50-71-5

Basic information

• Product Name: Alloxan
• Synonyms: ALLOXAN;2,4,5,6(1H,3H)-PYRIMIDINETETRONE;MESOXALYLUREA;MESOXALYLCARBAMIDE;,4,5,6-Pyrimidinetetrone;2,4,5,6-pyrimidintetron;2,4,5,6-Pyrimidintetrone;2,4,5,6-Tetraoxohexahydropyrimidine
• CAS NO: 50-71-5
• Molecular Formula: C₄H₂N₂O₄
• Molecular Weight: 142.07
• EINECS: 200-062-0
• Mol File: 50-71-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: ~245 °C (dec.)
• Boiling Point: 259.59°C (rough estimate)
• Flash Point: 201.4°C
• Appearance: white crystalline powder
• Density: 1.8588 (rough estimate)
• Vapor Pressure: 2.05E-08mmHg at 25°C
• Refractive Index: 1.4610 (estimate)
• Storage Temp.: 2-8°C
• PKA: pK (25°) 6.63
• Water Solubility: 8g/L(temperature not stated)
• CAS DataBase Reference: Alloxan(CAS DataBase Reference)
• NIST Chemistry Reference: Alloxan(50-71-5)
• EPA Substance Registry System: Alloxan(50-71-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 50-71-5(Hazardous Substances Data)

Usage

Chemical Properties

Alloxan is a white crystals, become pink on exposure to air; colorless aqueous solution which imparts pink color to skin. Soluble in water and alcohol.

Uses

Alloxan is used in biochemical research, cosmetics, organic synthesis.

Definition

ChEBI: A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.

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 dlabetes in experimental animals. Decomposes in storage to release CO2. Do not store in sealed container. Explodes when heated above 170℃. When heated to decomposition it emits toxic fumes of NOx,.

Purification Methods

Crystallisation from water gives the tetrahydrate. Anhydrous crystals are obtained by crystallisation from acetone, glacial acetic acid or by sublimation in vacuo. [See below and Beilstein 24 H 500, 24 I 428, 24 II 301, 24 III/IV 2137.]

InChI:InChI=1/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)

Synthetic route

BARBITURIC ACID (67-52-7) → 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5)

Conditions	Yield
With chromium(VI) oxide In acetic acid

3,5-dihydroxyphenol (108-73-6) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 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	Yield
With acetic acid at 20℃; for 24h;	92%

1,2-diamino-benzene (95-54-5) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → alloxazine (490-59-5)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	86%

benzyl (2-amino-3-(cyclohexylamino)phenyl)carbamate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → benzyl (10-cyclohexyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]-pteridine-6-yl)carbamate

Conditions	Yield
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 + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 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	Yield
With boron trioxide; acetic acid at 20℃; for 14h;	78%

pyrene‐4,5‐diamine + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → pyreno[4,5-g]pteridine-11,13(10H,12H)-dione

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	75%

2,3-Diaminonaphthalene (771-97-1) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → naphtho[2,3-g]pteridine-2,4(1H,3H)-dione (4794-65-4)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	73%

copper(II) choride dihydrate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → Cu(2+)*C4N2O4(2-)*3H2O=Cu(C4N2O4)*3H2O

Conditions	Yield
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) + cobalt(II) chloride (7646-79-9) → alloxane, Co-salt * pentahydrate

Conditions	Yield
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 + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → Ni(2+)*C4N2O4(2-)*5H2O=NiC4N2O4*5H2O

Conditions	Yield
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) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 8,9-difluoronaphtho[2,3-g]pteridine-2,4(1H,3H)-dione

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	58%

2,3-diaminephenazine (655-86-7) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → pteridino[6,7-b]phenazine-2,4(1H,3H)-dione

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	57%

1-(N-octylamino)-2-aminobenzene (38423-40-4) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 10-octylisoalloxazine

Conditions	Yield
With boric acid; acetic acid at 60℃; for 1h;	41%

N-butyl-4-trifluoromethylbenzene-1,2-diamine (320406-61-9) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 10-butyl-7-(trifluoromethyl)isoalloxazine

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

C26H30N4 + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → C30H28N6O2

Conditions	Yield
With boric acid; acetic acid at 60℃; for 1h;	33.7%

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) + 2,3-diaminomaleonitrile (18514-52-8) → 2,4-dioxo-1,2,3,4-tetrahydropteridine-6,7-dicarbonitrile (55408-53-2)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	32%

mercury(II) nitrate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → alloxane*mercury(II) oxide*7H2O

Conditions	Yield
With H2O In water pptn. from alloxane soln. with Hg(NO3)2;;

ferric sulfate nonahydrate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → Fe(OH)(SO4H)2(NH(CO)3NH(CO))H2O

Conditions	Yield
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;

Upstream product

• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 67-52-7 BARBITURIC ACID 

Downstream Products

• 490-59-5 alloxazine 
• 21708-43-0 10-benzylbenzo[g]pteridine-2,4(3H,10H)-dione 

Relevant articles and documents

Role of alloxan radical in generation of hydroxyl radical by reaction of alloxan with glutathione in the presence of Fe3+-ethylenediaminetetraacetic acid

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