Tetramethylol acetylenediurea supplier

Name
Tetramethylol acetylenediurea
EINECS 226-408-0
CAS No. 5395-50-6
Article Data8
CAS DataBase
Density 1.697 g/cm³
Solubility
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
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 128.02000
LogP -3.33540

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

Conditions	Yield
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

Conditions	Yield
Alkaline conditions;

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: L-methionine potassium salt

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: (S,S)-2-[6-(1-carboxy-2-methylthiopropyl)-4,8-dioxotetrahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluoren-2-yl]-4-methylthiobutanoic acid

Conditions

Conditions	Yield
In water at 90℃; for 2h;	65%

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 2,6-di(bromomethyl)-4,8-dihydroxymethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions

Conditions	Yield
With phosphorus tribromide In toluene at 60 - 90℃; for 24h;	62.5%

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 2,6-di(chloromethyl)-4,8-dihydroxymethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions

Conditions	Yield
With phosphorus trichloride In acetonitrile at 0 - 80℃; for 24h;	60.96%

: 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

: 1586777-54-9
2,4,6,8-tetramethylamino-{2-(4-phenylthiazolyl)-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione}

Conditions

Conditions	Yield
In methanol; water	58%

: 22504-72-9
N,N'-dimethylsulfamide

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 263411-62-7
3,5,11,13-tetramethyl-8,16-dioxo-4,12-dithia-1,3,5,7,9,11,13,15-octaazatetracyclo[7.7.2.07,17.015,18]octadecane 4,4,12,12-tetraoxide

Conditions

Conditions	Yield
With hydrogenchloride at 80 - 90℃; for 2h; pH=1;	55%

: C5H10NO2(1-)*K(1+)

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: (S,S)-2-[6-(1-carboxybutyl)-4,8-dioxotetrahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluoren-2-yl]pentanoic acid

Conditions

Conditions	Yield
In water at 90℃; for 2h;	46%

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: potassium salt of valine

: (S,S)-2-[6-(1-carboxy-2-methylpropyl)-4,8-dioxotetrahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluoren-2-yl]-3-methylbutanoic acid

Conditions

Conditions	Yield
In water at 90℃; for 2h;	45%

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 123-30-8
4-amino-phenol

: 4,4'-(methanediyldiamino)diphenol

Conditions

Conditions	Yield
In neat (no solvent) at 140 - 150℃; for 0.5h;	44%

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 920-46-7
Methacryloyl chloride

: 1,3,4,6-tetrakis(methacryloyloxymethyl)glycoluril

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; Cooling with ice;	27%

: 598-94-7
1,1-Dimethylurea

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 3,9-bis(N,N-dimethylcarbamoyl)-1,3,5,7,9,11-hexaazatetracyclo[9.2.1.0(5,13).0(7,12)]tetradecane-6,14-dione

Conditions

Conditions	Yield
With hydrogenchloride In water at 60 - 65℃; for 5h; pH=1;	15%

: 96-31-1
N,N'-Dimethylurea

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 3,5,11,13-tetramethyl-1,3,5,7,9,11,13,15-octaazatetra-cyclo[13.2.1.0(7,17).0(9,16)]octadecane-4,8,12,18-tetraone

Conditions

Conditions	Yield
With hydrogenchloride In water at 60 - 65℃; for 7h; pH=1;	15%

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 71-36-3
butan-1-ol

: 1,3,4,6-tetrakis(butoxymethyl)glycoluril

Conditions

Conditions	Yield
With nitric acid In dimethyl sulfoxide at 60℃; for 16h;	11%

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 75-64-9
tert-butylamine

: 2,6-di(tert-butyl)hexahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione

Conditions

Conditions	Yield
In water at 40℃; for 16h;	36.1 g

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 813-77-4
Dimethyl chlorophosphate

A: C10H16N4O6P2

B: C12H24N4O10P2

Conditions

Conditions	Yield
With pyridine In benzene at 0 - 70℃; for 24h; Green chemistry; Overall yield = 50.25 %; Overall yield = 2 g;

...Expand

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 111-27-3
hexan-1-ol

: C32H62N4O6

Conditions

Conditions	Yield
With nitric acid In dimethyl sulfoxide at 60℃; for 16h;	0.15 g

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: 108-93-0
cyclohexanol

: 1,3,4,6-tetrakis(cyclohexoxymethyl)glycoluril

Conditions

Conditions	Yield
With nitric acid Heating;

: 2081-44-9
Tetrahydro-pyran-4-ol

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: C28H46N4O10

Conditions

Conditions	Yield
With nitric acid at 60℃; for 16h;

: 4534-74-1
4-ethylcyclohexanol

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: C40H70N4O6

Conditions

Conditions	Yield
With nitric acid In dimethyl sulfoxide at 60℃; for 16h;

: 589-91-3
p-methylcyclohexanol

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

: C36H62N4O6

Conditions

Conditions	Yield
With nitric acid In dimethyl sulfoxide at 60℃; for 16h;

: 5395-50-6
1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

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

B: 2,4-dimethylol-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

C: 2,6-dimethylol-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

D: 2,8-dimethylol-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions

Conditions	Yield
With water at 100℃; for 0.333333h; Temperature;

...Expand

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

Product Name

Tetramethylol acetylenediurea

Synthetic route

Tetramethylol acetylenediurea Specification

Related Products

Hot Products