3003. 5-Diazouracil

Nomenclature

CAS number: 2435-76-9
5-Diazo-2,4(1H,3H)-pyrimidinedione; DU; 2,4-dioxo-5-diazopyrimidine; 5-diazo-2,4-dioxopyrimidine.
C4H2N4O2; mol wt 138.08.
C 34.79%, H 1.46%, N 40.58%, O 23.17%.

Description and references

Prepd by diazotization of 5-aminouracil: Johnson et al., Ber. 64, 2629 (193l). Revised structure: Thurber, Townsend, J. Heterocycl. Chem. 9, 629 (1972). Has significant activity against gram-positive and gram-negative bacteria in vivo: Hunt, Pittillo, Appl. Microbiol. 16, 1792 (1968).

Chemical structure

Properties

Crystals, conflagrates at 198°. The stout prisms obtained from ice water should be white, not yellow or red. Sensitive to light, temp and air. Best stored in evacuated, refrigerated ampuls. Acid reactions. IR spectrum: Band at 4.57 μ. Forms alcoholates, also a red monohydrate, C4H4N4O3, from which a potassium salt, KC4H3N4O3, is obtained which is slightly sol in water with neutral reaction.

Use

In cancer research.