5157-15-3

Basic information

• Product Name: 3a,6a-Diphenyloctahydroimidazo[4,5-d]imidazole-2,5-dione
• Synonyms: 3a,4,6,6a-Tetrahydro-3a,6a-diphenylimidazo[4,5-d]imidazole-2,5(1H,3H)-dione;3a,6a-Diphenyl-3a,4,6,6a-tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione;3a,6a-Diphenylglycoluril;3a,6a-Diphenyloctahydroimidazo[4,5-d]imidazole-2,5-dione;Diphenylglycoluril;3a,6a-Diphenylglycouril;3a,6a-Diphenylperhydroimidazo[4,5-d]imidazole-2,5-dione;3a,6a-DiphenyloctahydroiMidazo[4,5-d]iMidazole-2,5
• CAS NO: 5157-15-3
• Molecular Formula: C₁₆H₁₄N₄O₂
• Molecular Weight: 294.31
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5157-15-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 677.1 °C at 760mmHg
• Flash Point: 277.6 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 3.45E-18mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Ethanol (Slightly)
• PKA: 11?+-.0.60(Predicted)
• CAS DataBase Reference: 3a,6a-Diphenyloctahydroimidazo[4,5-d]imidazole-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3a,6a-Diphenyloctahydroimidazo[4,5-d]imidazole-2,5-dione(5157-15-3)
• EPA Substance Registry System: 3a,6a-Diphenyloctahydroimidazo[4,5-d]imidazole-2,5-dione(5157-15-3)

Safety Data

• Hazardous Substances Data: 5157-15-3(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

Different sources of media describe the Uses of 5157-15-3 differently. You can refer to the following data:
1. A bicyclic bis-urea derivative. Studies suggest that it has potential anticonvulsant activity. An impurity found in the synthesis of Phenytoin (D491650).
2. Diphenylglycoluril is a bicyclic bis-urea derivative. Studies suggest that it has potential anticonvulsant activity.Diphenylglycoluril is also an impurity found in the synthesis of Phenytoin (D491650).

InChI:InChI=1/C16H14N4O2/c21-13-17-15(11-7-3-1-4-8-11)16(19-13,20-14(22)18-15)12-9-5-2-6-10-12/h1-10H,(H2,17,19,21)(H2,18,20,22)

Upstream product

• 64-18-6 formic acid 
• 57-13-6 urea 
• 71-43-2 benzene 
• 134-81-6 benzil 
• 807334-29-8 urea phosphate 
• 123351-47-3 3a,7a-diphenyltetrahydroimidazo<4,5-d>imidazole-2,5-dithione 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 23865-30-7 1,1'-phenylmethanediyl-bis-urea 
• 598-94-7 1,1-Dimethylurea 

Downstream Products

• 1584121-32-3 1,3,4,6-Tetrabromo-3α,6α-diphenylglycoluril 
• 51592-06-4 1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril 
• 106319-03-3 5,7,12,13b,13c,14-Hexahydro-1,4,8,11-tetramethoxy-13b,13c-diphenyl-6H,13H-5a,6a,12a,13a-tetraazabenz<5,6>azuleno<2,1,8-ija>benzazulene-6,13-dione 
• 154230-91-8 1,3,4,6-Tetrakis(acetoxymethyl)tetrahydro-3a,6a-diphenylimidazo<4,5-d>imidazole-2,5(1H,3H)-dione 
• 133729-62-1 5,7,12,13b,13c,14-hexahydro-1,4-dimethoxy-13b,13c-diphenyl-6H,13H-5a,6a,12a,13a-tetraazabenz<5,6>azuleno<2,1,8-ija>benzazulene-6,13-dione 
• 146443-42-7 1,3,4,6-Tetrakis(chloromethyl)tetrahydro-3a,6a-diphenylimidazo<4,5-d>imidazole-2,5(1H,3H)-dione 
• 106319-01-1 5,7,12,13b,13c,14-Hexahydro-13b,13c-diphenyl-6H,13H-5a,6a,12a,13a-tetraazabenz<5,6>azuleno<2,1,8-ija>benzazulene-6,13-dione 
• 106319-02-2 5,7,12,13b,13c,14-hexahydro-1,4,8,11-tetrahydroxy-13b,13c-diphenyl-6H,13H-5a,6a,12a,13a-tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13-dione 
• 125232-27-1 1,3,4,6-tetrakis<6-<4-(hydroxymethyl)-2-methoxyphenoxy>hexyl>tetrahydro-3a,6a-diphenylimidazo<4,5-d>imidazole-2,5(1H,3H)-dione 
• 740800-73-1 (3-carboxymethyl-1,4-dioxo-2a,10b-diphenyl-2a,3,4,5,10,10b-hexahydro-2,3,4a,10a-tetraaza-benzo[g]cyclopenta[cd]azulen-2-yl)-acetic acid 
• 740800-74-2 (3-chlorocarbonylmethyl-1,4-dioxo-2a,10b-diphenyl-2a,3,4,5,10,10b-hexahydro-2,3,4a,10a-tetraaza-benzo[g]cyclopenta[cd]azulen-2-yl)-acetyl chloride 
• 740800-72-0 (3-methoxycarbonylmethyl-1,4-dioxo-2a,10b-diphenyl-2a,3,4,5,10,10b-hexahydro-2,3,4a,10a-tetraaza-benzo[g]cyclopenta[cd]azulen-2-yl)-acetic acid methyl ester 
• 740800-71-9 2a,10b-diphenyl-2a,5,10,10b-tetrahydro-2H,3H-2,3,4a,10a-tetraaza-benzo[g]cyclopenta[cd]azulene-1,4-dione 
• 125232-26-0 1,3,4,6-tetrakis<6-(4-formyl-2-methoxyphenoxy)hexyl>tetrahydro-3a,6a-diphenylimidazo<4,5-d>imidazole-2,5(1H,3H)-dione 

Relevant articles and documents

One step liquid phase heterogeneous synthesis of phenytoin over MgAl calcined hydrotalcites

Heterogeneous liquid phase synthesis of phenytoin (5,5-diphenylhydantoin) was carried out over MgAl calcined hydrotalcites for the first time under environmental friendly conditions. The catalytic activity results showed very high conversion (80-95%) and selectivity (90-95%) of the desired product phenytoin over MgAl calcined hydrotalcites. The calcined hydrotalcites can be recycled without further loss in the activity and the possible mechanism of the reaction is also proposed.

Synthesis of Glycoluril using Urea Phosphate

Abstract: Glycolurils are building blocks for the synthesis of cucurbiturils that are important host materials for several applications. Glycolurils are prepared conveniently by the condensation of 1,2-diketones with urea using an acid as catalyst. Herein, we report a facile method of synthesis of various glycolurils using urea phosphate and 1,2-diketones.

Oxidation of Thioamides to Amides with Tetrachloro- and Tetrabromoglycolurils

Tetrabromo- and tetrachloroglycolurils have been shown to act as good oxidants capable of converting thioamides to the corresponding amides. This approach offers such advantages as good yields (81–99%), short reaction times (10–25 min), simple workup procedure, and environmental safety.

Synthesis of glycoluril catalyzed by potassium hydroxide under ultrasound irradiation

Synthesis of the glycolurils catalyzed by potassium hydroxide was carried out in 17-75% yield at 40 °C in EtOH under ultrasound irradiation. Compared to the method using stirring, the main advantage of the present procedure is milder conditions and shorter reaction time.