6-FLUORO-1,2,3,4-TETRAHYDROQUINOLINE Chemical Properties

Melting point:

32-34℃

Boiling point:

248.0±29.0 °C(Predicted)

Density 

1.107±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

5.15±0.20(Predicted)

Appearance

Off-white to light brown <32°C Solid,>34°C Liquid

CAS DataBase Reference

59611-52-8

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

HS Code 

2933499090

6-FLUORO-1,2,3,4-TETRAHYDROQUINOLINE Usage And Synthesis

Uses

6-Fluoro-1,2,3,4-tetrahydroquinoline is used as pharmaceutical intermediate.

Synthesis

A THF solution of 6-fluoro-3,4-dihydroquinolin-2(1H)-one (6.0 g, 36.36 mmol) was slowly added to a THF (80 mL) suspension of LiAlH4 (2.76 g, 72.73 mmol) under stirring conditions. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium chloride solution and ethyl acetate and filtered through diatomaceous earth. The filtrate was diluted with ethyl acetate and washed sequentially with water and saturated sodium chloride solution and the organic phase was dried with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 4.5 g (81% yield) of 6-fluoro-1,2,3,4-tetrahydroquinoline as a brown liquid.1H NMR (400 MHz, CDCl3): δ 6.65-6.78 (m, 2H), 6.37-6.40 (m, 1H), 3.26 (t, J=5.3 Hz, 2H), 2.73 (t, J=6.6 Hz, 2H), 1.88-1.94 (m, 2H).

References

[1] Patent: WO2017/142883, 2017, A1. Location in patent: Paragraph 0183; 0186
[2] Patent: WO2014/78813, 2014, A1. Location in patent: Page/Page column 141

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