Hydantoin

Base Information

• Chemical Name: Hydantoin
• CAS No.: 461-72-3
• Deprecated CAS: 345341-10-8,1394977-74-2
• Molecular Formula: C3H4N2O2
• Molecular Weight: 100.077
• Hs Code.: 2933.21
• European Community (EC) Number: 207-313-3
• NSC Number: 9226
• UNII: I6208298TA
• DSSTox Substance ID: DTXSID1052111
• Nikkaji Number: J2.588G
• Wikipedia: Hydantoin
• Wikidata: Q418082
• RXCUI: 1721294
• Pharos Ligand ID: VRC4FF9N4ZH5
• Metabolomics Workbench ID: 51389
• ChEMBL ID: CHEMBL122334
• Mol file: 461-72-3.mol

Synonyms:Hydantoin;Hydantoins;Imidazolidine 2,4 Diones;Imidazolidine-2,4-Diones

Chemical Property of Hydantoin

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.00448mmHg at 25°C
• Melting Point: 218-220 °C(lit.)
• Refractive Index: 1.702
• Boiling Point: 246.4°C at 760 mmHg
• PKA: pKa 9.1 (Uncertain)
• Flash Point: 102.8°C
• PSA: 58.20000
• Density: 1.357 g/cm³
• LogP: -0.51660
• Storage Temp.: Store below +30°C.
• Solubility.: SLIGHTLY SOLUBLE
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.027277375
• Heavy Atom Count: 7
• Complexity: 120

Purity/Quality:

99%min ^*data from raw suppliers

Hydantoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: C1C(=O)NC(=O)N1
• Uses: Reactant for synthesis of: N-benzyl aplysinopsin analogs as anticancer agents1 D-glutamic acid based inhibitors2 Antidiabetic chromonyl-2,4-thiazolidinediones3 GSK-3β inhibitors with brain permeability4 Thiazolidinedione derivatives as 15-PGDH inhibitors5 Radio-sensitizing agents6 The product has been used as a substrate (at 40 °C and pH 9.0) to determine the D-hydantoinase activity in adzuki bean extract.

Technology Process of Hydantoin

There total 133 articles about Hydantoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

chloroacetyl chloride (79-04-9) + urea (57-13-6) → 2,4-imidazolidinedione (461-72-3)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; Solvent; Cooling with ice;

Reference yield: 86.0%

1-acetyl-2-thiohydantoin (584-26-9) → 2,4-imidazolidinedione (461-72-3)

Guidance literature:

With water; chloroacetic acid; for 2h; Reflux;

Reference yield: 84.0%

2-thiohydantoin (503-87-7) → 2,4-imidazolidinedione (461-72-3)

Guidance literature:

With tetrabutylammonium periodite; In dichloromethane; acetonitrile; at 20 ℃; for 2h;

DOI:10.1007/s00706-005-0289-8

upstream raw materials:

Allantoin

4,5-dihydroxy-2-imidazolidinone

parabanic acid

cyanomethylurea

Downstream raw materials:

5-(3-indolylmethylene)hydantoin

5-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylmethylene)-imidazolidine-2,4-dione

5-(2,4,5-trimethoxy-benzylidene)-imidazolidine-2,4-dione

1-acetyl-5-(2-benzylmercapto-1-phenyl-1H-imidazol-4-ylmethylene)-imidazolidine-2,4-dione

Refernces

• 1、 Chikunov, Il'ya E.,Kravchenko, Angelina N.,Belyakov, Pavel A.,Lebedev, Oleg V.,Makhova, Nina N.. "Synthesis of (S)-N-hydantoinoalkylglycoluriles by one-pot double cyclisation of chiral α,ω-diureido acids under the action of 4,5-dihydroxyimidazolidin-2-ones". . p. 67 - 69. Retrieved 2005.
• 2、 Sigachev,Kravchenko,Belyakov,Lebedev,Makhova. "α-Ureidoalkylation of thiosemicarbazide and aminoguanidine". . p. 865 - 872. Retrieved 2006.
• 3、 Bakibaev, Abdigali A.,Uhov, Artur,S. Malkov, Victor,Yu. Panshina, Svetlana. "Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2-dicarbonyl compounds using etidronic acid as a “green catalyst”". . p. 4262 - 4270. Retrieved 2020/10/02.
• 4、 -. "Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound". Paragraph 0095; 0096; 0097. . Retrieved 2016/10/10.