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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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5 G
$42.75
100 G
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About This Item

Empirical Formula (Hill Notation):
C4H6N4O2
CAS Number:
496-46-8
Molecular Weight:
142.12
Beilstein/REAXYS Number:
128826
EC Number:
207-821-5
MDL number:
MFCD00005539
UNSPSC Code:
12352100
PubChem Substance ID:
24895300
NACRES:
NA.22

$42.75

List Price$45.00Save 5%
Web-Only Promotion

Available to ship onMay 01, 2025Details

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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

11 - Combustible Solids

wgk_germany

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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Derick Lucas et al.
Organic letters, 13(15), 4112-4115 (2011-07-12)
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
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+)).
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
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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