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Glycoluril

Glycoluril structure

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

Molecular Weight:: 142.12

MDL Number:: MFCD00005539

MOL File:: 496-46-8.mol

MSDS File:: SDS

Last updated:2025-07-24 18:13:49

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Glycoluril 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
pka	12.91±0.20(Predicted)
form	powder to crystal
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)
FDA UNII	U9H2W4OS13
NIST Chemistry Reference	Glycoluril(496-46-8)
EPA Substance Registry System	Glycoluril (496-46-8)
UNSPSC Code	12352100
NACRES	NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS06

Signal word

Danger

Hazard statements

H301+H331-H315-H319-H335

Precautionary statements

P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P332+P313+P362+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501

Hazard Codes

Risk Statements

Safety Statements

24/25

WGK Germany

HS Code

29332990

NFPA 704

	0
1		0

Glycoluril price More Price(21)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	G7305	Glycoluril 97%	496-46-8	5g	$42.75	2025-07-31	Buy
Sigma-Aldrich	G7305	Glycoluril 97%	496-46-8	100g	$148	2025-07-31	Buy
TCI Chemical	G0243	Glycoluril >98.0%(N)	496-46-8	25g	$53	2025-07-31	Buy
Usbiological	278248	Glycouril	496-46-8	100g	$333	2021-12-16	Buy
TRC	G645900	Glycoluril	496-46-8	1g	$120	2021-12-16	Buy

Product number	Packaging	Price	Buy
G7305	5g	$42.75	Buy
G7305	100g	$148	Buy
G0243	25g	$53	Buy
278248	100g	$333	Buy
G645900	1g	$120	Buy

Glycoluril Chemical Properties,Uses,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

For derivatives glycoluril, glycoluril resins

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.

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

1,2-Ethenediylbis(oxy) (9CI) Urea Water Sulfuric acid

Preparation Products

CUCURBIT(7)URIL PARABANIC ACID CUCURBITURIL

Glycoluril Suppliers

Global( 281)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21622	55
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29855	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	49733	58
SIMAGCHEM CORP	+86-5922680277 +86-13806087780	sale@simagchem.com	China	17346	58
Hefei TNJ Chemical Industry Co.,Ltd.	+86-0551-65418671 +8618949823763	sales@tnjchem.com	China	34563	58
Alfa Chemistry		info@alfa-chemistry.com	United States	2344	58
Baoji Guokang Bio-Technology Co., Ltd.	0917-3909592 13892490616	gksales1@gk-bio.com	China	9249	58
CD Chemical Group Limited	+8615986615575	info@codchem.com	China	20342	58
changzhou huayang technology co., ltd	+8615250961469	2571773637@qq.com	China	9647	58
Shaanxi Didu New Materials Co. Ltd	+86-89586680 +86-13289823923	1026@dideu.com	China	8982	58

Supplier	Advantage
Henan Tianfu Chemical Co.,Ltd.	55
career henan chemical co	58
CONIER CHEM AND PHARMA LIMITED	58
SIMAGCHEM CORP	58
Hefei TNJ Chemical Industry Co.,Ltd.	58
Alfa Chemistry	58
Baoji Guokang Bio-Technology Co., Ltd.	58
CD Chemical Group Limited	58
changzhou huayang technology co., ltd	58
Shaanxi Didu New Materials Co. Ltd	58

View Lastest Price from Glycoluril manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2025-04-04	Glycoluril 496-46-8	US $0.00-0.00 / KG	1KG	98%	1ton	Henan Aochuang Chemical Co.,Ltd.
2021-07-13	Glycoluril 496-46-8	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd
2021-07-10	Glycoluril 496-46-8	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd

Glycoluril
496-46-8
US $0.00-0.00 / KG
98%
Henan Aochuang Chemical Co.,Ltd.

Glycoluril
496-46-8
US $15.00-10.00 / KG
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

Glycoluril
496-46-8
US $15.00-10.00 / KG
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

Glycoluril Spectrum

Glycoluril(496-46-8)MS Glycoluril(496-46-8)¹HNMR Glycoluril(496-46-8)IR1 Glycoluril(496-46-8)IR2 Glycoluril(496-46-8)Raman

496-46-8(Glycoluril)Related 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

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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> 496-46-8 Building Blocks Others Heterocyclic Building Blocks N-Containing Building Blocks Chemical Synthesis Heterocyclic Building Blocks N-Containing Others Heterocyclic Compounds