2-Fluoro-5-methylpyridine Chemical Properties

Boiling point:

158-159 °C (lit.)

Density 

1.072 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4730(lit.)

Flash point:

119 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.14±0.10(Predicted)

form 

Liquid

Specific Gravity

1.077

color 

Colorless to pale yellow

BRN 

107085

InChI

InChI=1S/C6H6FN/c1-5-2-3-6(7)8-4-5/h2-4H,1H3

InChIKey

AOSOZARHUJMBLZ-UHFFFAOYSA-N

SMILES

C1(F)=NC=C(C)C=C1

CAS DataBase Reference

2369-19-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36/37-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

Hazard Note 

Flammable/Irritant

HazardClass 

3

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:6-Fluoro-3-picoline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Fluoro-5-methylpyridine Usage And Synthesis

Chemical Properties

liquid

Synthesis

To a solution of 2-amino-5-methylpyridine (13) (20.0 g, 185 mmol) in fluoboric acid (50 wt% aqueous solution, 50 mL) was added sodium nitrite (16.6 g, 240 mmol) in batches at -10 °C while controlling the temperature of the reaction to be below 0 °C. After addition, the reaction mixture was stirred at 0 °C for 30 min, then warmed to 50 °C and continued stirring for 30 min. After completion of the reaction, the reaction was cooled to room temperature and the pH was adjusted to 9-10 with saturated aqueous sodium carbonate solution (250 mL), followed by extraction with dichloromethane (4 x 125 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by alumina column chromatography (eluent: dichloromethane) to afford 2-fluoro-5-methylpyridine (14) (7.50 g, 69 mmol) as a yellow oil in 37% yield. Thin-layer chromatography (TLC) analysis: Rf (Al2O3, dichloromethane) 0.92. Infrared spectra (IR, NaCl plate) νmax: 1246, 1379, 1486, 2929 cm-1. nuclear magnetic resonance hydrogen spectra (1H NMR, 200 MHz, CDCl3) δ: 2.25 (s, 3H, CH3), 6.75 (dd, 1H, J = 8.2 Hz, 3JH-F = 3.0 Hz, H-3), 7.52 (m, 1H, H-4), 7.94 (s, 1H, H-6). Nuclear magnetic resonance carbon spectrum (13C NMR, 50 MHz, CDCl3) δ: 17.4 (CH3), 108.8 (d, 2JC-F = 38Hz, C-3), 130.6 (C-5), 141.7 (d, 3JC-F = 8Hz, C-4), 147.2 (d, 3JC-F = 14Hz, C-6), 162.1 (d. 1JC-F = 236Hz, C-2).

References

[1] Journal of Fluorine Chemistry, 2005, vol. 126, # 3, p. 345 - 348
[2] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 818 - 838
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 1125
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1667 - 1675
[5] Patent: US5583148, 1996, A

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