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CS-W001157 4
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5-Fluoro-2-hydroxypyridine

  • CAS No. 51173-05-8

  • Cat. No. CS-W009189
  • Purity≥98%
  • MDL No.MFCD03092918

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

5-Fluoro-2-hydroxypyridine|CS-W009189

Structure of 51173-05-8

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General Information

  • CAS No. 51173-05-8
  • Cat. No. CS-W009189
  • Purity ≥98%
  • MDL No. MFCD03092918
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄FNO
  • Molecular Weight 113.09
  • Synonym(s) uoro-2-hydroxypyridine
  • SMILES O=C1C=CC(F)=CN1

Description

5-Fluoro-2-hydroxypyridine features a strategically positioned fluorine atom and a hydroxyl group on the pyridine scaffold, enabling enhanced reactivity in nucleophilic substitution and metal-catalyzed coupling processes. This electron-deficient heterocycle serves as a key building block for bioactive compounds and functional materials.

Application

5-Fluoro-2-hydroxypyridine serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C2 position via nucleophilic substitution or transition-metal-catalyzed coupling. Its hydroxyl group offers orthogonal reactivity for derivatization, while the fluorine substituent enhances metabolic stability and modulates electronic properties. The compound exhibits good bench stability and facilitates efficient synthesis of pyridine-based scaffolds relevant to API development.

Synthesis

  • Route1

    References

    • Ueda, Yasutsugu; Connolly, Timothy P.; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao; Chen, Chung-Pin H.; Yeung, Kap-Sun; Zhang, Zhongxing; Leahy, David Kenneth; Pack, Shawn K.; Soundararajan, Nachimuthu; Sirard, Pierre; Levesque, Kathia; Thoraval, Dominique Patent: US2005/209246 A1, 2005 ; Location in patent: Page/Page column 30; 31 ;
  • Route2

    References

    • Regueiro-Ren, Alicia; Xue, Qiufen M.; Swidorski, Jacob J.; Gong, Yi-Fei; Mathew, Marina; Parker, Dawn D.; Yang, Zheng; Eggers, Betsy; D'Arienzo, Celia; Sun, Yongnian; Malinowski, Jacek; Gao, Qi; Wu, Dedong; Langley, David R.; Colonno, Richard J.; Chien, Caly; Grasela, Dennis M.; Zheng, Ming; Lin, Pin-Fang; Meanwell, Nicholas A.; Kadow, John F. Journal of Medicinal Chemistry, 2013 , vol. 56, # 4 p. 1656 - 1669

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   32.86
  • LogP   0.514
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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