G7305
Glycoluril
97%
Synonym(s):
Acetylene carbamide, Acetylenediurea, NSC 2765, Tetrahydroimidazo[4,5-d]imidazole-2,5-dione
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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C4H6N4O2
CAS Number:
Molecular Weight:
142.12
Beilstein:
128826
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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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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+)).
Derick Lucas et al.
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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
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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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