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| CAS No.: | 873-83-6 |
|---|---|
| Name: | 6-Aminouracil |
| Article Data: | 52 |
| Cas Database | |
| Molecular Structure: | |
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| Formula: | C4H5N3O2 |
| Molecular Weight: | 127.103 |
| Synonyms: | Uracil,6-amino- (6CI,7CI,8CI);2,4-Dihydroxy-6-aminopyrimidine;4-Amino-2,6-dihydroxypyrimidine;6-Amino-2,4-dihydroxypyrimidine;6-Amino-2,4-dioxo-1,2,3,4-tetrahydropyrimidine;6-Aminopyrimidine-2,4(1H,3H)-dione;6-Aminopyrimidine-2,4-diol;2,4(1H,3H)-Pyrimidinedione,6-amino-; |
| EINECS: | 212-854-3 |
| Density: | 1.406 g/cm3 |
| Melting Point: | ≥360 °C(lit.) |
| Boiling Point: | 580.4 °C at 760 mmHg |
| Flash Point: | 304.8 °C |
| Solubility: | slightly soluble in water |
| Appearance: | cream to light brown crystalline powder |
| Safety: | 22-24/25 |
| PSA: | 91.74000 |
| LogP: | -0.77340 |
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| Conditions | Yield |
|---|---|
| Stage #1: methyl 2-cyanoacetate With sodium In methanol at 20℃; for 0.5h; Stage #2: urea In methanol for 2h; Reflux; | 96.9% |
| Conditions | Yield |
|---|---|
| With ethanol; sodium for 3h; Heating; | 95% |
| Stage #1: ethyl 2-cyanoacetate With sodium In methanol at 20℃; for 0.5h; Stage #2: urea In methanol for 3h; Reflux; | 95.2% |
| With sodium In ethanol Reflux; | 69% |
| Conditions | Yield |
|---|---|
| With hydrazine hydrate In ethanol at 70℃; for 2h; | 88% |
| Conditions | Yield |
|---|---|
| With acetic anhydride; sodium hydroxide In neat (no solvent) for 0.166667h; Microwave irradiation; | 78% |
| With acetic anhydride und Behandeln des Reaktionsprodukts mit wss.NaOH; | |
| With acetic anhydride at 60℃; for 3h; |
| Conditions | Yield |
|---|---|
| With potassium superoxide; 18-crown-6 ether for 1h; Ambient temperature; | 51% |
- 1560-54-9
allyltriphenylphosphonium bromide
A
- 873-83-6
4-Amino-2,6-dihydroxypyrimidine
B
- 65996-50-1
2,4-Dioxo-1,2,3,4-tetrahydropyrrolo<3,2-d>pyrimidine
| Conditions | Yield |
|---|---|
| Stage #1: allyltriphenylphosphonium bromide With lithium hydride In butanone at 20℃; Stage #2: 6-azido-2,4(1H,3H)pyrimidinedione for 2h; Heating; | A 26% B 36% |
- 52386-29-5
6-amino-2-methoxy-3H-4-pyrimidone
- 79-04-9
chloroacetyl chloride
A
- 873-83-6
4-Amino-2,6-dihydroxypyrimidine
B
- 130056-78-9
6-amino-5-(α-chloroacetyl)-3,4-dihydro-2-methoxy-4-oxopyrimidine
| Conditions | Yield |
|---|---|
| In chloroform for 10h; Heating; | A 12% B 2% |
- 52386-29-5
6-amino-2-methoxy-3H-4-pyrimidone
A
- 873-83-6
4-Amino-2,6-dihydroxypyrimidine
B
- 130056-78-9
6-amino-5-(α-chloroacetyl)-3,4-dihydro-2-methoxy-4-oxopyrimidine
| Conditions | Yield |
|---|---|
| With chloroacetyl chloride In chloroform for 10h; Heating; | A 12% B 2% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide | |
| With water at 120℃; im Rohr; | |
| With sodium hydroxide | |
| With sodium hydroxide |
| Conditions | Yield |
|---|---|
| With sodium ethanolate | |
| With sodium amide; xylene at 120 - 150℃; |
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Chemistry
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IUPAC Name: 6-Amino-1H-pyrimidine-2,4-dione
Molecular Formula: C4H5N3O2
Molecular Weight: 127.10 g/mol
SMILES: n1c(O)cc(nc1O)N
InChI: InChI=1/C4H5N3O2/c5-2-1-3(8)7-4(9)6-2/h1H,(H4,5,6,7,8,9)
EINECS: 212-854-3
Product Categories: PYRIMIDINE; Pyridines, Pyrimidines, Purines and Pteredines; Amines; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides
Melting Point: >=360 °C(lit.)
Water Solubility: slightly soluble
Index of Refraction: 1.544
Molar Refractivity: 28.55 cm3
Molar Volume: 90.3 cm3
Polarizability: 11.32×10-24 cm3
Surface Tension: 50.5 dyne/cm
Density: 1.406 g/cm3
Flash Point: 304.8 °C
Enthalpy of Vaporization: 90.04 kJ/mol
Boiling Point: 580.4 °C at 760 mmHg
Vapour Pressure of 6-Aminouracil (CAS NO.873-83-6): 4.52E-14 mmHg at 25 °C
Uses
6-Aminouracil (CAS NO.873-83-6) is used as intermediate of caffeine theocin and SDM.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | oral | 1250mg/kg (1250mg/kg) | Pharmaceutical Chemistry Journal Vol. 30, Pg. 320, 1996. | |
| mouse | LDLo | parenteral | 2400mg/kg (2400mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 696, 1955. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS of 6-Aminouracil (CAS NO.873-83-6): YQ8750000
Specification
6-Aminouracil (CAS NO.873-83-6), its Synonyms are 2,4(1H,3H)-Pyrimidinedione, 6-amino- ; 4-Amino-2,6-dihydroxylpyrimidine ; 4-Amino-2,6-dihydroxypyrimidine ; 4-Amino-2,6-dioxypyrimidine ; 4-Amino-2,6-pyrimidinediol ; 4-Aminouracil ; 6-Amino-2,4-dihydroxypyrimidine ; 6-Amino-2,4-pyrimidinediol ; Uracil, 6-amino- ; Uracil, 6-amino- (VAN) (8CI) . It is cream to light brown crystalline powder.