No. CS-0052135
  • Purity≥97%
  • MDL No.None

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

2,6-Dibromonicotinaldehyde|CS-0052135

Structure of 55304-83-1

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General Information

  • CAS No. 55304-83-1
  • Cat. No. CS-0052135
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃Br₂NO
  • Molecular Weight 264.90
  • Synonym(s) 2,6-Dibromopyridine-3-carbaldehyde
  • SMILES O=CC1=CC=C(N=C1Br)Br

Description

2,6-Dibromonicotinaldehyde features a pyridine ring flanked by bromine substituents at the 2 and 6 positions, delivering a highly electron-deficient aldehyde moiety. This configuration enhances reactivity in cross-coupling processes while maintaining stability under standard handling conditions. The dibromo substitution pattern enables selective functionalization in synthetic sequences requiring orthogonal reactivity.

Application

2,6-Dibromonicotinaldehyde serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the 3- and 5-positions of the pyridine ring. Its aldehyde functionality facilitates imine formation and reductive amination, while the bromine substituents support palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Stille couplings. The molecule exhibits good bench stability and is compatible with standard purification techniques, making it suitable for use in medicinal chemistry campaigns and advanced synthetic sequences requiring orthogonally reactive handles.

Synthesis

  • Route1
    • In-stock
      2,6-Dibromopyridine|CS-W008833
      626-05-1
    • null|null
      107-31-3
    • ~%
    • In-stock
      2,6-Dibromonicotinaldehyde|CS-0052135
      55304-83-1

    References

    • WO2006/21848 A1, ; Page/Page column 30 ; WO 2006/021848 A1
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 66, # 20 p. 6775 - 6786

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   29.96
  • LogP   2.4191
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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