2244-11-3

Basic information

• Product Name: ALLOXAN MONOHYDRATE
• Synonyms: 2,4,5,6(1h,3h)-pyrimidinetetronehydrate;2,4,5,6-tetraoxohexahydropyrimidinehydrate;mesoxalylcarbamidemonohydrate;LABOTEST-BB LT00138148;MESOXALYLUREA;MESOXALYLUREA, MONOHYDRATE;2,4,5,6-TETRAOXYPYRIMIDINE;2,4,5,6-TETRAOXYPYRIMIDINE MONOHYDRATE
• CAS NO: 2244-11-3
• Molecular Formula: C₄H₂N₂O₄*4H₂O
• Molecular Weight: 160.08
• EINECS: 251-501-8
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Active Pharmaceutical Ingredients;buildingblock
• Mol File: 2244-11-3.mol

Chemical Properties

• Melting Point: 255 °C (dec.)(lit.)
• Boiling Point: 374.1 °C at 760 mmHg
• Flash Point: 180 °C
• Appearance: Off-white to beige-yellow/Crystalline Powder
• Vapor Pressure: 8.59E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: may be hazy yellow
• Water Solubility: Soluble in water, ethanol, acetone, glacial acetic acid and methanol. Slightly soluble in chloroform, petroleum ether, toluene,
• Sensitive: Air Sensitive
• Merck: 14,282
• BRN: 5309394
• CAS DataBase Reference: ALLOXAN MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLOXAN MONOHYDRATE(2244-11-3)
• EPA Substance Registry System: ALLOXAN MONOHYDRATE(2244-11-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-26-36/37
• WGK Germany: 3
• RTECS: UW0492000
• TSCA: Yes
• Hazardous Substances Data: 2244-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Alloxan Monohydrate is used as a cytotoxic compound in pharmaceutical research for its ability to induce diabetes and destroy beta cells. This property makes it valuable in studying the effects of diabetes and developing potential treatments.
Used in Chemical Synthesis:
In the chemical industry, Alloxan Monohydrate is used as a precursor to prepare purple dye murexide, which has various applications in the dye and pigment sector.
Used in Oxidation Reactions:
Due to its strong oxidizing properties, Alloxan Monohydrate is utilized in various oxidation reactions in chemical processes, contributing to the synthesis of different compounds and materials.

Safety Profile

Poison by intravenous route. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Recrystallisation from H2O gave the tetrahydrate in large prisms or rhombs. On heating at 100o, or on exposure to air, this is converted to the monohydrate. Dissolve it in its own weight of boiling H2O and cool it for several days below 0o; the tetrahydrate crystallises from solution much more slowly when free from HNO3. It is less soluble in bicarbonate solutions than in H2O. Drying the solid over H2SO4 yields the monohydrate. The anhydrous crystals can be obtained by recrystallisation from dry Me2CO or AcOH followed by washing with dry Et2O, or by sublimation in a vacuum. On heating it turns pink at 230o and decomposes at ca 256o. It is acidic to litmus. [Hartman & Sheppard Org Synth Coll Vol III 37 1955.] It forms a compound with urea which crystallises from H2O in yellow needles that become red at 170o and decompose at 185-186o. [Beilstein 24 H 500, 24 I 428, 24 II 301, 24 III/IV 2137.]

InChI:InChI=1/C4H2N2O4.H2O/c7-1-2(8)5-4(10)6-3(1)9;/h(H2,5,6,8,9,10);1H2

Synthetic route

N-(2-Ethyl-phenyl)-benzene-1,2-diamine (116138-07-9) + alloxan monohydrate (2244-11-3) → 10-(2-Ethyl-phenyl)-10H-benzo[g]pteridine-2,4-dione (116138-09-1)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 0.5h;	83.3%

1-(4'-methoxy-biphenyl-4-yl)-ethanone (13021-18-6) + alloxan monohydrate (2244-11-3) → C19H16N2O6 (1416355-06-0)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	82%

alloxan monohydrate (2244-11-3) + 4-acetyl-4'-(methylthio)<1,1'-biphenyl> (83085-94-3) → C19H16N2O5S (1416355-08-2)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	80%

N-(4-acetylphenyl)-4-methoxybenzenesulfonamide + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)-4-methoxybenzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	76%

C14H12N2O5S + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)-3-nitrobenzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	74%

C15H12F3NO3S (1088162-86-0) + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)-4-(trifluoromethyl) benzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	73%

N-(4-acetylphenyl)-4-fluorobenzenesulfonamide (347320-93-8) + alloxan monohydrate (2244-11-3) → 4-fluoro-N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5 yl)acetyl)phenyl)benzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	72%

4-(p-toluenesulfonylamino)acetophenone (5317-94-2) + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)-4-methyl benzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	71%

4-acetyl-4'-methylbiphenyl (5748-38-9) + alloxan monohydrate (2244-11-3) → C19H16N2O5 (1416355-03-7)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	69%

1-[4-(trifluoromethoxy)[1,1'-biphenyl]-4-yl-]-1-ethanone (282095-74-3) + alloxan monohydrate (2244-11-3) → C19H13F3N2O6 (1416355-07-1)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	69%

N-(4-acetylphenyl)-3-methylbenzenesulfonamide + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-Hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)-3-methylbenzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	68%

N-(4-acetylphenyl)benzenesulfonamide (76883-69-7) + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)benzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	67%

N-(4-acetylphenyl)-4-nitrobenzenesulfonamide (5433-86-3) + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)-4-nitrobenzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	67%

4-Acetyl-4'-methylsulfonyl-biphenyl (16734-96-6) + alloxan monohydrate (2244-11-3) → C19H16N2O7S (1416355-09-3)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	65%

1-(3'-nitrobiphenyl-4-yl)ethanone (5002-11-9) + alloxan monohydrate (2244-11-3) → C18H13N3O7 (1416355-02-6)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	64%

N-(4-acetylphenyl)-3-fluorobenzenesulfonamide (690961-82-1) + alloxan monohydrate (2244-11-3) → 3-fluoro-N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)benzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	63%

methyl 2-((2-aminophenyl)amino)benzoate (5814-40-4) + alloxan monohydrate (2244-11-3) → 2-(2,4-Dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-benzoic acid methyl ester (116138-10-4)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 0.5h;	62.5%

alloxan monohydrate (2244-11-3) + 4-(N,N-dimethylaminocarbonyl)phenylboronic acid (405520-68-5) → C21H19N3O6 (1416355-12-8)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	62%

alloxan monohydrate (2244-11-3) + 1-(4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)ethan-1-one → C19H16N2O6 (1416355-05-9)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	62%

C15H12F3NO3S + alloxan monohydrate (2244-11-3) → N-(4-(2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)acetyl)phenyl)-2-(trifluoromethyl) benzenesulfonamide

Conditions	Yield
With acetic acid at 115℃; for 3h;	62%

4'-(4-chlorophenyl)acetophenone (5002-07-3) + alloxan monohydrate (2244-11-3) → C18H13ClN2O5 (1416355-04-8)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	60%

alloxan monohydrate (2244-11-3) + 2-amino-benzenethiol (137-07-5) → spiro (106609-62-5)

Conditions	Yield
In acetonitrile for 5h; Heating;	57%

4,4'-diacetylbiphenyl (787-69-9) + alloxan monohydrate (2244-11-3) → C20H16N2O6 (1416355-10-6)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	55%

N1-(biphenyl-2-yl) benzene-1,2-diamine (101908-73-0) + alloxan monohydrate (2244-11-3) → 10-Biphenyl-2-yl-10H-benzo[g]pteridine-2,4-dione (116138-08-0)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 0.5h;	54.5%

3-(methylamino)-4-aminoacetophenone (92642-29-0) + alloxan monohydrate (2244-11-3) → 8-acetyl-10-methylisoalloxazine (79127-38-1)

Conditions	Yield
In hydrogenchloride; ethanol for 0.333333h; Heating;	51%

alloxan monohydrate (2244-11-3) + 1-(4-(thiophen-3-yl)phenyl)ethan-1-one (172035-84-6) → C16H12N2O5S (1416355-13-9)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	49%

1-(4-biphenylyl)-2-propanone (5333-01-7) + alloxan monohydrate (2244-11-3) → C19H16N2O5 (1416355-14-0) + C19H16N2O5 (1416355-15-1)

Conditions	Yield
With acetic acid at 115℃; for 3h; Reflux;	A 27% B 48%

N-1-dodecyl ortho-phenylenediamine (64241-76-5) + alloxan monohydrate (2244-11-3) → 10-dodecyl-10H-benzo[g]pteridine-2,4-dione (79828-16-3)

Conditions	Yield
With boric acid In methanol at 60℃; for 1h; Yield given;

N-(2-Benzhydrylsulfanyl-ethyl)-benzene-1,2-diamine (1035802-16-4) + alloxan monohydrate (2244-11-3) → 10-(2-diphenylmethylthio)ethylisoalloxazine (116385-06-9)

Conditions	Yield
With hydrogenchloride; ethanol 110-115 degC, 30 min. then r.t., 24 h; Yield given;

alloxan monohydrate (2244-11-3) + 1-(2-Amino-3-methylamino-phenyl)-ethanone → 6-acetyl-10-methylisoalloxazine (92642-15-4)

Conditions	Yield
In hydrogenchloride; ethanol 1.) 50-60 deg C, 70 min; 2.) reflux, 15 min;	498 mg

Downstream Products

• 116138-10-4 2-(2,4-Dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-benzoic acid methyl ester 
• 79828-16-3 10-dodecylisoalloxazine 
• 116138-08-0 10-Biphenyl-2-yl-10H-benzo[g]pteridine-2,4-dione 
• 116138-09-1 10-(2-Ethyl-phenyl)-10H-benzo[g]pteridine-2,4-dione 
• 116385-06-9 10-(2-diphenylmethylthio)ethylisoalloxazine 
• 76002-68-1 2-amino-6,7-dichloroquinoxaline 
• 82060-77-3 5-Hydroxy-5-(1-phenyl-2-pyrrolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione 
• 1338684-74-4 tert-butyl (1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-3-phenylpropan-2-yl)carbamate 
• 1416355-12-8 C₂₁H₁₉N₃O₆ 
• 1416355-02-6 C₁₈H₁₃N₃O₇ 
• 1416355-03-7 C₁₉H₁₆N₂O₅ 
• 1416355-04-8 C₁₈H₁₃ClN₂O₅ 
• 1416355-05-9 C₁₉H₁₆N₂O₆ 
• 1416355-06-0 C₁₉H₁₆N₂O₆ 

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