6-BROMO-[1,8]NAPHTHYRIDIN-2-OL Chemical Properties

Melting point:

>300℃

Boiling point:

415.9±45.0 °C(Predicted)

Density 

1.711

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

9.93±0.20(Predicted)

Appearance

Light yellow to light brown Solid

Water Solubility 

Insoluble in water.

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22-41-37/38

Safety Statements 

22-26-36/37/39-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

6-BROMO-[1,8]NAPHTHYRIDIN-2-OL Usage And Synthesis

Uses

6-Bromo-1,8-naphthyridin-2(1H)-one is used as an organic chemical synthesis intermediate.

Synthesis

Tert-butyl 3-(2-amino-5-bromopyridin-3-yl)acrylate (2.5 g, 8.35 mmol) was dissolved in anhydrous methanol (50 mL) and sodium methanolate (8.5 mL, 4.9 M solution, 41.75 mmol) was added. The reaction mixture was heated to reflux for 2 hours and subsequently cooled to room temperature. The mixture was cooled in an ice water bath and water (100 mL) was added with vigorous stirring to precipitate. The solid was collected by filtration and washed with water (20 mL). The filtrate was neutralized with 1 M aqueous hydrochloric acid, precipitated again, filtered and washed with water (20 mL). The solids obtained twice were combined and dried under reduced pressure to give the off-white target product 6-bromo-1,8-naphthyridin-2(1H)-one (1.75 g, 93% yield). The product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 8.43 (d, 1H, J=2.5Hz), 8.06 (d, 1H, J=2.5Hz), 7.60 (d, 1H, J=9.1Hz), 6.44 (d, 1H, J=9.1Hz); ESIMS m/z 225 (100%), 227 (100%) ) [C8H5N2OBr + H]+.

References

[1] Patent: WO2007/53131, 2007, A2. Location in patent: Page/Page column 203
[2] Patent: WO2015/186137, 2015, A1. Location in patent: Page/Page column 16

6-BROMO-[1,8]NAPHTHYRIDIN-2-OL(72754-05-3)Related Product Information

• 6-BROMO-[1,8]NAPHTHYRIDIN-2-OL
• 3-Bromo-1,8-naphthyridine