Glycoluril

Base Information

• Chemical Name: Glycoluril
• CAS No.: 496-46-8
• Molecular Formula: C4H6N4O2
• Molecular Weight: 142.117
• Hs Code.: 29332990
• European Community (EC) Number: 207-821-5
• NSC Number: 2765
• UNII: U9H2W4OS13
• DSSTox Substance ID: DTXSID6031380
• Nikkaji Number: J1.042.644H,J2.599B
• Wikipedia: Glycoluril
• Wikidata: Q976874,Q27117029
• Metabolomics Workbench ID: 52327
• ChEMBL ID: CHEMBL3182837
• Mol file: 496-46-8.mol

Synonyms:acetylene carbamide;acetylenediureine;acetyleneurea;glycoluril;glyoxaldiureine;perhydroimidazo(4,5-d)imidazole-2,5-dione;tetrahydroimidazo(4,5-d)imidazole-2,5(1H,3H)-dione

Chemical Property of Glycoluril

Chemical Property:

• Appearance/Colour: white to very slightly yellow crystalline powder
• Vapor Pressure: 4.61E-30mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.514
• Boiling Point: 861.601 °C at 760 mmHg
• PKA: 12.91±0.20(Predicted)
• Flash Point: 421.795 °C
• PSA: 82.26000
• Density: 1.42 g/cm³
• LogP: -0.42060
• Storage Temp.: Store below +30°C.
• Solubility.: 15g/l
• Water Solubility.: 1.8g/L at 20℃
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.04907545
• Heavy Atom Count: 10
• Complexity: 165

Purity/Quality:

99.9% ^*data from raw suppliers

Glycouril ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C12C(NC(=O)N1)NC(=O)N2
• Uses: Reactant involved in synthesis of:? ;Glycouril hexamers and monofunctionalized cucurbit[6]uril derivatives1,2,3? ;N-chloro compounds from trichloroisocyanuric acid4? ;Glycouril trimers5 For derivatives glycoluril, glycoluril resins Glycoluril is used as a reagent in the synthesis of acyclic cucurbit[n]uril molecular containers which can enhance the solubility and bioactivity of poorly soluble pharmaceuticals. Also used as a reagent in the synthesis of cucurbit[7]uril containers for targeted delivery of oxaliplatin to cancer cells.

Technology Process of Glycoluril

There total 16 articles about Glycoluril which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

Glyoxal (131543-46-9,107-22-2) + urea (57-13-6) → 4,5-dihydroxy-2-imidazolidinone (3720-97-6) + glycoluril (496-46-8)

Guidance literature:

With sodium hydrogencarbonate; In water; at 40 - 60 ℃; for 6h; under 760.051 Torr; pH=5.5 - 6.1; Reagent/catalyst; Sealed tube;

Reference yield: 96.0%

dithioglycoluril → glycoluril (496-46-8)

Guidance literature:

With tetrabromoglycoluril; In ethanol; at 40 ℃; for 0.25h; Reagent/catalyst; Green chemistry;

DOI:10.1134/S1070428019120108

Reference yield: 92.0%

Glyoxal (131543-46-9,107-22-2) + urea (57-13-6) → glycoluril (496-46-8)

Guidance literature:

With sulfuric acid; In water; at 90 ℃; for 12h;

DOI:10.1016/j.tetlet.2016.03.013

upstream raw materials:

4,5-dihydroxy-2-imidazolidinone

urea

Glyoxal

trans-4,5-dihydroxy-2-imidazolidinone

Downstream raw materials:

Allantoin

2,6-diacetyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

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

2,4,6,8-tetranitro-2,4,6,8-tetraazabicyclo<3.3.0>octane-3,7-dione

Refernces

• 1、 Sal’keeva,Bakibaev,Khasenova,Taishibekova, Ye. K.,Sugralina,Minaeva, Ye. V.,Sal’keeva. "Effect of glycoluril and its derivatives on the flame resistance and physico-mechanical properties of rubber". . p. 132 - 139. Retrieved 2016.
• 2、 Havel, Vaclav,Babiak, Michal,Sindelar, Vladimir. "Modulation of Bambusuril Anion Affinity in Water". . p. 8963 - 8968. Retrieved 2017.
• 3、 -. "D - galactose bonded ring-opening cucurbituril and application thereof". Paragraph 0032. . Retrieved 2021/06/22.
• 4、 Karpagalakshmi, K.,Lakshminarayanan, P.,Prakash, R.,Ramalakshmi, S.,Selvapalam, N.,Usha, G.,Yang, C.. "Synthesis of Glycoluril using Urea Phosphate". . p. 1988 - 1992. Retrieved 2022/01/24.