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CS-W001157 4
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2-Phenylpyridin-3-ol

  • CAS No. 3308-02-9

  • Cat. No. CS-0156481
  • Molecule weight171.20
  • Purity≥97%
  • MDL No.None

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

2-Phenylpyridin-3-ol|CS-0156481

Structure of 3308-02-9

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General Information

  • CAS No. 3308-02-9
  • Cat. No. CS-0156481
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₉NO
  • Molecular Weight 171.20
  • Synonym(s) 5-21-03-00482 (Beilstein Handbook Reference)
  • SMILES C1=CC=C(C=C1)C2=C(C=CC=N2)O

Description

2-Phenylpyridin-3-ol features a rigid, planar architecture with a phenolic hydroxyl group positioned ortho to the pyridine nitrogen. This arrangement enables strong intramolecular hydrogen bonding, enhancing stability and influencing coordination behavior in transition metal complexes. The electron-rich pyridine ring facilitates π-stacking interactions, while the phenyl substituent contributes to extended conjugation. This compound serves as a key ligand scaffold in photophysical applications and catalytic systems requiring robust chelation.

Application

2-Phenylpyridin-3-ol serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles through palladium-catalyzed cross-coupling and cyclization reactions. Its ortho-hydroxypyridine motif provides strong chelation potential for transition metals, enhancing catalytic efficiency in C–H functionalization processes. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1
    • null|null
      1000414-79-8
    • ~16%
    • In-stock
      2-Phenylpyridin-3-ol|CS-0156481
      3308-02-9
    • null|null
      271588-24-0

    References

    • European Journal of Organic Chemistry, , # 23 p. 4041 - 4049
  • Route2

    References

    • US2003/87925 A1, ; US 20030087925 A1
  • Route3

    References

    • Ali; McKillop; Mitchell; Rebelo; Wallbank Tetrahedron, 1992 , vol. 48, # 37 p. 8117 - 8126

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   33.12
  • LogP   2.4542
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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