Glycoluril
Basic information
- CAS
496-46-8- Standard SMILES
O=C1NC2NC(=O)NC2N1- InChIKey
VPVSTMAPERLKKM-UHFFFAOYSA-N- Molecular formula
- C4H6N4O2
- Average molar mass
- 142.12 g/mol
- Monoisotopic mass
- 142.04907545
Overview
Glycoluril is an azabicycloalkane and a member of ureas.
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 carbamide1,3,3a,4,6,6a-hexahydroimidazo[4,5-d]imidazole-2,5-dioneDTXSID6031380Imidazo[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)-dione(3as,6as)-octahydroimidazo(4,5-d)imidazolidine-2,5-dione
Show more names
5(1HNSC 2765GlycourilGlycolueilGansu urea
1,3,3a,4,6,6a-hexahydroimidazo(4,5-d)imidazole-2,5-dioneRefChem:143920DTXCID4011380AcetyleneureaGlyoxaldiureineAcetylenediureaGlyoxalbiuretGlyoxaldiurene
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
- Formal charge
- 0
- Complexity
- 165
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
DrugsPharmaceuticals -> Listed in ZINC15
Physical Description
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
- solubility
- 15 g/l · 15g/l
- form
- powder to crystal
- pka
- 12.91 · 12.91±0.20(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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.
Hazard information
Regulatory Information
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)
REACH registered substance: Perhydroimidazo[4,5-d]imidazole-2,5-dione (EC: 207-821-5)
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
Chemistry & industry
Uses & manufacturing
Uses
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
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesOther
General Manufacturing Information
Plastics Material and Resin Manufacturing
Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-: ACTIVE
Applications
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
Upstream raw materials
Related reactions
5 records
Compound notes
Loading…