6-Fluoroquinaldine Chemical Properties

Melting point:

49-53 °C (lit.)

Boiling point:

99 °C / 3mmHg

Density 

1.1465 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in Chloroform.

pka

5.16±0.43(Predicted)

form 

powder to crystal

color 

White to Almost white

BRN 

1281677

CAS DataBase Reference

1128-61-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

38-41-36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29334990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Fluoroquinaldine Usage And Synthesis

Chemical Properties

brown powder or granules

Uses

Metal-free transfer hydrogenation of 6-fluoro-2-methylquinoline by employing several chiral Br?nsted acid catalysts was carried out in combination with dihydropyridines as the hydride source in asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation. Hydrogenation product of 6-fluoro-2-methylquinoline is the key intermediate of the antibacterial agent.

Uses

Quinoline derivative as a highly potent thrombin receptor antagonist

Synthesis

General procedure for the synthesis of 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline from 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline: 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (0.50 mmol), FeCl2 (1.9 mg, 1.5 × 10-2 mmol), DMSO (31.2 mg, 0.4 mmol) and p-xylene (1 mL). The reaction mixture was stirred using a balloon at 110 °C and oxygen atmosphere and the progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was cooled to room temperature and purified by fast chromatography (eluent: hexane-ethyl acetate, 10:1) to afford the target product 6-fluoro-2-methylquinoline in 70% yield. 6-fluoro-2-methylquinoline was a colorless oil.1H NMR (400 MHz, CDCl3): δ = 8.93 (m, 1H), 8.10 (m, 1H) , 7.64 (d, J=4.0 Hz, 1H), 7.54 (m, 1H), 7.43-7.35 (m, 2H), 2.82 (s, 3H).13C NMR (100 MHz, CDCl3): δ=149.2, 147.3, 137.1, 136.3, 129.6, 128.3, 126.3, 125.9. 120.8, 18.2. HRMS: m/z calculated value of [C10H9FN+H]+: 144.0813; measured value: 144.0813.

References

[1] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12224 - 12227
[2] Angew. Chem., 2016, vol. 128, # 40, p. 12412 - 12415,4
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 6983 - 6987
[4] Ross. Khim. Zh., 2013, vol. 125, # 27, p. 7121 - 7125,5
[5] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10652 - 10658

6-Fluoroquinaldine(1128-61-6)Related Product Information

• 6-FLUORO-4-HYDROXY-2-(TRIFLUOROMETHYL)QUINOLINE
• 4-CHLORO-6-FLUOROQUINALDINE
• 4-CHLORO-6-FLUORO-2-(TRIFLUOROMETHYL)QUINOLINE
• 6-FLUORO-4-HYDROXY-2-METHYLQUINOLINE
• Brequinar
• 6-Fluoroquinaldine
• 4-CHLORO-8-FLUOROQUINALDINE
• 4-CHLORO-7-FLUOROQUINALDINE
• 8-Fluoro-2-Methyl-Quinoline
• 7-FLUOROQUINALDINE
• 2-FLUORO-7,8,9,10-TETRAHYDRO-6H-CYCLOHEPTA[B]QUINOLINE-11-CARBOXYLIC ACID
• 6,8-difluoro-2-methylquinolin-4-ol
• 7-FLUORO-1,2,3,4-TETRAHYDRO-ACRIDINE-9-CARBOXYLIC ACID
• 6-FLUORO-4-HYDRAZINO-2-METHYLQUINOLINE
• 6-FLUORO-2-METHYLQUINOLINE-4-CARBOXYLIC ACID
• AURORA KA-4989
• AURORA KA-4991
• 4-CHLORO-6-FLUORO-2-TRICHLOROMETHYLQUINOLINE