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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
MKCM5831
MKCK3169
MKCC6729
MKBS8369V
MKBW9557V

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Zhi-Guo Wang et al.
The Journal of organic chemistry, 71(12), 4502-4508 (2006-06-06)
We report the X-ray crystal structure of 11 molecular clips and analyze the influence of substituents (e.g., OMe, Me, and NO2) and their location on the observed crystal packing. Molecular clips 3a and 3b form tapelike structures in the crystal
Satish S Bhat et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(51), 16383-16392 (2012-10-26)
Complexes of the type [Ru(bxbg)(2) (N-N)](2+), where N-N denotes 2,2'-bipyridine (bpy) (1), 1,10-phenanthroline (phen) (2), dipyrido[3,2-d:2',3-f] quinoxaline (dpq) (3), and dipyrido[3,2-a:2',3'-c]phenazine (dppz) (4), incorporating bis(o-xylene)bipyridine-glycoluril (bxbg) as an ancillary "molecular clip" ligand, have been synthesized and characterized. These ruthenium(II) complexes
Dariush Ajami et al.
Nature chemistry, 1(1), 87-90 (2009-04-01)
Simple alkanes feature fully extended conformations as their lowest-energy shapes but can assume coiled, compressed conformations in small spaces. A series of normal alkanes, C(16) to C(19), were encapsulated in self-assembled, hydrogen-bonded complexes. Coiling of the longer alkanes was observed
Encapsulated carboxylic acid dimers with compressed hydrogen bonds.
Dariush Ajami et al.
Angewandte Chemie (International ed. in English), 50(2), 528-531 (2010-12-15)
Darren W Johnson et al.
Chemical communications (Cambridge, England), (19)(19), 2228-2229 (2002-10-26)
A series of substituted glycoluril molecules exhibits a substantial twist of the fused five-membered rings and assembles exclusively chiral hydrogen-bonded ribbons in the solid-state.
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