6-METHOXY-8-NITROQUINOLINE Chemical Properties

Melting point:

158-160 °C(lit.)

Boiling point:

342.67°C (rough estimate)

Density 

1.3244 (rough estimate)

refractive index 

1.5910 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

1.25±0.20(Predicted)

form 

Crystalline Powder

color 

Yellow

CAS DataBase Reference

85-81-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-40

Safety Statements 

26-27-36/37/39

WGK Germany 

3

RTECS 

VC0365000

HS Code 

29334900

MSDS

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

6-METHOXY-8-NITROQUINOLINE Usage And Synthesis

Chemical Properties

YELLOW CRYSTALLINE POWDER

Uses

6-Methoxy-8-nitroquinoline is used in treating and preventing pancreatic cancer. Also, used in preparation of Quinoline derivatives as antiparasitic agents useful in the prophylaxis and treatment of malaria and parasitic diseases.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1569, 1946 DOI: 10.1021/ja01212a057
Organic Syntheses, Coll. Vol. 3, p. 568, 1955

Synthesis

4-Methoxy-2-nitroaniline (20.0 g, 119 mmol) was mixed with glycerol (34.0 g, 369 mmol), 3-nitrobenzenesulfonic acid sodium salt (24.0 g, 107 mmol), water (25 mL), and concentrated sulfuric acid (34 mL), and the reaction was carried out at reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to 45 °C, slowly poured into 1 L of cold water and stirred vigorously with dichloromethane (500 mL) for 30 min. The resulting two-phase solution was filtered through diatomaceous earth and the aqueous phase was extracted with dichloromethane (3 x 300 mL). The organic phases were combined, washed sequentially with water (400 mL) and saturated saline (400 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to remove the solvent. The crude product was purified by silica gel column chromatography with hexane/ethyl acetate (4/1, v/v) as eluent to afford 6-methoxy-8-nitroquinoline (10.0 g, 49.0 mmol, 42% yield) as a brown solid. Mass spectrum (electrospray ionization) m/z 205 ([M+H]+).

References

[1] Patent: US2003/32645, 2003, A1

6-METHOXY-8-NITROQUINOLINE(85-81-4)Related Product Information

• 6-Methylquinoline
• 8-Aminoisoquinoline
• 3-Nitrophenol
• 6-Hydroxyquinoline
• 6-METHOXY-8-NITROQUINOLINE
• 8-Nitroquinoline
• 6-Methoxyquinoline
• 8-AMINO-6-METHOXYQUINOLINE
• 3-Nitroanisole
• 3-Aminophenol
• 2-Amino-6-methoxypyridine
• 4-Methyl-6-methoxy-8-nitroquinoline
• 8-METHOXY-6-NITROQUINOLINE
• 8-METHOXY-5-NITROQUINOLINE
• 4-METHOXY-6-NITROQUINOLINE
• 7-Methoxy-8-nitroquinoline
• 6-METHOXY-5-NITROQUINOLINE
• 3-Bromo-6-Methoxy-8-Nitroquinoline