8-BROMOXANTHINE

8-BROMOXANTHINE Property

Melting point:

>297°C (dec.)

Density 

2.118±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO, Methanol

form 

Solid

pka

6.87±0.70(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C5H3BrN4O2/c6-4-7-1-2(8-4)9-5(12)10-3(1)11/h(H3,7,8,9,10,11,12)

InChIKey

ZFQWSCZYQLPFFZ-UHFFFAOYSA-N

SMILES

N1C2=C(NC(=O)NC2=O)NC=1Br

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

8-BROMOXANTHINE Chemical Properties,Usage,Production

Uses

8-Bromoxanthine is used to study Arsenite-​inhibited xanthine oxidase.

Uses

8-Bromoxanthine is used to study Arsenite-?inhibited xanthine oxidase.

Synthesis

General procedure for the synthesis of 8-bromo-1H-purine-2,6(3H,7H)-dione using 1H-purine-2,6(3H,7H)-dione as a raw material: weigh 15g of 1H-purine-2,6(3H,7H)-dione in a 250mL reaction flask, add 250mL of deionized water, and stir until complete dissolution. 7.6 mL of liquid bromine was added slowly dropwise, and the rate of dropwise acceleration was controlled to avoid violent reaction. The reaction mixture was heated to 100 °C and stirring was maintained until the color of the reaction solution faded completely from the red color of the bromine, indicating that the reaction was complete. The heating was stopped and the reaction mixture was cooled to room temperature. The reaction mixture was washed with a small amount of ice water to remove unreacted bromine. Subsequently, the reaction mixture was diafiltered and the solid product was collected. The filter cake was dried in a vacuum drying oven to give 18.4 g of 8-bromo-1H-purine-2,6(3H,7H)-dione.

References

[1] Justus Liebigs Annalen der Chemie, 1883, vol. 221, p. 344
[2] Patent: CN103172633, 2016, B. Location in patent: Paragraph 0145-0147