6-Azauracil Chemical Properties

Melting point:

274-275 °C(lit.)

Boiling point:

211.75°C (rough estimate)

Density 

1.5988 (rough estimate)

refractive index 

1.4264 (estimate)

storage temp. 

Store below +30°C.

solubility 

1 M NH4OH: 50mg/mL, clear to slightly hazy, colorless to light yellow-green

pka

7.78±0.20(Predicted)

form 

Fine Crystalline Powder

color 

White to light yellow

Water Solubility 

Partly soluble in water, ethanol, DMSO, and 1 M NH4OH (50 mg/ml).

BRN 

116472

InChI

InChI=1S/C3H3N3O2/c7-2-1-4-6-3(8)5-2/h1H,(H2,5,6,7,8)

InChIKey

SSPYSWLZOPCOLO-UHFFFAOYSA-N

SMILES

N1=CC(=O)NC(=O)N1

CAS DataBase Reference

461-89-2(CAS DataBase Reference)

NIST Chemistry Reference

1,2,4-Triazine-3,5(2H,4H)-dione(461-89-2)

EPA Substance Registry System

1,2,4-Triazine-3,5(2H,4H)-dione (461-89-2)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-63-25

Safety Statements 

26-36-45-38-36/37/39

WGK Germany 

3

RTECS 

XY7700000

F 

10-23

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29336980

MSDS

• Language:English Provider:1,2,4-Triazine-3,5-dione
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Azauracil Usage And Synthesis

Chemical Properties

white to light yellow fine crystalline powder

Uses

6-Azauracil (6-AU) is used as a growth inhibitor of various microorganisms via depletion of intracellular GTP and UTP nucleotide pools. 6-Azauracil has been widely used in investigations on modulation of transcription, especially in yeast models.

Definition

ChEBI: 6-azauracil is a 1,2,4-triazine compound having oxo-substituents at the 3- and 5-positions. It has a role as an antimetabolite. It is a member of 1,2,4-triazines and a nucleobase analogue.

Synthesis Reference(s)

The Journal of Organic Chemistry, 23, p. 1522, 1958 DOI: 10.1021/jo01104a033

Biochem/physiol Actions

6-Azauracil (6-AU) is a pyrimidine analog of uracil and exhibits antitumor activity. It inhibits the growth of various microorganisms by depleting intracellular guanosine triphosphate (GTP)?and uridine?triphosphate (UTP) nucleotide pools.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

The general procedure for the synthesis of 1,2,4-triazine-3,5(2H,4H)-dione from the compound (CAS: 928-73-4) was as follows: 2-[2-(aminocarbonyl)fluorenylidene] 33.9 g (0.259 mol) and 51 g (1.275 mol) of sodium hydroxide were accurately weighed and dissolved in 150 mL of ethylene glycol. The reaction mixture was stirred continuously for 12 hours at 80 °C using a magnetic stirrer. Upon completion of the reaction, the mixture was cooled to room temperature, 250 mL of methanol was added and allowed to stand for 12 hours to promote crystallization. Subsequent filtration was carried out to recover the solvent to give 41.9 g of wet product. The wet product was dissolved in 60 mL of ultrapure water and the pH of the solution was adjusted with concentrated hydrochloric acid to less than 3. The solution was heated to 80 °C and stirring was maintained for half an hour before it was rapidly cooled to 10 °C with ice brine. The precipitate was collected by filtration and washed well with ultrapure water. Finally, the product was dried under vacuum to give 18 g (0.159 mol, 61.6% yield) of 6-azauracil (CD-2).

Mode of action

6-Azauracil is a growth inhibitor effective on a variety of microorganisms. It functions by depleting the intracellular GTP and UTP nucleotide supply. Mutations in transcriptional elongation machinery, as well as mutations in a variety of other pathways, exaggerate the growth defect of cells in the presence of 6 AU.

References

[1] Patent: CN108440505, 2018, A. Location in patent: Paragraph 0089; 0102; 0103; 0104
[2] Journal of Organic Chemistry, 1958, vol. 23, p. 1522
[3] Chemische Berichte, 1947, vol. 80, p. 494,500
[4] Patent: US2003/69140, 2003, A1
[5] Journal of the Iranian Chemical Society, 2016, vol. 13, # 8, p. 1539 - 1547

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