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CS-W001157 4
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2-Phenylpyridine-3-carboxylic acid

  • CAS No. 33421-39-5

  • Cat. No. CS-0060518
  • Molecule weight199.21
  • Purity≥98%
  • MDL No.None

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

2-Phenylpyridine-3-carboxylic acid|CS-0060518

Structure of 33421-39-5

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General Information

  • CAS No. 33421-39-5
  • Cat. No. CS-0060518
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₉NO₂
  • Molecular Weight 199.21
  • Synonym(s) 2-Phenylnicotinic acid
  • SMILES C1=CC=C(C=C1)C2=NC=CC=C2C(=O)O

Description

2-Phenylpyridine-3-carboxylic acid features a rigid, planar architecture integrating an electron-deficient pyridine core with a phenyl ring and a carboxylic acid group. This combination enables strong coordination to metal centers, making it valuable in constructing luminescent complexes and functional materials.

Application

2-Phenylpyridine-3-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling efficient construction of bioactive heterocycles. Its carboxylic acid functionality facilitates direct amidation, esterification, and coupling reactions under standard conditions. The ortho-phenylpyridine motif provides structural rigidity and favorable π-stacking interactions, enhancing target binding affinity in kinase inhibitors and other pharmaceutical scaffolds. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step syntheses requiring functional group compatibility and predictable reactivity.

Synthesis

  • Route1

    References

    • DuPriest, Mark T.; Schmidt, Charles L.; Kuzmich, Daniel; Williams, Stanly B Journal of Organic Chemistry, 1986 , vol. 51, # 11 p. 2021 - 2023
  • Route2
    • 2-Phenylpyridine-3-carbonitrile|CS-0209452
      39065-49-1
    • ~99%
    • In-stock
      2-Phenylpyridine-3-carboxylic acid|CS-0060518
      33421-39-5

    References

    • Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch Jr., Joseph J.; McMasters, Daniel R.; Yan, Youwei Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2282 - 2293
  • Route3
    • 3-Pyridinecarbonitrile, 2-chloro-|CS-0654103
      6602-54-6
    • ~%
    • In-stock
      2-Phenylpyridine-3-carboxylic acid|CS-0060518
      33421-39-5

    References

    • Journal of Medicinal Chemistry, , vol. 48, # 7 p. 2282 - 2293

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   50.19
  • LogP   2.4468
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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