3,6-difluoropyridin-2-aMine

3,6-difluoropyridin-2-aMine Property

Boiling point:

190.0±35.0 °C(Predicted)

Density 

1.393±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

0.57±0.10(Predicted)

Appearance

Off-white to gray Solid

InChI

InChI=1S/C5H4F2N2/c6-3-1-2-4(7)9-5(3)8/h1-2H,(H2,8,9)

InChIKey

HMRIDZSIODFQSH-UHFFFAOYSA-N

SMILES

C1(N)=NC(F)=CC=C1F

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3,6-difluoropyridin-2-aMine Chemical Properties,Usage,Production

Synthesis

Under argon protection, 2,3,6-trifluoropyridine (5 g, 37.59 mmol) was dissolved in 1,4-dioxane (20 mL) and stirred until completely dissolved. Subsequently, ammonia (20 mL) was slowly added to the solution. The reaction mixture was stirred continuously at 100 °C for 16 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming complete consumption of 2,3,6-trifluoropyridine, the reaction was quenched with cold water (500 mL). The reaction mixture was extracted with dichloromethane (2 x 500 mL) and the organic phases were combined. The organic phase was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 3,6-difluoropyridin-2-amine (3 g, 62% yield) as an off-white solid, which could be used for subsequent reactions without further purification.TLC conditions: 10% ethyl acetate/hexane (Rf: 0.5).

References

[1] Patent: WO2007/87549, 2007, A2. Location in patent: Page/Page column 117
[2] Patent: WO2015/109109, 2015, A1. Location in patent: Paragraph 0742
[3] Patent: US2017/44182, 2017, A1. Location in patent: Paragraph 1026