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CS-W001157 4
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6-Phenylnicotinic acid

  • CAS No. 29051-44-3

  • Cat. No. CS-0145812
  • Purity≥98%
  • MDL No.MFCD03086128

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

6-Phenylnicotinic acid|CS-0145812

Structure of 29051-44-3

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General Information

  • CAS No. 29051-44-3
  • Cat. No. CS-0145812
  • Purity ≥98%
  • MDL No. MFCD03086128
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₉NO₂
  • Molecular Weight 199.21
  • Synonym(s) None
  • SMILES O=C(C1=CC=C(C2=CC=CC=C2)N=C1)O

Description

6-Phenylnicotinic acid is a functionalized nicotinic acid derivative featuring a phenyl group at the 6-position, enabling direct integration into bioactive scaffolds. This aryl-substituted pyridine carboxylic acid offers enhanced π-stacking potential and metabolic stability, facilitating its use in medicinal chemistry campaigns targeting receptor modulators and kinase inhibitors under standard bench conditions.

Application

6-Phenylnicotinic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles and pharmaceutical scaffolds. Its ortho-substituted pyridine core offers enhanced metabolic stability and favorable binding interactions. The carboxylic acid functionality facilitates direct derivatization or coupling reactions, while the phenyl group provides structural rigidity and π-stacking potential. This compound exhibits excellent bench stability and compatibility with standard synthetic protocols, making it well-suited for iterative library construction and process-scale applications.

Synthesis

  • Route1

    References

    • Steunenberg, Peter; Ruggi, Albert; Van Den Berg, Nynke S.; Buckle, Tessa; Kuil, Joeri; Van Leeuwen, Fijs W.B.; Velders, Aldrik H. Inorganic Chemistry, 2012 , vol. 51, # 4 p. 2105 - 2114
  • Route2

    References

    • Merck and Co., Inc. Patent: US5872136 A1, 1999 ;
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    References

    • Coteron, Jose M.; Catterick, David; Castro, Julia; Chaparro, Maria J.; Diaz, Beatriz; Fernandez, Esther; Ferrer, Santiago; Gamo, Francisco J.; Gordo, Mariola; Gut, Jiri; De Las Heras, Laura; Legac, Jennifer; Marco, Maria; Miguel, Juan; Munoz, Vicente; Porras, Esther; De La Rosa, Juan C.; Ruiz, Jose R.; Sandoval, Elena; Ventosa, Pilar; Rosenthal, Philip J.; Fiandor, Jose M. Journal of Medicinal Chemistry, 2010 , vol. 53, # 16 p. 6129 - 6152

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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