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Tetramethylol acetylenediurea
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Name

Tetramethylol acetylenediurea

 EINECS 226-408-0
CAS No. 5395-50-6 Density 1.697 g/cm3
PSA 128.02000 LogP -3.33540
Solubility N/A Melting Point 137-138 °C
Formula C8H14N4O6 Boiling Point 624.2 °C at 760 mmHg
Molecular Weight 262.222 Flash Point 331.3 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 5395-50-6 (Tetramethylol acetylenediurea) Hazard Symbols N/A
Synonyms

Glycoluril,1,3,4,6-tetrakis(hydroxymethyl)- (6CI,7CI,8CI);2,4,6,8-Tetrakis(hydroxymethyl)glycoluril;2,5-Dioxo-1,3,4,6-tetrakis(hydroxymethyl)hexahydroimidazo[4,5-d]imidazole;Cymel 1172;Fixapret 140;N,N',N'',N'''-Tetrakis(hydroxymethyl)glycoluril;NSC3319;NSC 67452;Protectol TD;Tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)imidazol(4,5-d)imidazole-2,5-(1H,3H)dione;Tetrakis(hydroxymethyl)acetylenediurea;Tetrakis(hydroxymethyl)acetyleneurea;Tetrakis(hydroxymethyl)glycoluril;Tetramethylolacetylenediurea;Tetramethylolglycoluril;

Article Data 8

Tetramethylol acetylenediurea Synthetic route

50-00-0

formaldehyd

496-46-8

glycoluril

5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Conditions
ConditionsYield
With sodium hydroxide In water at 40 - 55℃; for 0.25h; Reflux;92%
With sodium hydroxide In water at 40 - 55℃; for 0.25h; pH=8 - 8.7;92%
With potassium carbonate In methanol at 50 - 60℃; pH=10 - 12;80%
With sodium hydroxide In water at 50℃; for 2h; pH=9 - 10;50%
With sodium hydroxide In water at 70℃; for 12h; pH=8 - 10;
50-00-0

formaldehyd

496-46-8

glycoluril

A

5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

B

2,4,6-trimethylol-2,4,6,8-tetraazabicyclo[3.3.0]ocatne-3,7-dione

Conditions
ConditionsYield
Alkaline conditions;
5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

94-09-7

p-aminoethylbenzoate

74763-68-1

diethyl 4,4′-(methylenebis(azanediyl))dibenzoate

Conditions
ConditionsYield
In neat (no solvent) at 140 - 150℃; for 0.5h;98%
611-34-7

5-Aminoquinoline

5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

N,N'-di(quinolin-5-yl)methanediamine

Conditions
ConditionsYield
In neat (no solvent) at 140 - 150℃; for 0.5h;97%
5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

100-01-6

4-nitro-aniline

39809-82-0

N,N'-bis-(4-nitrophenyl)methanediamine

Conditions
ConditionsYield
In neat (no solvent) at 140 - 150℃; for 0.5h;95%
13641-96-8

acrylic acid 2-isocyanatoethyl ester

5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

1,3,4,6-tetrakis(2-acryloyloxyethylcarbamoyloxy)methylglycoluril

Conditions
ConditionsYield
With dibutyltin dilaurate In dichloromethane at 20℃; for 24h;95%
5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

62-53-3

aniline

622-14-0

N,N'-diphenylmethylenediamine

Conditions
ConditionsYield
In neat (no solvent) at 140 - 150℃; for 0.5h;94%
5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

59-46-1

Procaine

di(diethylamino)ethyl 4,4'-(methanediyldiamino)dibenzoate

Conditions
ConditionsYield
In neat (no solvent) at 140 - 150℃; for 0.5h;90%
5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

L-tryptophan potassium salt

(S,S)-2-[6-[1-carboxy-2-(1H-indol-2-yl)ethyl]-4,8-dioxotetrahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluoren-2-yl]-3-(1H-indol-2-yl)propanoic acid

Conditions
ConditionsYield
In water at 90℃; for 2h;82%
2010-06-2

2-Amino-4-phenylthiazole

5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

1586777-53-8

3,9-bis[2-(4-phenyl)thiazolyl]-1,3,5,7,9,11-hexaazatetracyclo[5.5.2.03,14.09,13]tetradodeca-6,12-dione

Conditions
ConditionsYield
In methanol; water for 4h;68%

Tetramethylol acetylenediurea Specification

The Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione,tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)-, with the CAS registry number 5395-50-6, is also known as Tetramethylolglycoluril. Its EINECS registry number is 226-408-0. This chemical's molecular formula is C8H14N4O6 and molecular weight is 262.21996. What's more, its IUPAC name is 1,3,4,6-Tetrakis(hydroxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione.

Physical properties about Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione,tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)- are: (1)ACD/LogP: -0.90; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.9; (4)ACD/LogD (pH 7.4): -0.9; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 7.73; (8)ACD/KOC (pH 7.4): 7.73; (9)#H bond acceptors: 10; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 84.02 Å2; (13)Index of Refraction: 1.644; (14)Molar Refractivity: 55.94 cm3; (15)Molar Volume: 154.4 cm3; (16)Polarizability: 22.17×10-24cm3; (17)Surface Tension: 86.4 dyne/cm; (18)Density: 1.697 g/cm3; (19)Flash Point: 331.3 °C; (20)Enthalpy of Vaporization: 105.96 kJ/mol; (21)Boiling Point: 624.2 °C at 760 mmHg; (22)Vapour Pressure: 3.38E-18 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1N(C2N(C(=O)N(C2N1CO)CO)CO)CO
(2) InChI: InChI=1/C8H14N4O6/c13-1-9-5-6(11(3-15)7(9)17)12(4-16)8(18)10(5)2-14/h5-6,13-16H,1-4H2
(3) InChIKey: UUGLSEIATNSHRI-UHFFFAOYAY

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