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CS-W001157 4
Total: USD 88.00

2-Bromo-6-(hydroxymethyl)pyridine

  • CAS No. 33674-96-3

  • Cat. No. CS-D0981
  • Purity≥97%
  • MDL No.MFCD04039884

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

2-Bromo-6-(hydroxymethyl)pyridine|CS-D0981

Structure of 33674-96-3

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General Information

  • CAS No. 33674-96-3
  • Cat. No. CS-D0981
  • Purity ≥97%
  • MDL No. MFCD04039884
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO
  • Molecular Weight 188.02
  • Synonym(s) 6-Bromopyridine-2-methanol
  • SMILES OCC1=NC(Br)=CC=C1

Description

2-Bromo-6-(hydroxymethyl)pyridine features a strategically positioned hydroxymethyl group that enables direct functionalization in late-stage synthesis. The bromine atom serves as a reactive handle for palladium-catalyzed couplings, while the pyridine ring provides a polar, nitrogen-containing scaffold ideal for medicinal chemistry applications. This compound demonstrates excellent stability under standard bench conditions and facilitates efficient access to substituted heterocycles through orthogonal transformations.

Application

2-Bromo-6-(hydroxymethyl)pyridine serves as a versatile building block for pyridine-based heterocycles, enabling direct functionalization at the 2-position via palladium-catalyzed cross-coupling. The hydroxymethyl group provides a handle for oxidation to carboxylic acid, reduction to alcohol, or derivatization into aldehyde intermediates. Its bench-stable nature and compatibility with diverse reaction conditions facilitate efficient synthesis of pharmaceutical scaffolds and ligands in medicinal chemistry workflows.

Synthesis

  • Route1
    • In-stock
      2,5-Dibromopyridine|CS-W001991
      624-28-2
    • null|null
      68-12-2
    • ~94%
    • In-stock
      2-Bromo-6-(hydroxymethyl)pyridine|CS-D0981
      33674-96-3

    References

    • WO2009/120789 A1, ; Page/Page column 80; 81 ;
  • Route2

    References

    • Tetrahedron, , vol. 57, # 7 p. 1175 - 1182
  • Route3
    • In-stock
      2,6-Dibromopyridine|CS-W008833
      626-05-1
    • null|null
      68-12-2
    • ~95%
    • In-stock
      2-Bromo-6-(hydroxymethyl)pyridine|CS-D0981
      33674-96-3

    References

    • European Journal of Organic Chemistry, , # 8 p. 1552 - 1558

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   33.12
  • LogP   1.3364
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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