5-Fluoro-2-methylpyridine Chemical Properties

Boiling point:

135-136 C

Density 

1.077g/ml

storage temp. 

under inert gas (nitrogen or Argon) at 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 Information

Hazard Codes 

T,Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

2933399990

5-Fluoro-2-methylpyridine Usage And Synthesis

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

5-Fluoro-2-methylpyridine(31181-53-0)Related Product Information

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