Glycoluril Chemical Properties

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)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

1

HS Code 

29332990

MSDS

• Language:English Provider:Acetylenediurea
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Glycoluril Usage And Synthesis

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

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(496-46-8)Related Product Information

• 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