6-Fluoroquinoline Chemical Properties

Boiling point:

126°C/30mmHg(lit.)

Density 

1.209 g/mL at 25 °C

RTECS 

VB8370020

refractive index 

n20/D1.592

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

4.32±0.10(Predicted)

form 

Oil

color 

Clear Colorless

λmax

330nm(EtOH)(lit.)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933491090

6-Fluoroquinoline Usage And Synthesis

Uses

6-Fluoroquinoline, is a versatile building block used in the synthesis of various chemical compounds.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 7288, 1991 DOI: 10.1021/jo00026a019

Synthesis

General procedure for the synthesis of 6-fluoroquinoline from 6-fluoro-1,2,3,4-tetrahydroquinoline: To a 10 mL round-bottomed flask fitted with a magnetic stirring bar, 6-fluoro-1,2,3,4-tetrahydroquinoline (0.5 mmol), 40 wt% toluene solution (2.2 equiv., 1.1 mmol, 0.5 mL), and a DEAD solution of CHCl3 ( 1.0 mL). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was concentrated using a rotary evaporator. The residue was purified by column chromatography using EtOAc: hexane (1:5) as eluent to give 6-fluoroquinoline. For compounds 2f and 2m, the product spot was close to the spot of residual DEAD. To remove residual DEAD, 1 equivalent of PPh3 was added after the reaction and the reaction mixture was stirred for 10 min. Subsequently, the reaction mixture was concentrated using a rotary evaporator. The residue was purified by column chromatography using CHCl3: hexane (1:1) as eluent to give the final 6-fluoroquinoline.

References

[1] Organic Letters, 2015, vol. 17, # 18, p. 4404 - 4407
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 11, p. 3080 - 3084
[3] Angew. Chem., 2017, vol. 129, # 11, p. 3126 - 3130,5
[4] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[5] Synthetic Communications, 2018, vol. 48, # 11, p. 1291 - 1298

6-Fluoroquinoline(396-30-5)Related Product Information

• 6-fluoroquinoline-3-carbaldehyde
• 6-fluoroquinoline-2-carboxylic acid
• 6-FLUORO-4-HYDROXYQUINOLINE
• 6-FLUOROQUINOLINE-3-CARBOXYLIC ACID
• 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE
• 6-Fluoroquinoline-3-carboxylic acid ethyl ester
• ETHYL 6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE
• 6-FLUORO-4-HYDROXY-2-METHYLQUINOLINE
• 4-CHLORO-6-FLUORO-2-(TRIFLUOROMETHYL)QUINOLINE
• ETHYL 4-CHLORO-6,8-DIFLUOROQUINOLINE-3-CARBOXYLATE
• 6-FLUORO-4-HYDRAZINOQUINOLINE
• 6-FLUORO-4-HYDROXY-2-(TRIFLUOROMETHYL)QUINOLINE
• 4-CHLORO-6-FLUORO-2-METHYLQUINOLINE
• ETHYL 4-CHLORO-6-FLUOROQUINOLINE-3-CARBOXYLATE
• 6-Fluoroquinaldine
• ETHYL 8-CHLORO-6-FLUORO-4-HYDROXY-3-QUINOLINECARBOXYLATE
• 2-AMINO-6-FLUORO-3-METHYLQUINOLINE
• Ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate