3-Pyridinemethanamine,6-fluoro-(9CI) Chemical Properties

Boiling point:

63-65 °C(Press: 0.56 Torr)

Density 

1.180±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

7.73±0.29(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H7FN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H,3,8H2

InChIKey

KYRWSLUCAPNJPI-UHFFFAOYSA-N

SMILES

C1=NC(F)=CC=C1CN

Safety Information

HS Code 

2933399990

3-Pyridinemethanamine,6-fluoro-(9CI) Usage And Synthesis

Uses

6-Fluoro-3-pyridinemethanamine is a useful compound for the study of herbicidal activity of 2-cyano-3-[[(6-fluoro-3-pyridinyl)methyl]amino]acrylates.

Synthesis

General procedure for the synthesis of (6-fluoropyridin-3-yl)methanamine from 6-fluoro-3-cyanopyridine: 6-fluoro-3-cyanopyridine (300 mg, 2.46 mmol) was dissolved in 2 mol/L ammonia/methanol solution (30 mL), nickel Ruanne (0.5 g) was added at room temperature and the reaction was carried out for 12 h under hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth and washed with methanol (5 mL x 2). The filtrate was concentrated to dryness and the residue was purified by silica gel column chromatography (eluent ratio of dichloromethane: methanol = 100:4) to give 262 mg of yellow oily solid in 85% yield.

References

[1] Patent: CN106916101, 2017, A. Location in patent: Paragraph 0149; 0150
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 19, p. 7965 - 7983

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