Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

View All Documentation

G7305

Sigma-Aldrich

Glycoluril

97%

Synonym(s):

Acetylene carbamide, Acetylenediurea, NSC 2765, Tetrahydroimidazo[4,5-d]imidazole-2,5-dione

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C4H6N4O2
CAS Number:
496-46-8
Molecular Weight:
142.12
Beilstein:
128826
EC Number:
207-821-5
MDL number:
MFCD00005539
UNSPSC Code:
12352100
PubChem Substance ID:
24895300
NACRES:
NA.22

Assay

97%

mp

>300 °C (lit.)

SMILES string

O=C1NC2NC(=O)NC2N1

InChI

1S/C4H6N4O2/c9-3-5-1-2(7-3)8-4(10)6-1/h1-2H,(H2,5,7,9)(H2,6,8,10)

InChI key

VPVSTMAPERLKKM-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

Reactant involved in synthesis of:
  • Glycouril hexamers and monofunctionalized cucurbit[6]uril derivatives
  • N-chloro compounds from trichloroisocyanuric acid
  • Glycouril trimers

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Dariush Ajami et al.
Journal of the American Chemical Society, 128(47), 15038-15039 (2006-11-23)
A cylindrical capsule containing a coiled alkane incorporates spacers. The alkane lengthens and gauche strain is relieved. The spacer can be removed to reset the system to the original state. The system represents a spring-loaded device that operates reversibly in
Megha S Deshpande et al.
Bioconjugate chemistry, 20(3), 447-459 (2009-02-25)
Nine complexes of the type [Ru(N-N)(2)(BPG)]Cl(2) 1-4, [Ru(N-N)(BPG)(2)]Cl(2) 5-8, and [Ru(BPG)(3)]Cl(2) 9 where N-N is 2,2'-bipyridine (bpy), 1,10-phenanthroline (phen), dipyrido[3,2-d:2',3'-f]quinoxaline (dpq), dipyrido[3,2-a:2',3'-c]phenazine (dppz), which incorporates bipyridine-glycoluril (BPG-4b,5,7,7a-tetrahydro-4b,7a-epiminomethanoimino-6H-imidazo[4,5-f][1,10]phenanthroline-6,13-dione) as the ancillary ligand, have been synthesized and characterized. These complexes with the
Wolfgang-Andreas C Bauer et al.
Advanced materials (Deerfield Beach, Fla.), 23(45), 5404-5408 (2011-10-20)
Electron beam lithography is a powerful technique for the production of nanostructures but pattern quality depends on numerous interacting process variables. Orthogonal gradients of resist composition, baking temperatures, and development time as well as dose variations inside writing fields are
Derick Lucas et al.
Organic letters, 13(15), 4112-4115 (2011-07-12)
The fragmentation reaction of bis-nor-seco-CB[10] with 3,5-dimethylphenol (3) delivers methylene bridged glycoluril pentamer 5 in 81% yield. The host-guest recognition properties of the previously known tetramer 4 and those of pentamer 5 and hexamer 6 toward cationic guests in water
Wei-Hao Huang et al.
Organic letters, 11(17), 3918-3921 (2009-08-07)
In a process reminiscent of RNA folding, acyclic glycoluril decamer (+/-)-1 undergoes double helical assembly (red/green strands) in water triggered by the neutralization of regions of high electrostatic surface potential by metal cations (Li(+), Na(+), K(+), Ca(2+)).
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service