4-Amino-6-bromoquinoline Chemical Properties

Melting point:

228-230°C

Boiling point:

388.7±27.0 °C(Predicted)

Density 

1.649±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

8.21±0.50(Predicted)

Appearance

White to yellow Solid

Safety Information

Hazard Codes 

T

Risk Statements 

25-36

Safety Statements 

26-45

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933499090

4-Amino-6-bromoquinoline Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-amino-6-bromoquinoline from 6-bromo-4-chloroquinoline was as follows: 6-bromo-4-chloroquinoline (500 mg, 2.1 mmol), acetamide (2.438 g, 41.3 mmol), and potassium carbonate (1.449 g, 10.5 mmol) were added to a reaction flask fitted with a magnetic stirrer. The reaction mixture was heated to 180 °C and maintained at this temperature for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with water (50 mL). The aqueous phase was extracted with ethyl acetate (20 mL × 3), the organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol = 20:1) to afford the target product 6-bromoquinolin-4-amine (198 mg, 43% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6) and LC-MS (ESI) to confirm its structure.1H NMR (400 MHz, DMSO-d6) δ 8.46 (d, J = 2.2 Hz, 1H), 8.25 (d, J = 7.2 Hz, 1H), 7.95 (dd, J = 8.9, 2.3 Hz, 1H), 7.69 (d, J = 8.9, 2.3 Hz, 1H), 7.69 (d, J = 8.9, 2.3 Hz, 1H), 7.95 (dd, J = 8.9, 2.3 Hz, 2.3 Hz, 1H) 7.69 (d, J = 8.9 Hz, 1H), 7.12 (d, J = 7.2 Hz, 1H), 5.64 (s, 2H). LC-MS (ESI) m/z = 223.1, 225.1 (M + H, M + 2 + H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1919 - 1922

4-Amino-6-bromoquinoline(65340-73-0)Related Product Information

• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• Isoquinoline
• 2-Bromoquinoline
• quinolinium hydrogen sulphate
• Quinhydrone
• 4-Aminoguinoline
• Bis(2-ethylhexyl)amine
• ALTRENOGEST
• 6-Bromoquinoline
• Quinclorac
• Glycine
• Ethoxyquin
• Triallylamine
• 8-Bromoquinoline
• 8-Hydroxyquinoline
• Tris(hydroxymethyl)aminomethane
• 4-AMINO-8-BROMOQUINOLINE
• 2-AMINO-4-BROMOQUINOLINE