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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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Anxin Wu et al.
The Journal of organic chemistry, 67(16), 5817-5830 (2002-08-03)
Methylene-bridged glycoluril dimers are the fundamental building blocks of cucurbituril (CB[6]), its homologues (CB[n]), and its derivatives. This paper describes three complementary methods for the synthesis of C- and S-shaped methylene-bridged glycoluril dimers (29-34 and 37-44). For this purpose, we
Konrad Tiefenbacher et al.
Chemical communications (Cambridge, England), 47(26), 7341-7343 (2011-06-02)
The synthesis of an azo-benzene glycoluril supergelator is reported. The control over the gel/sol state can be accomplished by irradiation and heat, but also (in a unidirectional sense) by incorporation of the glycoluril into a more stable supramolecular assembly.
Chandra Kanth P et al.
ACS omega, 6(4), 3024-3036 (2021-02-09)
A supramolecular cucurbit[6]uril (CB[6])-enriched magnetic montmorillonite (CBCM) nanocomposite was prepared and characterized. CB[6] played a prominent role as a capping agent, helping in better distribution of the nanoparticles, and as a binder between nanoparticles. Montmorillonite provided structural stability and fortified
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
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