METHYL 5-FLUOROPYRIDINE-3-CARBOXYLATE Chemical Properties

Melting point:

48 °C

Boiling point:

194.5±25.0 °C(Predicted)

Density 

1.243±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

0.77±0.20(Predicted)

Appearance

White to off-white Solid

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37/39

HazardClass 

IRRITANT

HS Code 

29333990

METHYL 5-FLUOROPYRIDINE-3-CARBOXYLATE Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

Methyl 5-fluoronicotinate

Synthesis

Example 2.26: Synthesis of methyl 5-fluoronicotinate; To a stirring solution of 243 mg (1.6 mmol) of methyl 5-aminonicotinate dissolved in 5 mL of HF-pyridine at 0 °C was slowly added 119 mg (1.72 mmol) of sodium nitrite (NaNO2). The reaction mixture was stirred continuously at 0 °C for 30 min, then warmed up to 50 °C and kept for 1 hour. Upon completion of the reaction, the reaction was quenched with ice and saturated sodium bicarbonate (NaHCO3) solution. The aqueous phase was extracted with chloroform (CHCl3) and the organic phase was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated. Purification by fast silica gel column chromatography (eluent: 1% methanol/chloroform) afforded 139 mg of methyl 5-fluoronicotinate as a yellow solid in 56% yield.

References

[1] Patent: WO2006/110668, 2006, A1. Location in patent: Page/Page column 62
[2] Journal of Organic Chemistry, 1949, vol. 14, p. 328,331
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9896 - 9900
[4] Angew. Chem., 2018, vol. 130, p. 10044 - 10048,5

METHYL 5-FLUOROPYRIDINE-3-CARBOXYLATE(455-70-9)Related Product Information

• 2-Pyridinecarboxamide,5-fluoro-(9CI)
• 5-Fluoro-2-forMylpyridine
• 2-Pyridinecarboxylicacid,5-fluoro-,methylester(9CI)
• 3-FLUORO-5-FORMYLPYRIDINE
• 3-FLUORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE
• METHYL 2,6-DICHLORO-5-FLUORONICOTINATE
• 3-METHOXYPHENYL 2,6-DICHLORO-5-FLUORONICOTINATE
• Ethyl 2-chloro-5-fluoronicotinate
• ETHYL 5-FLUORONICOTINATE
• ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate
• 2-Butene-1,4-diol, bis(5-fluoronicotinate)
• 2,6-DIMETHYLPHENYL 2,6-DICHLORO-5-FLUORONICOTINATE
• METHYL2-CHLORO-5-FLUORONICOTINATE
• METHYL 5-FLUOROPYRIDINE-3-CARBOXYLATE
• PHENYL 2,6-DICHLORO-5-FLUORONICOTINATE