6-Aminouracil Chemical Properties

Melting point:

≥360 °C(lit.)

Boiling point:

235.85°C (rough estimate)

Density 

1.4748 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly, Heated), Methanol (Slightly)

form 

Crystalline Powder

pka

3.76±0.10(Predicted)

color 

Cream to light brown

Water Solubility 

slightly soluble

BRN 

120491

InChI

InChI=1S/C4H5N3O2/c5-2-1-3(8)7-4(9)6-2/h1H,(H4,5,6,7,8,9)

InChIKey

LNDZXOWGUAIUBG-UHFFFAOYSA-N

SMILES

C1(=O)NC(N)=CC(=O)N1

CAS DataBase Reference

873-83-6(CAS DataBase Reference)

EPA Substance Registry System

2,4(1H,3H)-Pyrimidinedione, 6-amino- (873-83-6)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

YQ8750000

F 

10-23

TSCA 

Yes

HS Code 

29335995

Toxicity

LDLo par-mus: 2400 mg/kg CBCCT* 7,696,55

MSDS

• Language:English Provider:4-Amino-2,6-dihydroxypyrimidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Aminouracil Usage And Synthesis

Chemical Properties

cream to light brown crystalline powder

Definition

ChEBI: 6-aminouracil is a pyrimidone.

Safety Profile

Moderately toxic by parenteralroute. When heated to decomposition it emits toxic fumesof NOx.

Synthesis

GENERAL METHOD: Ethyl cyanoacetate (0.1 mol) was mixed with urea, methylurea and/or methylthiourea (0.1 mol) in anhydrous ethanol (290 mL) containing sodium. The reaction mixture was refluxed for 10-12 hours and subsequently cooled to room temperature. Acidification was carried out by adjusting the pH to 6 with acetic acid. The resulting precipitate was washed with distilled water and dried in a desiccator overnight.1a was obtained in 69% yield with a melting point over 360°C (literature value ≥ 360°C).

Purification Methods

Purify the aminouracil by dissolving it in 3M aqueous NH3, filtering hot, and adding 3M formic acid until precipitation is complete. Cool, filter off (or centrifuge), wash well with cold H2O, then EtOH and dry it in air. Dry it further in a vacuum at ~80o. [Barlin & Pfeiderer J Chem Soc (B) 1424 1971, Beilstein 25 III/IV 4107.]

References

[1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 7, p. 1053 - 1055
[2] Journal of Chemical Research, 2016, vol. 40, # 12, p. 771 - 777
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 662 - 668
[4] Australian Journal of Chemistry, 2007, vol. 60, # 2, p. 120 - 123
[5] Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1281 - 1292

6-Aminouracil (873-83-6)Related Product Information

• 4,6-Dihydroxypyrimidine
• Lithium diisopropylamide
• Sulfamic acid
• 4-Aminopyrimidine
• Iminodiacetonitrile
• ALTRENOGEST
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• Triclosan
• Acetaminophen
• Betaine
• Uracil
• Glucosamine
• 4,4'-Diaminodiphenylsulfone
• 4-Hydroxy-6-aminopyrimidine
• Iminodiacetic acid
• 4-Aminoantipyrine
• N,N-Dimethyl-1,4-phenylenediamine
• EC 2.6.1.2