ChemicalBook > CAS DataBase List > Glycoluril

Glycoluril

Product Name: Glycoluril
CAS No.: 496-46-8
Chemical Name: Glycoluril
Synonyms: TETRAHYDROIMIDAZO[4,5-D]IMIDAZOLE-2,5(1H,3H)-DIONE;Acetylene carbamide;5(1H;NSC 2765;Glycouril;Glycolueil;Glycoluril;Gansu urea;Glyoxalbiuret;ACETYLENEUREA
CBNumber: CB8461401
Molecular Formula: C4H6N4O2
Formula Weight: 142.12
MOL File: 496-46-8.mol

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Glycoluril Property

Melting point:: >300 °C (lit.)
Boiling point:: 259.66°C (rough estimate)
Density: 1.4926 (rough estimate)
vapor pressure: 0Pa at 25℃
refractive index: 1.8500 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: 15g/l
form: powder to crystal
pka: 12.91±0.20(Predicted)
color: White to Almost white
Water Solubility: 1.8g/L at 20℃
Merck: 14,93
BRN: 128826
LogP: -3.28
CAS DataBase Reference: 496-46-8(CAS DataBase Reference)
NIST Chemistry Reference: Glycoluril(496-46-8)
EPA Substance Registry System: Glycoluril (496-46-8)

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Safety

Hazard Codes: Xn
Risk Statements: 22
Safety Statements: 24/25
WGK Germany: 1
HS Code: 29332990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: G7305
Product name: Glycoluril
Purity: 97%
Packaging: 5g
Price: $42.75
Updated: 2025/07/31

Sigma-Aldrich

Product number: G7305
Product name: Glycoluril
Purity: 97%
Packaging: 100g
Price: $148
Updated: 2025/07/31

TCI Chemical

Product number: G0243
Product name: Glycoluril
Purity: >98.0%(N)
Packaging: 25g
Price: $53
Updated: 2025/07/31

Usbiological

Product number: 278248
Product name: Glycouril
Packaging: 100g
Price: $333
Updated: 2021/12/16

TRC

Product number: G645900
Product name: Glycoluril
Packaging: 1g
Price: $120
Updated: 2021/12/16

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Glycoluril Chemical Properties,Usage,Production

Chemical Properties

WHITE TO VERY SLIGHTLY YELLOW CRYSTALLINE POWDER

Uses

Reactant involved in synthesis of:• ;Glycouril hexamers and monofunctionalized cucurbit[6]uril derivatives1,2,3• ;N-chloro compounds from trichloroisocyanuric acid4• ;Glycouril trimers5

Uses

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.

Uses

For derivatives glycoluril, glycoluril resins

Definition

ChEBI: Glycoluril is an azabicycloalkane and a member of ureas.

Flammability and Explosibility

Not classified

Agricultural Uses

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

Synthesis

131543-46-9

57-13-6

496-46-8

To a 500 mL three-necked round-bottomed flask equipped with a stirrer was added 100 mL of deionized water, glyoxal (20 g, 0.345 mol, 1.00 eq., 50 mL of a 40 wt% aqueous solution) and urea (51.7 g, 0.862 mol, 2.50 eq.). The reaction mixture was heated to 90°C and stirred for 5 minutes. Concentrated sulfuric acid (4 mL) was slowly added dropwise over 5 minutes, and a white solid formed within 10 minutes after the drop was completed. Stirring of the reaction mixture was continued for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature and 50% aqueous sodium hydroxide was added dropwise until the pH was adjusted to 14. Stirring was stopped and the reaction mixture was cooled to 0°C. The suspension was separated by vacuum filtration through a Brinell's funnel and the solids were washed with cold water (2 x 500 mL). The solid was transferred to a Brinell funnel and dried under suction for 3 h. Subsequently, it was transferred to a 700 mL beaker and dried at 80°C for 16 h. Glycuronium (1) was obtained as an off-white powder in 45.0 g (0.304 mol, 92% yield). Melting point: 335.19°C; IR (cm^-1): 3182.5 (s), 1677.0 (s); 1H NMR (90 MHz, DMSO-d6): δ 7.13 (s, 4H, -NH), 5.23 (s, 2H, N-CH-N).

References

[1] Tetrahedron Letters, 2016, vol. 57, # 15, p. 1681 - 1682
[2] Patent: WO2014/166347, 2014, A1. Location in patent: Page/Page column 13
[3] Patent: WO2015/143974, 2015, A1. Location in patent: Page/Page column 15
[4] J. Gen. Chem. USSR (Engl. Transl.), 1991, vol. 61, # 12, p. 2581 - 2582
[5] Zhurnal Obshchei Khimii, 1991, vol. 61, # 12, p. 2778 - 2780

Glycoluril Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Glycoluril manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: Glycoluril 496-46-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98
Supply Ability: 10000KGS
Release date: 2025-11-13

Henan Aochuang Chemical Co.,Ltd.

Product: Glycoluril 496-46-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2022-09-29

Zhuozhou Wenxi import and Export Co., Ltd

Product: Glycoluril 496-46-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-11

496-46-8, GlycolurilRelated Search:

Imidazole CUCURBITURIL 1,3,4,6-Tetrakis(methoxymethyl)glycoluril N,N',N'',N'''-Tetraacetylglycoluril 1,3,4,6-TETRACHLORO-3ALPHA,6ALPHA-DI-PHENYLGLYCOURIL mebikar Tetramethylol acetylenediurea 3a,6a-Diphenyloctahydroimidazo[4,5-d]imidazole-2,5-dione 1,3,4,6-Tetrachlorotetrahydroimidazo(4,5-d)imidazole-2,5(1H,3H)-dione Acetylene Glycoluril (4,6-DIMETHYL-2,5-DIOXO-HEXAHYDRO-IMIDAZO-[4,5-D]IMIDAZOL-1-YL)-ACETIC ACID 1,4-diacetyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione 4-(2,5-DIOXO-HEXAHYDRO-IMIDAZO[4,5-D]IMIDAZOL-1-YL)-BUTYRIC ACID 2-(2,5-DIOXO-HEXAHYDRO-IMIDAZO[4,5-D]IMIDAZOL-1-YL)-4-METHYLSULFANYL-BUTYRIC ACID 1,3,4,6-TETRAKIS(BUTOXYMETHYL)GLYCOLURIL, TECH. HEXAHYDRO-2,6-BIS(2,2,6,6-TETRAMETHYL-4-PIPERIDINYL)-1H,4H,5H,8H-2,3A,4A,6,7A,8A-HEXAAZACYCLOPENTA[DEF]FLUORENE-4,8-DIONE SPECS AA-516/25012248

5-d]imidazole-2,5(1h,3h)-dione,tetrahydro-imidazo[

5-d]imidazole-2,5(1H,3H)-dione,tetrahydro-Imidazo[4

Acetylene carbamide

Acetylenediureine

Diurea glyoxalate

Glyoxalbiuret

Glyoxaldiureine

Glyoxaldiurene

Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-

Tetrahydroimidaz(d)imidazole-2,5-(1H,3H)-dione

ACETYLENEDIUREA

ACETYLENE DIUREIN

ACETYLENEUREA

Octahydroimidazo[4,5-d]imidazolidine-2,5-dione

ACETYL CARBAMIDE

TETRAHYDROIMIDAZO[4,5-D]IMIDAZOLE-2,5(1H,3H)-DIONE

TIMTEC-BB SBB004149

di-1,2-ureyleneethane

perhydroimidazo(4,5-d)imidazole-2,5-dione

Acetyleneurea;Acetylene carbamide;Acetylenediureine;Glycolueil;Glyoxaldiureine

Glycolueil

Glycouril

Glycoluril, 98+%

Perhydroimidazo[4,5-d]imidazol-2,5-dion

Glycouril, HPLC 98%

Glycoluril: (Acetyleneurea)

1,3,3a,4,6,6a-Hexahydroimidazo[4,5-d]imidazole-2,5-dione

3a,4,5,6,6a-Pentahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

3a,4,6,6a-Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Glycoluril

Gansu urea

Glycoluril 0.2

ACETYLENEDIUREA FOR SYNTHESIS

Acetyleneurea Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

NSC 2765

Tetrahydroimidazo[4,5-d]imidazole-2,5-dione

5(1H

Glycoluril 97%

glycoluril:tetrahydroimidazo(4,5-d)IMIDAZOLE-2,5-(1h,3h)-dione

Glycoluril p Humide

Glycoluril p Standard Dry

Glycoluril&gt

496-46-8

Building Blocks

Others

Heterocyclic Building Blocks

N-Containing

Building Blocks

Chemical Synthesis

Heterocyclic Building Blocks

N-Containing

Others

Heterocyclic Compounds