ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Fluoropyridine 3-Fluoropyridine-4-carboxylic acid

3-Fluoropyridine-4-carboxylic acid

Product Name3-Fluoropyridine-4-carboxylic acid
CAS393-53-3
MFC6H4FNO2
MW141.1
EINECS639-266-3
MOL File393-53-3.mol

Chemical Properties

Melting point	251-254°C (dec.)
Boiling point	360.0±22.0 °C(Predicted)
Density	1.419±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
form	solid
pka	2.85±0.10(Predicted)
color	White to off-white
BRN	383678
InChI	1S/C6H4FNO2/c7-5-3-8-2-1-4(5)6(9)10/h1-3H,(H,9,10)
InChIKey	POLXLLIQWDBJMD-UHFFFAOYSA-N
SMILES	OC(=O)c1ccncc1F
CAS DataBase Reference	393-53-3(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,F
Risk Statements	36/37/38-10
Safety Statements	26-36-16
WGK Germany	3
HazardClass	IRRITANT
HS Code	2933399990
Storage Class	13 - Non Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Uses

3-Fluoropyridine-4-carboxylic acid reacts with MnCl2·4H2O in a mixed DMF/EtOH solvent at low concentration and elevated temperature to yield Mn3-MOF crystals[2]. As a CRAC channels blocker, 3-fluoropyridine-4-carboxylic acid is administered intraperitoneally at 1.5 mg/kg b.w. in long-term (14-day) therapy of ovalbumin-induced allergic asthma in guinea pigs[3][4].

Synthesis

124-38-9

393-53-3

3-Fluoropyridine (25 g, 257 mmol) was slowly added dropwise to a solution of tetrahydrofuran (600 mL) containing butyl lithium (270 mmol) and diisopropylamine (27.4 g, 271 mmol) at -78 °C. The reaction mixture was stirred continuously at this temperature for 1 hour. Subsequently, crushed dry ice was added to the reaction system and gradually warmed to room temperature over 1 hour. Upon completion of the reaction, the pH of the reaction solution was adjusted to 5 with an aqueous solution of hydrogen chloride and acidified. The resulting precipitate was collected by filtration and dried. The final 3-fluoroisonicotinic acid (25.2 g, 179 mmol, 70% yield) was obtained as colorless crystals.

References

[1] Patent: WO2006/36015, 2006, A2. Location in patent: Page/Page column 121-122
[2]Cheng, Z., Dong, L., Li, Y., Yan, H., Zhang, J., Xiang, S., & Zhang, Z. (2025). Lewis Acidity‐Enhanced Metal‐Organic Frameworks as High‐Efficiency Cathode Catalysts for Advanced Li‐CO<sub>2</sub> Batteries. Advanced Functional Materials, 35(35). https://doi.org/10.1002/adfm.202504330
[3]Sutovska, M., Kocmalova, M., Joskova, M., Adamkov, M., & Franova, S. (2015). The effect of long-term administered CRAC channels blocker on the functions of respiratory epithelium in guinea pig allergic asthma model. General physiology and biophysics, 34(02), 167–176. https://doi.org/10.4149/gpb_2014031
[4]Šutovská, M., Kocmálová, M., Adamkov, M., Výbohová, D., Mikolka, P., Mokrá, D., Hatok, J., & Fraňová, M. A. S. (2013). The long-term administration of Orai 1 antagonist possesses antitussive, bronchodilatory and anti-inflammatory effects in experimental asthma model. General physiology and biophysics, 32(02), 251–259. https://doi.org/10.4149/gpb_2013018

3-Fluoropyridine-4-carboxylic acid

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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