461-72-3

Basic information

• Product Name: Hydantoin
• Synonyms: 2,4-IMIDAZOLIDINEDIONE;2,4-IMIDAZOLINEDIONE;2,4-(3H,5H)-IMIDAZOLEDIONE;Imidazolidine-2,4-dione;HYDANTOIN;GLYCOLYLUREA;2-hydroxy-2-imidazolin-4(or5)-on;2-Imidazolin-4(or 5)-one, 2-hydroxy-
• CAS NO: 461-72-3
• Molecular Formula: C₃H₄N₂O₂
• Molecular Weight: 100.08
• EINECS: 207-313-3
• Product Categories: Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;Chemical Amines;Amines;Heterocycles;Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 461-72-3.mol
• Article Data: 57

Chemical Properties

• Melting Point: 218-220 °C(lit.)
• Boiling Point: 187.47°C (rough estimate)
• Flash Point: 102.8°C
• Appearance: White to light yellow/Fine Powder
• Density: 1.4457 (rough estimate)
• Vapor Pressure: 0.00448mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: SLIGHTLY SOLUBLE
• PKA: pKa 9.1 (Uncertain)
• Water Solubility: SLIGHTLY SOLUBLE
• Merck: 14,4760
• BRN: 110598
• CAS DataBase Reference: Hydantoin(CAS DataBase Reference)
• NIST Chemistry Reference: Hydantoin(461-72-3)
• EPA Substance Registry System: Hydantoin(461-72-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26
• WGK Germany: 3
• RTECS: MT8210000
• TSCA: Yes
• Hazardous Substances Data: 461-72-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hydantoin is used as a reactant for the synthesis of several pharmaceutical agents, including:
1. N-benzyl aplysinopsin analogs, which are potential anticancer agents.
2. D-glutamic acid-based inhibitors, which may have therapeutic applications.
3. Antidiabetic chromonyl-2,4-thiazolidinediones, which could be used to manage diabetes.
4. GSK-3β inhibitors with brain permeability, potentially useful in treating neurological disorders.
5. Thiazolidinedione derivatives as 15-PGDH inhibitors, which may have implications in inflammatory diseases.
Additionally, Hydantoin is used as a reactant for the synthesis of:
6. Radio-sensitizing agents, which can enhance the effectiveness of radiation therapy in cancer treatment.
Used in Enzyme Research:
Hydantoin has been utilized as a substrate at specific conditions (40 °C and pH 9.0) to determine the D-hydantoinase activity in adzuki bean extract, which is essential for understanding enzyme function and potential applications in biotechnology and medicine.

InChI:InChI=1/C3H2N2O2/c6-2-1-4-3(7)5-2/h1H,(H,5,6,7)

Upstream product

• 97-59-6 Allantoin 
• 508-37-2 uroxanate 
• 64-17-5 ethanol 
• 57-13-6 urea 
• 7580-59-8 dioxosuccinic acid 
• 590-28-3 potassium cyanate 
• 56-40-6 glycine 
• 120-89-8 parabanic acid 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 20334-64-9 disodium diketosuccinic acid 
• 67-56-1 methanol 
• 3720-97-6 4,5-dihydroxy-2-imidazolidinone 
• 54896-74-1 (S)-N-carbamoylmethionine 

Downstream Products

• 165605-28-7 1-<2-(4-nitrophenyl)ethyl>imidazolidine-2,5-dione 
• 136197-77-8 3-(4-Chlorobenzyl)imidazolidine-2,4-dione 
• 699-51-4 1,3-diazaspiro[4.4]nonane-2,4-dione 
• 56-40-6 glycine 
• 3775-01-7 5-benzylidenehydantoin 
• 117751-51-6 (RS)-5-((SR)-α-hydroxy-benzyl)-imidazolidine-2,4-dione 
• 117751-51-6 (RS)-5-((RS)-α-hydroxy-benzyl)-imidazolidine-2,4-dione 
• 90771-20-3 (Z)-5-(2-hydroxybenzylidene)imidazolidine-2,4-dione 
• 109754-07-6 (5Z)-5-(4-methylbenzylidene)imidazolidine-2,4-dione 
• 16935-43-6 1,3-dibenzylimidazolidine-2,4-dione 
• 10040-86-5 (Z)-5-(4-chlorobenzylidene)imidazolidine-2,4-dione 
• 137920-46-8 5-[1-(2,6-Dichloro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 

Relevant articles and documents

Regioselective reactions of N-(carboxyalkyl)- and N-(aminoethyl)ureas with glyoxal and 1,2-dioxo-1,2-diphenylethane

Regioselective reactions of N-(carboxyalkyl)ureas (ureido acids) and N-(aminoethyl)ureas with 1,2-dioxo-1,2-diphenylethane (benzyl) and glyoxal are studied in detail. The structure of the reactants affects the reaction regioselectivity. Acid-catalyzed rea

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

The reaction of 4,5-dihydroxyimidazolidin-2-ones with chiral (S)-N, N'-dicarbamoyl-α,ω,-amino acids occurs as one-pot double cyclisation under acid catalysis to give the corresponding glycoluriles with (S)-N-hydantoinoalkyl substituents.

The first synthesis of assemblies of imidazolidine rings by α-ureidoalkylation of imidazolidin-2-one with 4,5-dihydroxyimidazolidin-2- ones

The synthesis of assemblies of imidazolidine rings has been developed based on the α-ureidoalkylation of imidazolidin-2-one with 4,5- dihydroxyimidazolidin-2-ones.

α-Ureidoalkylation of thiosemicarbazide and aminoguanidine

Optimum conditions for the targeted synthesis of 5,7-dialkyl-3- thioxoperhydroimid-azo[4,5-e][1,2,4]triazin-6-ones, 4,5-bis(3- thiosemicarbazido(guanidinoamino))imidazolidin-2-ones, and 1,3-dialkyl-4- (guanidinoimino)imidazolidin-2-ones by α-ureidoalkylation of thiosemicarbazide or aminoguanidine were found. A novel conglomerate in the series of imidazolidin-2-one derivatives was detected: 4,5-bis(guanidinoamino)- 1,3-dimethylimid-azolidin-2-one dihydrochloride dihydrate. Springer Science+Business Media, Inc. 2006.

Efficient Synthesis of Tetraacetylglycoluril in the Presence of Phosphorus-Containing Catalysts

Abstract: The effect of phosphorus-containing catalysts, namely phosphorous acid, phosphoric acid, diethyl hydrogen phosphite, and 1-hydroxyethane-1,1-diyldiphosphonic acid (HEDP), in the synthesis of tetraacetylglycoluril by acylation of glycoluril with acetic anhydride at 140°C has been studied. The use of 4 equiv of phosphorous or phosphoric acid with respect to glycoluril has been found to be the most appropriate for achieving the maximum yield (95–98%), and specific effect of HEDP leads to N-acetylation–deacetylation of substrates. The positive effect of phosphorus acids on the formation of tetraacetylglycoluril may be related to not only their catalytic action but also the ability to solubilize the substrate.

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2-dicarbonyl compounds using etidronic acid as a “green catalyst”

Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as “Green catalyst.” So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80°C-90°C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.

Method for continuous co-production of glycine and hydantoin

A method for continuous co-production of glycine and hydantoin is provided. The method includes subjecting an amino source, a carbon source, water and hydroxyacetonitrile to a hydantoin synthesizing reaction in a shell-and-tube reactor to obtain a first reaction product; feeding the first reaction product into a flash column for treatment to obtain a first treatment product; dividing the first treatment product into a first portion and a second portion; subjecting the first portion to first concentration treatment in an evaporator to obtain a first concentrate; reacting the first concentrate with concentrated sulfuric acid to obtain a second reaction product including hydantoin; subjecting the second portion to hydantoin decomposition in a tank series reactor to obtain a third reaction product including glycine. Compared with the prior art, the method realizes the continuous co-production of the glycine and the hydantoin.

Method for synthesizing 1-isopropyl benzamide-3-(3,5-dichlorophenyl)hydantoin

The invention discloses a method for synthesizing 1-isopropyl benzamide-3-(3,5-dichlorophenyl)hydantoin. The method comprises the following steps: reacting by virtue of chloroacetyl chloride and urea in the presence of a catalyst, so as to prepare hydantoin; reacting by virtue of hydantoin and 1,3,5-trichlorobenzene in the presence of triethylamine, so as to prepare 3,5-dichlorophenyl-hydantoin; and reacting by virtue of 3,5-dichlorophenyl-hydantoin and isopropyl isocyanate in the presence of a catalyst, so as to prepare 1-isopropyl benzamide-3-(3,5-dichlorophenyl)hydantoin. According to a reaction route utilized in the method, an expensive raw material 3,5-dichloroaniline and a highly toxic raw material phosgene are not adopted, and the method has the characteristics of few reaction steps, less waste gas, wastewater and industrial residue, high product yield and good product quality as well as obvious economic and social benefits.

Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound

The invention belongs to the field of medicines and in particular relates to a compound with the structure of a formula I, a stereomer of the compound or pharmaceutically acceptable salts of the compound as well as a preparation method of the compound and application of the compound to preparation of anti-tumor medicines. A pharmacological experiment result shows that the compound can be used for inhibiting the activity of NEDD8 kinase and has the inhibition effect on proliferation of a plurality of types of tumor cells, so that the compound can be used as an NEDD8 kinase activity inhibitor for preparing the anti-tumor medicines. The formula I is shown in the description.

Meteorites as catalysts for prebiotic chemistry

From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.