Glycoluril

HCID 62347CAS 496-46-8
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C1NC2NC(=O)NC2N1
InChIKey
VPVSTMAPERLKKM-UHFFFAOYSA-N
Molecular formula
C4H6N4O2
Average molar mass
142.12 g/mol
Monoisotopic mass
142.04907545

Names & identifiers

Preferred name
Glycoluril
IUPAC
1,3,3a,4,6,6a-hexahydroimidazo[4,5-d]imidazole-2,5-dione
English name
Glycoluril
Molecular formula
C4H6N4O2
Molecular weight
142.12

Names & synonyms

Glycoluril496-46-8tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dioneAcetylenediureineAcetylene carbamideDTXSID60313801,3,3a,4,6,6a-hexahydroimidazo[4,5-d]imidazole-2,5-dioneImidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-CHEBI:42946Imidazo(4,5-d)imidazole-2,5(1H,3H)-dione, tetrahydro-Tetrahydroimidazo(4,5-d)imidazole-2,5(1H,3H)-dione1,3,3a,4,6,6a-hexahydroimidazo(4,5-d)imidazole-2,5-dione
Show more names
5(1HNSC 2765GlycourilGlycolueilGansu urea
RefChem:143920DTXCID4011380(3as,6as)-octahydroimidazo(4,5-d)imidazolidine-2,5-dioneAcetyleneureaGlyoxaldiureineAcetylenediureaGlyoxalbiuretGlyoxaldiurene

Database identifiers

CAS
496-46-8
PubChem CID
62347
DTXSID
DTXSID6031380
ChEMBL
CHEMBL3182837
ChEBI
CHEBI:42946
UNII
U9H2W4OS13
EC Number
207-821-5
Nikkaji
J1.042.644H、J2.599B

Properties

Computed structural properties

XLogP
-1.6
Topological polar surface area
82.3 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
10

Experimental & physicochemical properties

Physical Description · 2 items

Other Solid; Liquid

Solid; [Merck Index] Beige powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
300 °C · >300 °C (lit.)
Boiling point
259.66 °C · 259.66°C (rough estimate)
Density
1.4926 · 1.4926 (rough estimate)
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.85 · 1.8500 (estimate)
storage temp.
Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 14.9% (7 of 47) of reports.

Warning

H302 (85.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 2 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 7 of 47 reports by companies.；There is 1 notification provided by 40 of 47 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

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

Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24399；Status: Active Update: 11-01-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/18710

Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryMay cause irritation; Harmful by ingestion; [Sigma-Aldrich MSDS] See Urea.
Hazard Classes and CategoriesAcute Tox. 4 (85.1%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

30 [mg/m3]

330 [mg/m3]

2000 [mg/m3]

Toxicology

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Regulatory information

Regulatory Information · 4 items

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

Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24399；Status: Active Update: 11-01-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/18710

Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Safety data

wgk
1
tsca
TSCA listed
hs_code
29332990
risk_code
22
Signal word
Danger
Symbol(GHS)
GHS06

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Glycoluril can be used to make Cucurbiturils. They have been used by chemists for various applications, including drug delivery, asymmetric synthesis, molecular switching, and dye tuning.

U.S. Production2023: 75,000 - <500,000 lb；2022: 500,000 - <1,000,000 lb；2021: 75,000 - <500,000 lb；2020: 75,000 - <500,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesOther
General Manufacturing Information · 2 items

Plastics Material and Resin Manufacturing

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

Applications · 3 items

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

UsesGlycoluril 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.

UsesFor derivatives glycoluril, glycoluril resins

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]

Additional notes

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

Related reactions

5 records
New reaction record

Linked notes

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