| Identification | More | [Name]
2-Fluoro-5-methylpyridine | [CAS]
2369-19-9 | [Synonyms]
2-FLUORO-5-METHYLPYRIDINE
2-FLUORO-5-PICOLINE
6-FLUORO-3-PICOLINE
Fluoromethylpyridine3
2-FLUORO-5-METHYLPYRIDINE 99%
2-Fluoro-5-methylpyridine/2-Fluoro-5-Picoline
2-Fluoro-5-methylpyridine97%
2-FLUORO-5-METHYPYRIDINE
2-Fluoro-5-methylpyridine ,99% | [EINECS(EC#)]
624-867-5 | [Molecular Formula]
C6H6FN | [MDL Number]
MFCD00041225 | [Molecular Weight]
111.12 | [MOL File]
2369-19-9.mol |
| Chemical Properties | Back Directory | [Boiling point ]
158-159 °C (lit.) | [density ]
1.072 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4730(lit.)
| [Fp ]
119 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [form ]
Liquid | [pka]
-0.14±0.10(Predicted) | [color ]
Colorless to pale yellow | [Specific Gravity]
1.077 | [Detection Methods]
HPLC | [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 Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [Hazard Note ]
Flammable/Irritant | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [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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