ChemicalBook--->CAS DataBase List--->31181-53-0

31181-53-0

31181-53-0 Structure

31181-53-0 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
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
Spectrum DetailBack Directory
[Spectrum Detail]

5-Fluoro-2-methylpyridine(31181-53-0)1HNMR
5-Fluoro-2-methylpyridine(31181-53-0)19FNMR
5-Fluoro-2-methylpyridine(31181-53-0)FT-IR
Hazard InformationBack 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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