| Identification | More | [Name]
5-Fluoro-2-methylpyridine | [CAS]
31181-53-0 | [Synonyms]
3-FLUORO-6-METHYLPYRIDINE
3-FLUORO-6-PICOLINE
5-FLUORO-2-METHYLPYRIDINE
5-FLUORO-2-PICOLINE
2-methyl-5-fluoro-pyridine
3-FLUORO-6-METHYLPYRIDINE (3-FLUORO-6-PICOLINE)
5-FLUORO-2-METHYLPYRIDINE (5-FLUORO-2-PICOLINE)
5-FLUORO-2-PICOLINE5-FLUORO-2-METHYLPYRIDINE | [Molecular Formula]
C6H6FN | [MDL Number]
MFCD03095271 | [Molecular Weight]
111.12 | [MOL File]
31181-53-0.mol |
| Chemical Properties | Back Directory | [Boiling point ]
135-136 C | [density ]
1.077g/ml | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
liquid | [pka]
3.53±0.10(Predicted) | [color ]
Clear, almost colourless | [InChI]
InChI=1S/C6H6FN/c1-5-2-3-6(7)4-8-5/h2-4H,1H3 | [InChIKey]
LXAHHHIGZXPRKQ-UHFFFAOYSA-N | [SMILES]
C1(C)=NC=C(F)C=C1 | [CAS DataBase Reference]
31181-53-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H227-H302-H315-H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [Hazard Codes ]
T,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Synthesis]
5-Amino-2-methyl pyridine (2.8 g, 25.9 mmol) was added to a mixture of water (15 mL) and cone. HCl (7 mL) and cooled to 0°C. NaNO2 (3.5 g, 51.8 mmol) was added portion-wise with stirring over 10 min whilst keeping the reaction temperature between -5℃ and O℃. After stirring for 10 min 60 % w/w HPF6 (14 mL) was added dropwise with cooling, at which point a precipitate formed. This was filtered, washed with cold water and diethyl ether and dried. The solid was then heated slowly to 100℃; the reaction being very exothermic. After 5 min a dark red oily material formed which was then cooled to r.t. The oil was basifed with dilute sodium hydroxide to pH ~10 and extracted with dichloromethane. The combined organics were dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by column chromatography over neutral alumina using 20 % dichloromethane-petroleum ether to yield 5-fluoro-2- methyl pyridine (1.57 g, 55%) as an oil.
| [References]
[1] Patent: WO2008/62182, 2008, A1. Location in patent: Page/Page column 161
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1970 - 1977
[3] Patent: WO2003/87098, 2003, A1. Location in patent: Page/Page column 95-96
[4] Tetrahedron Letters, 2010, vol. 51, # 38, p. 5035 - 5037
[5] Patent: WO2018/15410, 2018, A1. Location in patent: Paragraph 0365-0368 |
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