| Identification | More | [Name]
6-Aminouracil | [CAS]
873-83-6 | [Synonyms]
4(6)-AMINOURACIL
4-ADHP
4-AMINO-2,6-DIHYDROXYPYRIMIDINE
4-AMINOURACIL
6-AMINO-2,4-DIHYDROXY-PYRIMIDINE
6-AMINO-2,4-PYRIMIDINEDIOL
6-AMINOPYRIMIDINE-2,4(1H,3H)-DIONE
6-AMINOPYRIMIDINE-2,4-DIOL
6-AMINOURACIL
AKOS 92815
AURORA KA-377
TIMTEC-BB SBB000054
3h)-pyrimidinedione,6-amino-4(1h
4-Amimouracil
6-amino-uraci
4-Amino-2,6-dihydroxypyrimidine~4-Aminouracil
Aminouracil
4-Amino-2,6-dihydroxypyrimidine
6-Amino-2,4-pyrimidinediol
6-Aminouracil
6-Aminouracil
6-Amino-2,4-pyrimidinediol
4-AMINO-2-6-DIHYDROXY-PYRIMIDINECRYSTALL INE
4-AMINOURACI | [EINECS(EC#)]
212-854-3 | [Molecular Formula]
C4H5N3O2 | [MDL Number]
MFCD00006071 | [Molecular Weight]
127.1 | [MOL File]
873-83-6.mol |
| Chemical Properties | Back Directory | [Appearance]
cream to light brown crystalline powder | [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 | [Detection Methods]
HPLC,NMR | [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]
873-83-6(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P280f | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
YQ8750000
| [F ]
10-23 | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29335995 | [Storage Class]
11 - Combustible Solids | [Toxicity]
LDLo par-mus: 2400 mg/kg CBCCT* 7,696,55 |
| Hazard Information | Back Directory | [Chemical Properties]
cream to light brown crystalline powder | [Uses]
6-Aminouracil is used as an intermediate in pharmaceuticals such as caffeine, theophylline, and SDM. | [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 |
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