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Glycoluril

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Name

Glycoluril

EINECS 207-821-5
CAS No. 496-46-8 Density 1.42 g/cm3
PSA 82.26000 LogP -0.42060
Solubility 1.8g/L at 20℃ Melting Point >300 °C(lit.)
Formula C4H6N4O2 Boiling Point 861.601 °C at 760 mmHg
Molecular Weight 142.117 Flash Point 421.795 °C
Transport Information N/A Appearance white to very slightly yellow crystalline powder
Safety 24/25 Risk Codes 22
Molecular Structure Molecular Structure of 496-46-8 (Glycoluril) Hazard Symbols Xn
Synonyms

Glycoluril(6CI,7CI,8CI);Acetylene carbamide;Acetylenediurea;Acetylenediureine;Acetyleneurea;Diurea glyoxalate;Glyoxalbiuret;Glyoxaldiureine;Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione,tetrahydro-;Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione;Tetrahydroimidazo[4,5-d]imidazole-2,5-dione;

Article Data 37

Glycoluril Synthetic route

A

3720-97-6

4,5-dihydroxy-2-imidazolidinone

B

496-46-8

glycoluril

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 40 - 60℃; under 760.051 Torr; for 6h; pH=5.5 - 6.1; Reagent/catalyst; Sealed tube;A 99.3%
B n/a

dithioglycoluril

496-46-8

glycoluril

Conditions
ConditionsYield
With tetrabromoglycoluril In ethanol at 40℃; for 0.25h; Reagent/catalyst; Green chemistry;96%
496-46-8

glycoluril

Conditions
ConditionsYield
With sulfuric acid In water at 90℃; for 12h;92%
With sulfuric acid In water at 70 - 80℃; for 1h;88%
With sulfuric acid In water at 75℃; for 1h;88%
3720-97-6

4,5-dihydroxy-2-imidazolidinone

6630-04-2

1,3-bis(5-carboxypentyl)urea

A

496-46-8

glycoluril

B

2,4-bis(5-carboxypentyl)glycoluril

Conditions
ConditionsYield
With hydrogenchloride In water for 3h; Reflux;A n/a
B 80%
97-59-6

Allantoin

496-46-8

glycoluril

Conditions
ConditionsYield
With sodium amalgam; sulfuric acid
599-01-9

3,3,3-trichloro-2-hydroxy-propionic acid

496-46-8

glycoluril

Conditions
ConditionsYield
With water
815-53-2

2,3-dioxo-propionic acid

496-46-8

glycoluril

Conditions
ConditionsYield
With hydrogenchloride
acetylenediurein-dicarboxylic acid-(7.8)

acetylenediurein-dicarboxylic acid-(7.8)

496-46-8

glycoluril

Conditions
ConditionsYield
With water
517-21-5

glyoxal sodium bisulfite

A

496-46-8

glycoluril

B

SO2

SO2

Conditions
ConditionsYield
With hydrogenchloride; water ueber den Schmelzpunkt;
496-46-8

glycoluril

108-24-7

acetic anhydride

10543-60-9

2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo<3,3,0>octan-3,7-dione

Conditions
ConditionsYield
With phosphoric acid at 140℃; for 0.5h; Reagent/catalyst;98%
With sodium acetate at 140℃; for 4h;88%
With sodium acetate for 4h; Heating;88%
With perchloric acid In water at 20℃; Cooling with ice;80%
Acidic conditions;

Glycoluril Chemical Properties


IUPAC Name: 1,3,3a,4,6,6a-Hexahydroimidazo[4,5-d]imidazole-2,5-dione
Molecular Formula: C4H6N4O2
Molecular Weight: 142.12 g/mol
SMILES: C12C(NC(N1)=O)NC(N2)=O
InChI: InChI=1/C4H6N4O2/c9-3-5-1-2(7-3)8-4(10)6-1/h1-2H,(H2,5,7,9)(H2,6,8,10)
EINECS: 207-821-5
Product Categories: Heterocyclic Compounds
Melting Point: >300 °C(lit.)
Index of Refraction: 1.514 
Molar Refractivity: 30.15 cm
Molar Volume: 100 cm3 
Polarizability: 11.95×10-24 cm3 
Surface Tension: 39.1 dyne/cm 
Density: 1.42 g/cm3 
Flash Point: 421.8 °C 
Enthalpy of Vaporization: 125.21 kJ/mol 
Boiling Point: 861.6 °C at 760 mmHg 
Vapour Pressure of Glycoluril (CAS NO.496-46-8): 4.61E-30 mmHg at 25 °C

Glycoluril Safety Profile

Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany of Glycoluril (CAS NO.496-46-8): 1

Glycoluril Specification

 Glycoluril (CAS NO.496-46-8), its Synonyms are Acetylene carbamide ; Acetylenediurea ; Acetylenediureine ; Diurea glyoxalate ; Glyoxalbiuret ; Glyoxaldiureine ; Glyoxaldiurene ; Tetrahydroimidaz(d)imidazole-2,5(1H,3H)-dione ; Glycoluril (8CI) ; Imidazo(4,5-d)imidazole-2,5(1H,3H)-dione, tetrahydro- ; Perhydroimidazo(4,5-d)imidazole-2,5-dione . It is white to very slightly yellow crystalline powder.

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