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G7305

Sigma-Aldrich

Glycoluril

97%

Synonym(s):

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

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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

Quality Level

100

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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW6227
MKCT6877
MKCM5831
MKCK3169
MKCC6729

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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
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
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
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+)).
Arindam Chakraborty et al.
Journal of the American Chemical Society, 124(28), 8297-8306 (2002-07-11)
Cucurbit[6]uril (CB[6]) is a macrocyclic compound, prepared in one pot from glycoluril and formaldehyde, whose molecular recognition properties have made it the object of intense study. Studies of the mechanism of CB[n] formation, which might provide insights that allow the
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