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6-Aminouracil

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6-Aminouracil Basic information
Product Name:6-Aminouracil
Synonyms:4(6)-AMINOURACIL;6-AMINO-2,4-PYRIMIDINEDIOL;6-AMINO-2,4-DIHYDROXY-PYRIMIDINE;6-AMINOURACIL;6-AMINOPYRIMIDINE-2,4(1H,3H)-DIONE;AURORA KA-377;4-AMINOURACIL;4-AMINO-2,6-DIHYDROXYPYRIMIDINE
CAS:873-83-6
MF:C4H5N3O2
MW:127.1
EINECS:212-854-3
Product Categories:Amines;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Aromatics;Heterocycles;88/kg;bc0001
Mol File:873-83-6.mol
6-Aminouracil Structure
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)
pKa3.76±0.10(Predicted)
form Crystalline Powder
color Cream to light brown
Water Solubility slightly soluble
BRN 120491
InChIInChI=1S/C4H5N3O2/c5-2-1-3(8)7-4(9)6-2/h1H,(H4,5,6,7,8,9)
InChIKeyLNDZXOWGUAIUBG-UHFFFAOYSA-N
SMILESC1(=O)NC(N)=CC(=O)N1
CAS DataBase Reference873-83-6(CAS DataBase Reference)
EPA Substance Registry System2,4(1H,3H)-Pyrimidinedione, 6-amino- (873-83-6)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
RTECS YQ8750000
10-23
TSCA TSCA listed
HS Code 29335995
Storage Class11 - Combustible Solids
ToxicityLDLo par-mus: 2400 mg/kg CBCCT* 7,696,55
MSDS Information
ProviderLanguage
4-Amino-2,6-dihydroxypyrimidine English
ACROS English
SigmaAldrich English
ALFA English
6-Aminouracil Usage And Synthesis
Chemical Propertiescream to light brown crystalline powder
DefinitionChEBI: 6-aminouracil is a pyrimidone.
Safety ProfileModerately toxic by parenteralroute. When heated to decomposition it emits toxic fumesof NOx.
Synthesis
Ethyl cyanoacetate

105-56-6

Urea

57-13-6

6-Aminouracil

873-83-6

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 MethodsPurify 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 Preparation Products And Raw materials
Raw materials1,4-Dioxane-->Urea-->Ethyl cyanoacetate-->Cyanoacetic acid-->Sodium-->Ethanol
Preparation Products6-methyl-1H-Pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione
Tag: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