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496-46-8 Usage

Chemical Properties

WHITE TO VERY SLIGHTLY YELLOW CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 496-46-8 differently. You can refer to the following data:
1. Reactant involved in synthesis of:? ;Glycouril hexamers and monofunctionalized cucurbit[6]uril derivatives1,2,3? ;N-chloro compounds from trichloroisocyanuric acid4? ;Glycouril trimers5
2. For derivatives glycoluril, glycoluril resins
3. Glycoluril is used as a reagent in the synthesis of acyclic cucurbit[n]uril molecular containers which can enhance the solubility and bioactivity of poorly soluble pharmaceuticals. Also used as a reagent in the synthesis of cucurbit[7]uril containers for targeted delivery of oxaliplatin to cancer cells.

Flammability and Explosibility

Notclassified

Agricultural Uses

Glycine is the simplest naturally occurring amino acid and is a constituent of most proteins. Its formula is H2N·CH2·COOH.

Check Digit Verification of cas no

The CAS Registry Mumber 496-46-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 6 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 496-46:
(5*4)+(4*9)+(3*6)+(2*4)+(1*6)=88
88 % 10 = 8
So 496-46-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H6N4O2/c9-3-5-1-2(7-3)8-4(10)6-1/h1-2H,(H2,5,7,9)(H2,6,8,10)

496-46-8 Well-known Company Product Price

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  • Detail
  • Aldrich

  • (G7305)  Glycoluril  97%

  • 496-46-8

  • G7305-5G

  • 271.44CNY

  • Detail
  • Aldrich

  • (G7305)  Glycoluril  97%

  • 496-46-8

  • G7305-100G

  • 1,193.40CNY

  • Detail

496-46-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name glycoluril

1.2 Other means of identification

Product number -
Other names Glyoxaldiureine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:496-46-8 SDS

496-46-8Synthetic route

Glyoxal
131543-46-9

Glyoxal

urea
57-13-6

urea

A

4,5-dihydroxy-2-imidazolidinone
3720-97-6

4,5-dihydroxy-2-imidazolidinone

B

glycoluril
496-46-8

glycoluril

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 40 - 60℃; under 760.051 Torr; for 6h; pH=5.5 - 6.1; Reagent/catalyst; Sealed tube;A 99.3%
B n/a
dithioglycoluril

dithioglycoluril

glycoluril
496-46-8

glycoluril

Conditions
ConditionsYield
With tetrabromoglycoluril In ethanol at 40℃; for 0.25h; Reagent/catalyst; Green chemistry;96%
Glyoxal
131543-46-9

Glyoxal

urea
57-13-6

urea

glycoluril
496-46-8

glycoluril

Conditions
ConditionsYield
With sulfuric acid In water at 90℃; for 12h;92%
With sulfuric acid In water at 70 - 80℃; for 1h;88%
With sulfuric acid In water at 75℃; for 1h;88%
4,5-dihydroxy-2-imidazolidinone
3720-97-6

4,5-dihydroxy-2-imidazolidinone

1,3-bis(5-carboxypentyl)urea
6630-04-2

1,3-bis(5-carboxypentyl)urea

A

glycoluril
496-46-8

glycoluril

B

2,4-bis(5-carboxypentyl)glycoluril

2,4-bis(5-carboxypentyl)glycoluril

Conditions
ConditionsYield
With hydrogenchloride In water for 3h; Reflux;A n/a
B 80%
Allantoin
97-59-6

Allantoin

glycoluril
496-46-8

glycoluril

Conditions
ConditionsYield
With sodium amalgam; sulfuric acid
3,3,3-trichloro-2-hydroxy-propionic acid
599-01-9

3,3,3-trichloro-2-hydroxy-propionic acid

urea
57-13-6

urea

glycoluril
496-46-8

glycoluril

Conditions
ConditionsYield
With water
2,3-dioxo-propionic acid
815-53-2

2,3-dioxo-propionic acid

urea
57-13-6

urea

glycoluril
496-46-8

glycoluril

Conditions
ConditionsYield
With hydrogenchloride
acetylenediurein-dicarboxylic acid-(7.8)

acetylenediurein-dicarboxylic acid-(7.8)

glycoluril
496-46-8

glycoluril

Conditions
ConditionsYield
With water
glyoxal sodium bisulfite
517-21-5

glyoxal sodium bisulfite

urea
57-13-6

urea

A

glycoluril
496-46-8

glycoluril

B

SO2

SO2

Conditions
ConditionsYield
With hydrogenchloride; water ueber den Schmelzpunkt;
glycoluril
496-46-8

glycoluril

acetic anhydride
108-24-7

acetic anhydride

2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo<3,3,0>octan-3,7-dione
10543-60-9

2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo<3,3,0>octan-3,7-dione

Conditions
ConditionsYield
With phosphoric acid at 140℃; for 0.5h; Reagent/catalyst;98%
With sodium acetate at 140℃; for 4h;88%
With sodium acetate for 4h; Heating;88%
With perchloric acid In water at 20℃; Cooling with ice;80%
Acidic conditions;
glycoluril
496-46-8

glycoluril

1,3,4,6-tetrachloroglycoluril
776-19-2

1,3,4,6-tetrachloroglycoluril

Conditions
ConditionsYield
With trichloroisocyanuric acid; sodium hydrogencarbonate In water at 20℃; for 3h;97%
glycoluril
496-46-8

glycoluril

parabanic acid
120-89-8

parabanic acid

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water at 75℃; for 2h; Temperature;95%
1,4-butane sultone
1633-83-6

1,4-butane sultone

glycoluril
496-46-8

glycoluril

glycoluril tetrakis(butane-1-sulfonic acid)

glycoluril tetrakis(butane-1-sulfonic acid)

Conditions
ConditionsYield
In acetonitrile for 12h; Reflux;95%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
5395-50-6

1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Conditions
ConditionsYield
With sodium hydroxide In water at 40 - 55℃; for 0.25h; Reflux;92%
With sodium hydroxide In water at 40 - 55℃; for 0.25h; pH=8 - 8.7;92%
With potassium carbonate In methanol at 50 - 60℃; pH=10 - 12;80%
With sodium hydroxide In water at 50℃; for 2h; pH=9 - 10;50%
With sodium hydroxide In water at 70℃; for 12h; pH=8 - 10;
glycoluril
496-46-8

glycoluril

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

1,3,4,6-tetraallyl glycoluril
229162-26-9

1,3,4,6-tetraallyl glycoluril

Conditions
ConditionsYield
Stage #1: glycoluril With sodium hydroxide In dimethyl sulfoxide at 40℃; for 1h;
Stage #2: 3-chloroprop-1-ene In dimethyl sulfoxide at 40℃; for 2.33h;
90%
Stage #1: glycoluril With dimethyl sulfoxide; sodium hydroxide at 40℃; for 1h;
Stage #2: 3-chloroprop-1-ene at 40℃; for 2.33h;
90%
Stage #1: glycoluril With sodium hydroxide In dimethyl sulfoxide at 40℃; for 1h;
Stage #2: 3-chloroprop-1-ene In dimethyl sulfoxide at 40℃; for 2.33333h;
90%
glycoluril
496-46-8

glycoluril

2,4,6,8-tetranitro-2,4,6,8-tetraazabicyclo<3.3.0>octane-3,7-dione
55510-03-7

2,4,6,8-tetranitro-2,4,6,8-tetraazabicyclo<3.3.0>octane-3,7-dione

Conditions
ConditionsYield
With nitric acid; dinitrogen pentoxide85%
With nitric acid; acetic anhydride 1.) 20 deg C, 30 min, 2.) 25 deg C - 30 deg C, 2 h;72%
With nitric acid; acetic anhydride at 0 - 35℃; for 4.16667h; Cooling with ice;
With nitric acid; acetic anhydride at 0 - 10℃; for 16h;
With nitric acid; acetic anhydride; zinc(II) chloride at 10 - 65℃; for 6.33333h; Reagent/catalyst; Temperature;
glycoluril
496-46-8

glycoluril

1,4-dinitroglycoluril
55510-04-8

1,4-dinitroglycoluril

Conditions
ConditionsYield
With dinitrogen pentoxide In carbon dioxide at 5 - 20℃; under 45004.5 - 60006 Torr; for 2h; Reagent/catalyst; Autoclave; liquid CO2;82%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one
83-07-8

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one

2,6-bis(1',5'-dimethyl-3'-oxo-2'-phenyl-2',3'-dihydro-1H-pyrazol-4'-yl)hexahydro-1H,5H-2,3,4,6,7,8-hexaazacyclopenta[def]fluorene-4,8-dione

2,6-bis(1',5'-dimethyl-3'-oxo-2'-phenyl-2',3'-dihydro-1H-pyrazol-4'-yl)hexahydro-1H,5H-2,3,4,6,7,8-hexaazacyclopenta[def]fluorene-4,8-dione

Conditions
ConditionsYield
Stage #1: formaldehyd; 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one In water at 20℃; Mannich Aminomethylation; Green chemistry;
Stage #2: glycoluril In water at 40℃; for 0.333333h; Green chemistry;
82%
glycoluril
496-46-8

glycoluril

N,N-bis(methoxymethyl)cyclohexan-1-amine

N,N-bis(methoxymethyl)cyclohexan-1-amine

2,6-dicyclohexylhexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-dione

2,6-dicyclohexylhexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-dione

Conditions
ConditionsYield
With samarium(III) chloride hexahydrate In ethanol; chloroform at 60℃; for 6h;81%
glycoluril
496-46-8

glycoluril

N,N-bis(methoxymethyl)-t-butylamine
74319-18-9

N,N-bis(methoxymethyl)-t-butylamine

2,6-di(tert-butyl)hexahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione

2,6-di(tert-butyl)hexahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione

Conditions
ConditionsYield
With samarium(III) chloride hexahydrate In ethanol; chloroform at 60℃; for 6h;78%
glycoluril
496-46-8

glycoluril

Bis(methoxymethyl)isopropylamin
66175-60-8

Bis(methoxymethyl)isopropylamin

2,6-diisopropylhexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-dione

2,6-diisopropylhexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-dione

Conditions
ConditionsYield
With samarium(III) chloride hexahydrate In ethanol; chloroform at 60℃; for 6h;75%
glycoluril
496-46-8

glycoluril

C6H15NO3

C6H15NO3

2,6-bis(2-hydroxyethyl)hexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-dione

2,6-bis(2-hydroxyethyl)hexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-dione

Conditions
ConditionsYield
With samarium(III) chloride hexahydrate In ethanol; chloroform at 60℃; for 6h;70%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

ethylenediamine
107-15-3

ethylenediamine

C14H22N8O2
93426-83-6

C14H22N8O2

Conditions
ConditionsYield
In methanol; water Heating;62%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

glycoluril dimer
375372-77-3

glycoluril dimer

Conditions
ConditionsYield
With hydrogenchloride In water at 50℃; for 48h;62%
glycoluril
496-46-8

glycoluril

acetic anhydride
108-24-7

acetic anhydride

A

1-acetylhydantoin
25046-23-5

1-acetylhydantoin

B

2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo<3,3,0>octan-3,7-dione
10543-60-9

2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo<3,3,0>octan-3,7-dione

Conditions
ConditionsYield
With 1-hydroxyethylene-(1,1-diphosphonic acid) for 0.5h; Reflux;A n/a
B 62%
glycoluril
496-46-8

glycoluril

acrylonitrile
107-13-1

acrylonitrile

1,3,4,6-tetrakis(2-cyanoethyl)glycoluril

1,3,4,6-tetrakis(2-cyanoethyl)glycoluril

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 120℃; for 5h;61%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

cucurbituril
80262-44-8

cucurbituril

Conditions
ConditionsYield
With sulfuric acid at 20 - 75℃;60%
With hydrogenchloride at 80 - 100℃; for 26.5h;31%
Stage #1: formaldehyd; glycoluril With hydrogenchloride In water Heating;
Stage #2: With sulfuric acid at 110 - 120℃;
21%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

Trimethylenediamine
109-76-2

Trimethylenediamine

C16H26N8O2
93426-84-7

C16H26N8O2

Conditions
ConditionsYield
In methanol; water Heating;54%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

glycylglycine
556-50-3

glycylglycine

(2-{6-[(Carboxymethyl-carbamoyl)-methyl]-4,8-dioxo-tetrahydro-2,3a,4a,6,7a,8a-hexaaza-cyclopenta[def]fluoren-2-yl}-acetylamino)-acetic acid

(2-{6-[(Carboxymethyl-carbamoyl)-methyl]-4,8-dioxo-tetrahydro-2,3a,4a,6,7a,8a-hexaaza-cyclopenta[def]fluoren-2-yl}-acetylamino)-acetic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 24h;52%
glycoluril
496-46-8

glycoluril

acetic anhydride
108-24-7

acetic anhydride

2,6-diacetyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione
28773-97-9

2,6-diacetyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions
ConditionsYield
With perchloric acid In 1,4-dioxane; water at 110℃;48%
With 1-hydroxyethylene-(1,1-diphosphonic acid) for 0.5h; Reagent/catalyst; Reflux;10%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

A

cucurbituril
80262-44-8

cucurbituril

B

cucurbit[5]uril

cucurbit[5]uril

C

cucurbit[7]uril

cucurbit[7]uril

D

cucurbit[8]uril

cucurbit[8]uril

Conditions
ConditionsYield
With sulfuric acid In water for 0.0125h; Microwave irradiation;A 45%
B 15%
C 20%
D 15%
With hydrogenchloride In water at 100 - 110℃; for 18h;
With sulfuric acid In water at 100℃; for 14h;
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

1-methyl-2,4,6,8-tetraazabicyclo[3.3.0]octan-3,7-dione
3720-96-5

1-methyl-2,4,6,8-tetraazabicyclo[3.3.0]octan-3,7-dione

A

C37H38N24O12

C37H38N24O12

B

cucurbituril
80262-44-8

cucurbituril

Conditions
ConditionsYield
With hydrogenchloride In water at 95℃; for 24h;A 14%
B 43%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

cucurbituril
80262-44-8

cucurbituril

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 17.5h;33.5%
With sulfuric acid In water at 75 - 100℃; for 36h;
With sulfuric acid at 75 - 100℃; for 36h;
Stage #1: formaldehyd; glycoluril With hydrogenchloride at 0℃; for 0.5h;
Stage #2: at 100℃; for 18h;
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

cucurbit[8]uril
259886-51-6

cucurbit[8]uril

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 17.5h;33.5%
formaldehyd
50-00-0

formaldehyd

glycoluril
496-46-8

glycoluril

A

cucurbituril
80262-44-8

cucurbituril

B

cucurbit[7]uril

cucurbit[7]uril

Conditions
ConditionsYield
With hydrogenchloride In water at 80 - 100℃; for 26.5h;A 33%
B 12%
With hydrogenchloride In water at 100℃;

496-46-8Relevant articles and documents

Understanding behaviour of vitamin-C guest binding with the cucurbit[6]uril host

Pandey, Shubham,Soni, Vineet Kumar,Choudhary, Ganpat,Sharma, Pragati R.,Sharma, Rakesh K.

, p. 387 - 394 (2017)

The present study describes non-covalent interaction and complexation behaviour of sodium ascorbate (SA) with cucurbit[6]uril (CB[6]) at neutral pH in aqueous Na2SO4 solution. The interaction behaviour is investigated using various analytical techniques like NMR, UV–Vis, fluorescence, TGA and DRS. The substantial increase in the intensity of emission and absorption spectra of sodium ascorbate is observed. The Benesi–Hildebrand evaluation method is used to determine the stoichiometry and equilibrium constant of the cucurbit[6]uril–sodium ascorbate complex, which suggested the 1:1 complex. Time-dependent 1H NMR, 13C CP MAS and CD studies also echoed non-covalent interaction between SA with CB[6].

Efficient method for the cycloaminomethylation of glycoluril

Wingard, Leah A.,Johnson, Eric C.,Sabatini, Jesse J.

, p. 1681 - 1682 (2016)

The efficient method for the cycloaminomethylation of glycoluril to yield 2,6-ditert-butylhexahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione is described. The material is synthesized employing water as the solvent, and is isolated by filtration. This is an improvement over the previous reported synthetic method, which relied on the use of samarium trichloride catalysis, as well as silica gel column chromatographic purification to obtain the target product.

Critical Parameters for Green Glycoluril Synthesis

Araki, K.,Bertolucci, M. M.,Demets, G. J. F.,Oliveira, A. de,Soares, R. S. B.,Souza, L. R. R.

, p. 739 - 742 (2021/06/02)

Abstract: We have studied the critical parameters of Micheletti’s glycoluril synthesisstarting from urea and glyoxal on a statistical and multivariate analysis basis[12]. The process ispotentially highly useful for scaling-up glycoluril production, and needs to beoptimized. We have come to a conclusion thatH3PO4 could be used as well asP4O10 giving high yields attemperature around 95°C, using glyoxal without prior purification. All reactionshave been completed in less than 25 min with the yield as high as 80% under theoptimized conditions.

Synthesis of Glycoluril using Urea Phosphate

Karpagalakshmi, K.,Lakshminarayanan, P.,Prakash, R.,Ramalakshmi, S.,Selvapalam, N.,Usha, G.,Yang, C.

, p. 1988 - 1992 (2022/01/24)

Abstract: Glycolurils are building blocks for the synthesis of cucurbiturils that are important host materials for several applications. Glycolurils are prepared conveniently by the condensation of 1,2-diketones with urea using an acid as catalyst. Herein, we report a facile method of synthesis of various glycolurils using urea phosphate and 1,2-diketones.

Dual-Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Zhang, Hao,Liang, Feng,Yang, Ying-Wei

supporting information, p. 198 - 205 (2019/12/12)

A 2D supramolecular organic framework (SOF) based on synthetic macrocycles has been constructed in water by a self-assembly strategy. Two new organic monomers of this SOF, possessing viologen and azobenzene functional groups, form a stimuli-responsive host–guest system upon cooperatively binding with cucurbit[8]uril rings. The reversible formation and dissociation of 2D SOF can be realized by the isomerization of azobenzene under ultraviolet and visible light. The light-responsive property of the SOF is highly reversible and stable for up to four cycles. Moreover, azoreductase produced by Escherichia coli can reduce the N=N double bond of azobenzene entities, resulting in fluorescence recovery of the system. As an excellent and effective fluorescent probe, the SOF can detect azoreductase activity for real-time monitoring of the growth process of Escherichia coli. The dual-stimuli responsive 2D SOF is envisioned to drive the development of responsive devices with complex functions.

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