Product Name

  • Name

    Alloxan

  • EINECS 200-062-0
  • CAS No. 50-71-5
  • Article Data2
  • CAS DataBase
  • Density 1.681g/cm3
  • Solubility
  • Hazard Symbols UN NO.
  • Synonyms Alloxan(8CI); 2,4,5,6-Pyrimidinetetrone; 2,4,5,6-Tetraoxohexahydropyrimidine;Alloxane; Mesoxalylcarbamide; Mesoxalylurea; NSC 7169; Pyrimidinetetrone
  • PSA 129.26000
  • LogP -1.67810

Synthetic route

BARBITURIC ACID
67-52-7

BARBITURIC ACID

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

Conditions
ConditionsYield
With chromium(VI) oxide In acetic acid
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

5-hydroxy-5-[2,4,6-trihydroxy-3,5-bis(5-hydroxy-2,4,6-trioxo-3,5-dihydro-1H-pyrimidin-5-yl)phenyl]-3,5-dihydro-1H-pyrimidine-2,4,6-trione

5-hydroxy-5-[2,4,6-trihydroxy-3,5-bis(5-hydroxy-2,4,6-trioxo-3,5-dihydro-1H-pyrimidin-5-yl)phenyl]-3,5-dihydro-1H-pyrimidine-2,4,6-trione

Conditions
ConditionsYield
With acetic acid at 20℃; for 24h;92%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

alloxazine
490-59-5

alloxazine

Conditions
ConditionsYield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;86%
benzyl (2-amino-3-(cyclohexylamino)phenyl)carbamate

benzyl (2-amino-3-(cyclohexylamino)phenyl)carbamate

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

benzyl (10-cyclohexyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]-pteridine-6-yl)carbamate

benzyl (10-cyclohexyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]-pteridine-6-yl)carbamate

Conditions
ConditionsYield
With boron trioxide; acetic acid at 20℃; for 18h;82%
dibenzyl ((((1‘‘R,2‘‘R)-cyclohexane-1‘‘,2‘‘-diyl)bis(azanediyl))bis(2-amino-3,1-phenylene))dicarbamate

dibenzyl ((((1‘‘R,2‘‘R)-cyclohexane-1‘‘,2‘‘-diyl)bis(azanediyl))bis(2-amino-3,1-phenylene))dicarbamate

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

dibenzyl (((1‘‘R,2‘‘R)-cyclohexane-1‘‘,2‘‘-diyl)bis(2,4-dioxo-2,3,4,4a-tetrahydrobenzo[g]pteridine-9a,6-diyl))dicarbamate

dibenzyl (((1‘‘R,2‘‘R)-cyclohexane-1‘‘,2‘‘-diyl)bis(2,4-dioxo-2,3,4,4a-tetrahydrobenzo[g]pteridine-9a,6-diyl))dicarbamate

Conditions
ConditionsYield
With boron trioxide; acetic acid at 20℃; for 14h;78%
pyrene‐4,5‐diamine

pyrene‐4,5‐diamine

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

pyreno[4,5-g]pteridine-11,13(10H,12H)-dione

pyreno[4,5-g]pteridine-11,13(10H,12H)-dione

Conditions
ConditionsYield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;75%
2,3-Diaminonaphthalene
771-97-1

2,3-Diaminonaphthalene

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

naphtho[2,3-g]pteridine-2,4(1H,3H)-dione
4794-65-4

naphtho[2,3-g]pteridine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;73%
copper(II) choride dihydrate

copper(II) choride dihydrate

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

Cu(2+)*C4N2O4(2-)*3H2O=Cu(C4N2O4)*3H2O

Cu(2+)*C4N2O4(2-)*3H2O=Cu(C4N2O4)*3H2O

Conditions
ConditionsYield
With water In water gradual addn. of an aq. soln. of CuCl2*2H2O to an aq. soln. of alloxane; simultaneous addn. of 10% aq. NaOH (->pH=7.5); pH=5 or pH=6 for a few hours;; ppt.; washing with cold H2O; drying in vac. at ambient temp. over CaCl2;;72%
With H2O In water gradual addn. of an aq. soln. of CuCl2*2H2O to an aq. soln. of alloxane; simultaneous addn. of 10% aq. NaOH (->pH=7.5); pH=5 or pH=6 for a few hours;; ppt.; washing with cold H2O; drying in vac. at ambient temp. over CaCl2;;72%
5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

cobalt(II) chloride
7646-79-9

cobalt(II) chloride

alloxane, Co-salt * pentahydrate

alloxane, Co-salt * pentahydrate

Conditions
ConditionsYield
With sodium hydroxide In water addition of CoCl2 in H2O to a solution of alloxane in H2O under addition of NaOH-solution until pH=7.5; then pH=5-6; seperation of the ppt. after some hours;; washing the product with cold H2O; drying in vac. at normal temperature over CaCl2;;69%
With NaOH In water
nickel(II) nitrate hexahydrate

nickel(II) nitrate hexahydrate

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

Ni(2+)*C4N2O4(2-)*5H2O=NiC4N2O4*5H2O

Ni(2+)*C4N2O4(2-)*5H2O=NiC4N2O4*5H2O

Conditions
ConditionsYield
With sodium hydroxide In water gradual addn. of equimolar amt. of aq. Ni(NO3)2*6H2O soln. to aq. soln. of alloxan, addn. of 10% NaOH soln. to pH 7.5, then adjusting to pH 5-6;; pptn., sepg. after several hours, washing with cold H2O, drying in vac. at ambient temp. over CaCl2;;66%
2-amino-4,5-difluoroaniline
76179-40-3

2-amino-4,5-difluoroaniline

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

8,9-difluoronaphtho[2,3-g]pteridine-2,4(1H,3H)-dione

8,9-difluoronaphtho[2,3-g]pteridine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;58%
2,3-diaminephenazine
655-86-7

2,3-diaminephenazine

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

pteridino[6,7-b]phenazine-2,4(1H,3H)-dione

pteridino[6,7-b]phenazine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;57%
1-(N-octylamino)-2-aminobenzene
38423-40-4

1-(N-octylamino)-2-aminobenzene

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

10-octylisoalloxazine

10-octylisoalloxazine

Conditions
ConditionsYield
With boric acid; acetic acid at 60℃; for 1h;41%
N-butyl-4-trifluoromethylbenzene-1,2-diamine
320406-61-9

N-butyl-4-trifluoromethylbenzene-1,2-diamine

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

10-butyl-7-(trifluoromethyl)isoalloxazine

10-butyl-7-(trifluoromethyl)isoalloxazine

Conditions
ConditionsYield
With boric acid; acetic acid at 70℃; for 3h;39%
C26H30N4

C26H30N4

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

C30H28N6O2

C30H28N6O2

Conditions
ConditionsYield
With boric acid; acetic acid at 60℃; for 1h;33.7%
5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

2,3-diaminomaleonitrile
18514-52-8

2,3-diaminomaleonitrile

2,4-dioxo-1,2,3,4-tetrahydropteridine-6,7-dicarbonitrile
55408-53-2

2,4-dioxo-1,2,3,4-tetrahydropteridine-6,7-dicarbonitrile

Conditions
ConditionsYield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;32%
mercury(II) nitrate

mercury(II) nitrate

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

alloxane*mercury(II) oxide*7H2O

alloxane*mercury(II) oxide*7H2O

Conditions
ConditionsYield
With H2O In water pptn. from alloxane soln. with Hg(NO3)2;;
ferric sulfate nonahydrate

ferric sulfate nonahydrate

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
50-71-5

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione

Fe(OH)(SO4H)2(NH(CO)3NH(CO))H2O

Fe(OH)(SO4H)2(NH(CO)3NH(CO))H2O

Conditions
ConditionsYield
In water mixing ratio Fe2(SO4)3*9H2O:alloxan = 1:2 at pH=2; evapd. (water bath); sepn. of crystals; dried; elem.anal.; X-ray diffraction;

Alloxan Chemical Properties


IUPAC Name: 1,3-diazinane-2,4,5,6-tetrone 
Molecular Weight: 142.06968 g/mol
Molecular Formula: C4H2N2O4 
Density: 1.681 g/cm3 
Melting Point: ~245 °C (dec.)
Boiling Point: 409.5 °C at 760 mmHg 
Flash Point: 201.4 °C
Index of Refraction: 1.519
Molar Refractivity: 25.66 cm3
Molar Volume: 84.5 cm3
Polarizability: 10.17*10-24 cm3
Surface Tension: 62.6 dyne/cm 
Enthalpy of Vaporization: 76.46 kJ/mol
Vapour Pressure: 2.05E-08 mmHg at 25 °C 
XLogP3-AA: -1
H-Bond Donor: 2
H-Bond Acceptor: 4
Tautomer Count: 5
Exact Mass: 142.001457
MonoIsotopic Mass: 142.001457
Topological Polar Surface Area: 92.3
Heavy Atom Count: 10
Complexity: 222
Canonical SMILES: C1(=O)C(=O)NC(=O)NC1=O
InChI: InChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)
InChIKey: HIMXGTXNXJYFGB-UHFFFAOYSA-N
EINECS: 200-062-0
Storage temp.: 2-8 °C

Alloxan History

 Alloxan (CAS NO.50-71-5) was originally isolated in 1818 by Brugnatelli and got its name in 1838 by Friedrich Wöhler and Justus von Liebig. The name "Alloxan" emerged from an amalgamation of the words "Allantoin" and "Oxalsäure" (oxaluric acid).

Alloxan Production

The original preparation for Alloxan (CAS NO.50-71-5) was by oxidation of uric acid by nitric acid. Alloxan is a strong oxidizing agent and it forms a hemiacetal with its reduced reaction product dialuric acid (in which a carbonyl group is reduced to a hydroxyl group) which is called alloxantin.

Alloxan Toxicity Data With Reference

1.    

eye-rbt 500 mg/24H MLD

     85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,862.
2.    

cyt-mus-ipr 50 mg/kg

     JOHEA8    Journal of Heredity. 65 (1974),345.
3.    

ipr-mus TDLo:200 mg/kg (female 8D post):TER

     JEEMAF    Journal of Embryology and Experimental Morphology. 14 (1965),63.
4.    

orl-rat LD50:5210 mg/kg

     28ZOAH    Chemicals in War Prentiss, A.M.,1972,150.
5.    

ivn-rat LD50:300 mg/kg

     CRSBAW    Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. 142 (1948),1335.
6.    

ipr-mus LDLo:300 mg/kg

     PSEBAA    Proceedings of the Society for Experimental Biology and Medicine. 67 (1948),154.
7.    

scu-mus LDLo:400 mg/kg

     PSEBAA    Proceedings of the Society for Experimental Biology and Medicine. 67 (1948),154.
8.    

ivn-mus LDLo:200 mg/kg

     PSEBAA    Proceedings of the Society for Experimental Biology and Medicine. 67 (1948),154.
9.    

ivn-rbt LDLo:300 mg/kg

     AJCPAI    American Journal of Clinical Pathology. 16 (1946),257.
10.    

rec-rbt LDLo:180 mg/kg

   &nbs

Alloxan Consensus Reports

Reported in EPA TSCA Inventory.

Alloxan Safety Profile

Poison by intraperitoneal, intravenous, subcutaneous, and rectal routes. Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Produces diabetes in experimental animals. Decomposes in storage to release CO2. Do not store in sealed container. Explodes when heated above 170°C. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: HarmfulXn
Risk Statements: 20/21/22-36/37/38
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
WGK Germany: 3
F: 8-10-23
Hazardous Substances Data: 50-71-5(Hazardous Substances Data)

Alloxan Specification

 Alloxan (CAS NO.50-71-5) is also called 2,4,5,6(1H,3H)-Pyrimidinetetrone ; Mesoxalylurea ; Mesoxalylcarbamide ; 4,5,6-Pyrimidinetetrone ; 2,4,5,6-Pyrimidintetron ; 2,4,5,6-Tetraoxohexahydropyrimidine . Alloxan (CAS NO.50-71-5) is a kind of pesticides. It's moderate toxic. It will explosive by heating above 170 °C. Alloxan (CAS NO.50-71-5) is also flammable. It will produce toxic nitrogen oxide fumes when buring. And it decomposits of carbon dioxide at room temperature. So the storage environment should be ventilate, low-temperature and dry. Keep Anthramycin (CAS NO.4803-27-4) separate from raw materials of food. Do not store in a sealed tank.

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