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6-Aminouracil
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Name

6-Aminouracil

 EINECS 212-854-3
CAS No. 873-83-6 Density 1.406 g/cm3
PSA 91.74000 LogP -0.77340
Solubility slightly soluble in water Melting Point ≥360 °C(lit.)
Formula C4H5N3O2 Boiling Point 580.4 °C at 760 mmHg
Molecular Weight 127.103 Flash Point 304.8 °C
Transport Information N/A Appearance cream to light brown crystalline powder
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 873-83-6 (6-Aminouracil) Hazard Symbols N/A
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-;

Article Data 52

6-Aminouracil Synthetic route

57-13-6

urea

105-34-0

methyl 2-cyanoacetate

873-83-6

4-Amino-2,6-dihydroxypyrimidine

Conditions
ConditionsYield
Stage #1: methyl 2-cyanoacetate With sodium In methanol at 20℃; for 0.5h;
Stage #2: urea In methanol for 2h; Reflux;		96.9%
105-56-6

ethyl 2-cyanoacetate

57-13-6

urea

873-83-6

4-Amino-2,6-dihydroxypyrimidine

Conditions
ConditionsYield
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%
584-08-7

potassium carbonate

105-56-6

ethyl 2-cyanoacetate

873-83-6

4-Amino-2,6-dihydroxypyrimidine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 70℃; for 2h;88%
372-09-8

cyanoacetic acid

57-13-6

urea

873-83-6

4-Amino-2,6-dihydroxypyrimidine

Conditions
ConditionsYield
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;
1004-40-6

6-Amino-2-thiouracil

873-83-6

4-Amino-2,6-dihydroxypyrimidine

Conditions
ConditionsYield
With potassium superoxide; 18-crown-6 ether for 1h; Ambient temperature;51%
1560-54-9

allyltriphenylphosphonium bromide

6-azido-2,4(1H,3H)pyrimidinedione

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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With chloroacetyl chloride In chloroform for 10h; Heating;A 12%
B 2%
1448-98-2

N-(aminocarbonyl)-2-cyano-acetamide

873-83-6

4-Amino-2,6-dihydroxypyrimidine

Conditions
ConditionsYield
With sodium hydroxide
With water at 120℃; im Rohr;
With sodium hydroxide
With sodium hydroxide
591-07-1

acetylurea

105-56-6

ethyl 2-cyanoacetate

873-83-6

4-Amino-2,6-dihydroxypyrimidine

Conditions
ConditionsYield
With sodium ethanolate
With sodium amide; xylene at 120 - 150℃;

6-Aminouracil Chemical Properties


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

6-Aminouracil Uses

 6-Aminouracil (CAS NO.873-83-6) is used as intermediate of caffeine theocin and SDM.

6-Aminouracil 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.

6-Aminouracil Consensus Reports

Reported in EPA TSCA Inventory.

6-Aminouracil 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

6-Aminouracil 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.

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