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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

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

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’.

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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
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
Y K Stella Man et al.
Scientific reports, 9(1), 12840-12840 (2019-09-08)
Early phase clinical trials have demonstrated good therapeutic index for oncolytic adenoviruses in patients with solid tumours when administered intratumorally, resulting in local tumour elimination. Entrapment and binding of adenovirus to erythrocytes, blood factors, and neutralising antibodies have prevented efficient
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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