4-Chloro-6-fluoroquinoline Chemical Properties

Melting point:

75.0 to 79.0 °C

Boiling point:

259.9±20.0 °C(Predicted)

Density 

1.366±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.90±0.16(Predicted)

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C9H5ClFN/c10-8-3-4-12-9-2-1-6(11)5-7(8)9/h1-5H

InChIKey

CKTQPWIDUQGUGG-UHFFFAOYSA-N

SMILES

N1C2C(=CC(F)=CC=2)C(Cl)=CC=1

CAS DataBase Reference

391-77-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41-37/38

Safety Statements 

26-39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933499090

MSDS

• Language:English Provider:ALFA

4-Chloro-6-fluoroquinoline Usage And Synthesis

Application

4-Chloro-6-fluoroquinoline is an organic synthesis intermediate and a pharmaceutical intermediate that can be used in laboratory research and development processes as well as in chemical and pharmaceutical synthesis.

Synthesis

General procedure for the synthesis of 4-chloro-6-fluoroquinoline from 6-fluoro-2,3-dihydroquinolin-4(1H)-one: 412.55 mL of phosphoryl chloride, 11.5 g of iodine, and 165.0 g of manganese dioxide were added to a four-necked flask fitted with a stirrer and heated under stirring to 50 °C. Subsequently, 660 mL of a dichloroethane solution containing 165.02 g of 6-fluoro-2,3-dihydroquinolin-4(1H)-one was slowly added dropwise. After completion of the dropwise addition, the reaction mixture was refluxed for 2 hours. After completion of the reaction, the dichloroethane solvent was removed by distillation under reduced pressure. The residue was neutralized to pH 5-6 with cold aqueous sodium bicarbonate and filtered. The filter cake was washed with water to neutral and finally dried under vacuum to give 154.22 g of light gray solid 4-chloro-6-fluoroquinoline in 85.0% yield.

References

[1] Patent: CN106565602, 2017, A. Location in patent: Paragraph 0008; 0024; 0025; 0026; 0027

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