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CS-W001157 4
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Imidazo[1,2-a]pyridine-6-carboxylic acid

  • CAS No. 139022-25-6

  • Cat. No. CS-W005545
  • Purity≥98%
  • MDL No.MFCD07021498

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

Imidazo[1,2-a]pyridine-6-carboxylic acid|CS-W005545

Structure of 139022-25-6

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General Information

  • CAS No. 139022-25-6
  • Cat. No. CS-W005545
  • Purity ≥98%
  • MDL No. MFCD07021498
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆N₂O₂
  • Molecular Weight 162.15
  • Synonym(s) H-imidazo[1,2-a]pyridine-6-carboxylic acid
  • SMILES O=C(C1=CN2C(C=C1)=NC=C2)O

Description

Imidazo[1,2-a]pyridine-6-carboxylic acid features a fused heterocyclic core with a carboxylic acid group at the 6-position, enabling direct conjugation or derivatization. This scaffold combines enhanced planarity and electron-deficient character with improved solubility compared to related systems, making it valuable for medicinal chemistry and materials development.

Application

Imidazo[1,2-a]pyridine-6-carboxylic acid serves as a versatile heterocyclic building block in medicinal chemistry, enabling the synthesis of bioactive scaffolds through standard amide coupling and derivatization protocols. The carboxylic acid functionality facilitates direct conjugation with amines, supports salt formation for improved solubility, and enables further functionalization via esterification or activation. Its rigid, planar structure enhances binding affinity in target-directed drug discovery, while the bench-stable nature simplifies handling and purification in routine synthetic workflows.

Synthesis

  • Route1
    • Imidazo[1,2-a]pyridine-6-carboxylic acid hydrochloride|CS-0183268
      1314777-15-5
    • ~77%
    • In-stock
      Imidazo[1,2-a]pyridine-6-carboxylic acid|CS-W005545
      139022-25-6

    References

    • GENENTECH,INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Kanl H.; DRAGOVICH, Peter; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; YUEN, Po-Wai; ZAK, Mark; ZHANG, Yamin; ZHENG, Xiaozhang; ZHAO, Guiling Patent: WO2013/127268 A1, 2013 ; Location in patent: Page/Page column 59; 60 ;
  • Route2
    • In-stock
      6-Aminonicotinic acid|CS-W016509
      3167-49-5
    • null|null
      2032-35-1
    • ~60%
    • In-stock
      Imidazo[1,2-a]pyridine-6-carboxylic acid|CS-W005545
      139022-25-6

    References

    • Rogers, Bruce N.; Piotrowski, David W.; Walker, Daniel Patrick; Jacobsen, Eric Jon; Acker, Brad A.; Wishka, Donn G.; Groppi JR., Vincent E. Patent: US2003/236264 A1, 2003 ; Location in patent: Page 52 ;
  • Route3

    References

    • Li, Qun; Woods, Keith W.; Claiborne, Akiyo; Gwaltney, Ii, Stephen L.; Barr, Kenneth J.; Liu, Gang; Gehrke, Laura; Credo; Hui, Yu Hua; Lee, Jang; Warner, Robert B.; Kovar, Peter; Nukkala, Michael A.; Zielinski, Nicolette A.; Tahir, Stephen K.; Fitzgerald, Michael; Kim, Ki H.; Marsh, Kennan; Frost, David; Ng, Shi-Chung; Rosenberg, Saul; Sham, Hing L. Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 3 p. 465 - 469

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

Quality Control

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Computational Chemistry Data

  • TPSA   54.6
  • LogP   1.0325
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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