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2-Phenylisonicotinic acid

  • CAS No. 55240-51-2

  • Cat. No. CS-0067958
  • Molecule weight199.21
  • Purity≥98%
  • MDL No.MFCD03086008

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

2-Phenylisonicotinic acid|CS-0067958

Structure of 55240-51-2

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General Information

  • CAS No. 55240-51-2
  • Cat. No. CS-0067958
  • Purity ≥98%
  • MDL No. MFCD03086008
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₉NO₂
  • Molecular Weight 199.21
  • Synonym(s) 2-Phenyl-4-pyridinecarboxylic acid
  • SMILES O=C(C1=CC(C2=CC=CC=C2)=NC=C1)O

Description

2-Phenylisonicotinic acid features a rigid, planar architecture with orthogonal aromatic rings that enhance conjugation and electronic delocalization. This structural rigidity supports applications in ligand design and pharmaceutical scaffolding where defined spatial orientation is critical.

Application

2-Phenylisonicotinic acid serves as a versatile building block in medicinal chemistry, enabling the construction of biologically active heterocyclic scaffolds. Its ortho-phenyl substitution enhances rigidity and modulates electronic properties, facilitating efficient coupling reactions in amide bond formation and transition-metal-catalyzed transformations. The carboxylic acid functionality provides reliable handle for derivatization, while the compound exhibits good bench stability and ease of purification—ideal for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • Jansen, Koen; Heirbaut, Leen; Verkerk, Robert; Cheng, Jonathan D.; Joossens, Jurgen; Cos, Paul; Maes, Louis; Lambeir, Anne-Marie; De Meester, Ingrid; Augustyns, Koen; Van Der Veken, Pieter Journal of Medicinal Chemistry, 2014 , vol. 57, # 7 p. 3053 - 3074
  • Route2

    References

    • KONINKLIJKE PHILIPS ELECTRONICS N.V. Patent: WO2007/4113 A2, 2007 ; Location in patent: Page/Page column 24 ;
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 17 p. 5498 - 5502

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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