2221-13-8

Basic information

• Product Name: 3-PHENYLIMIDAZOLIDINE-2,4-DIONE
• Synonyms: 3-PHENYLIMIDAZOLIDINE-2,4-DIONE;AKOS B029051;SALOR-INT L158313-1EA;N-phenyl-2,5-imidazolinedione;3-Phenylimidazolidine-2,4-dion;NSC20118;3-phenyl-2,4-imidazolidinedione(SALTDATA: FREE);3-Phenylhydantoin, 95%
• CAS NO: 2221-13-8
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Mol File: 2221-13-8.mol

Chemical Properties

• Melting Point: 194-195 °C (decomp)
• Boiling Point: 326.3°Cat760mmHg
• Flash Point: 151.1°C
• Appearance: White/Solid
• Density: 1.324g/cm³
• Vapor Pressure: 8.88E-05mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.07±0.70(Predicted)
• CAS DataBase Reference: 3-PHENYLIMIDAZOLIDINE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLIMIDAZOLIDINE-2,4-DIONE(2221-13-8)
• EPA Substance Registry System: 3-PHENYLIMIDAZOLIDINE-2,4-DIONE(2221-13-8)

Safety Data

• Hazardous Substances Data: 2221-13-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 2947, 1989 DOI: 10.1080/00397918908052688

InChI:InChI=1/C9H8N2O2/c12-8-6-10-9(13)11(8)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)

Upstream product

• 7684-19-7 N-[(phenylamino)carbonyl]glycine ethyl ester 
• 141-52-6 sodium ethanolate 
• 854893-40-6 N-ethoxycarbonyl-glycine anilide 
• 3016-39-5 2-(3-phenylureido)acetic acid 
• 7647-01-0 hydrogenchloride 
• 54001-50-2 2-(3-phenylureido)malonic acid diethyl ester 
• 80909-81-5 N-(N-phenylcarbamoyl-glycyl)-leucine 
• 104892-36-6 5-phenyl-hydantoic acid methyl ester 
• 64-10-8 phenyl carbamate 
• 56-40-6 glycine 
• 62-53-3 aniline 
• 461-72-3 2,4-imidazolidinedione 
• 66003-76-7 Diphenyliodonium triflate 
• 591-50-4 iodobenzene 

Downstream Products

• 85369-84-2 5-hydroxy-1-phenylimidazolidin-2-one 
• 33557-83-4 1-nitroso-3-phenyl-imidazolidine-2,4-dione 
• 947396-25-0 5-[(Z)-1-(2-chloro-4-hydroxyphenyl)methylidene]-3-phenylimidazolidine-2,4-dione 
• 947396-26-1 5-[(Z)-1-(2-bromo-4,5-dimethoxyphenyl)methylidene]-3-phenylimidazolidine-2,4-dione 
• 947396-27-2 5-[(Z)-1-(2-bromo-3,4,5-trimethoxyphenyl)methylidene]-3-phenylimidazolidine-2,4-dione 
• 947396-28-3 5-[(Z)-1-(2-chloro-5-nitrophenyl)methylidene]-3-phenylimidazolidine-2,4-dione 
• 74805-59-7 (Z)-1-phenyl-4-benzylideneimidazolidine-2,5-dione 
• 1174133-39-1 1-(2-phenoxypropanoyl)-3-phenylimidazolidine-2,4-dione 

Relevant articles and documents

STUDIES ON HYDANTOIN. PART 2. SUBSTITUENT EFFECTS IN 3-ARYLHYDANTOINS ON THE FORMATION OF ARYL ISOCYANATE IONS USING THE MASS-ANALYSED ION KINETIC ENERGY-DIRECT ANALYSIS OF DAUGHTER IONS

The unimolecular reaction of seven 3-arylhydantoins, relatively slow fragmentation in the free drift region, has been investigated by analysis of the mass-analysed ion kinetic energy (m.i.k.e.) spectrum using direct analysis of daughter ions (d.a.d.i.).Ar

Synthesis of Chiral Hydantoins and Thiazolidinediones via Iridium-Catalyzed Asymmetric Hydrogenation

Herein, we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand. The transformation shows good functional group tolerance, and gives the hydrogenated pro

N1- and N3-Arylations of Hydantoins Employing Diaryliodonium Salts via Copper(I) Catalysis at Room Temperature

Copper(I)-catalyzed N-arylation (both N1- and N3-) of hydantoins with diaryliodonium salts as aryl partners at room temperature is reported. The transformation allows diverse scopes on both hydantoins and diaryliodonium salts deliver

Design, synthesis and biological evaluation of imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as lymphoid-specific tyrosine phosphatase inhibitors

Lymphoid-specific tyrosine phosphatase (LYP), which exclusively exists in immune cells and down-regulates T cell receptor signaling (TCR), has becoming a potent target for various autoimmune diseases. Herein, we designed and synthesized imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as new LYP inhibitors. Among them, the cinnamic acids-based inhibitors (9p and 9r) displayed good LYP inhibitory activities (IC50 = 2.85–6.95 μM). Especially, the most potent inhibitor 9r was identified as competitive inhibitor (Ki = 1.09 μM) and bind LYP reversibly. Meanwhile, 9r exhibited better selectivity over other phosphatases than known LYP inhibitor A15. Furthermore, compound 9r could regulate TCR associated signaling pathway in Jurkat T cell.

Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts

A general Cu-catalyzed, regioselective method for the N-3-arylation of hydantoins is described. The protocol utilizes aryl(trimethoxyphenyl)iodonium tosylate as the arylating agent in the presence of triethylamine and a catalytic amount of a simple Cu-salt. The method is compatible with structurally diverse hydantoins and operates well with neutral aryl groups or aryl groups bearing weakly donating/withdrawing elements. It is also applicable for the rapid diversification of pharmaceutically relevant hydantoins.

Synthesis and herbicidal activity of 3-aryl-1-[2-(aryloxy)propanoyl] imidazolidine-2,4-diones

(Chemical Equation Presented) A series of novel 3-aryl-1-[2-(aryloxy) propanoyl]imidazolidine-2,4-diones were synthesized by the condensation of 3-aryl-imidazolidine-2,4-diones with 2-(aryloxy)propanoyl chlorides under mild conditions. Their structures we

Microwave-assisted solid-phase synthesis of hydantoin derivatives

A microwave-assisted synthesis of 3,5- and 1,3,5-substituted hydantoins starting from various resins for solid-phase combinatorial chemistry has been developed. The hydantoins were synthesized from pre-loaded resins with amino acids via treatment with isocyanate or phenylisocyanate and subsequent intramolecular cyclization. Both reactions were performed under microwave irradiation. We studied the cyclative cleavage leading to hydantoin compounds dependent on the nature of the amino acid and the nucleofuge properties of the resin.

Synthesis of imidazol[1,5-a]indole-1,3-diones from imidazolidene-2,4-diones

Copper and tributyltin hydride catalysed cyclization, through the N-aryl bond formation, of imidazolidine-2,4-diones (11-16,18) yielded imidazo[1,5-a]indole-1,3-diones (5-10) in high yields (72-100%). The ease of cyclization was found to be consistent with the normal halogen reactivity and the type of substituents. The highly substituted imidazole-2,4-dione 15 gave brominated 19 and tin incorporated heterocycles 20 when treated with copper bromide and tributyltin hydride, respectively.

Substituted 2-thioxoimidazolidin-4-ones and imidazolidine-2,4-diones as fatty acid amide hydrolase inhibitors templates

The demonstration of the essential role of fatty acid amide hydrolase (FAAH) in hydrolyzing endogenous bioactive fatty acid derivatives has launched the quest for the discovery of inhibitors for this enzyme. Along this line, a set of 58 imidazolidine-2,4-dione and 2-thioxoimidazolidin-4-one derivatives was evaluated as FAAH inhibitors. Among these compounds, 3-substituted 5,5′-diphenylimidazolidine-2,4-dione and 3-substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one derivatives were previously described as CB1 cannabinoid receptor ligands. In the present study, we synthesized several derivatives exhibiting interesting FAAH inhibitory activity and devoid of affinity for the CB1 and CB2 cannabinoid receptors. For instance, 3-heptyl-5,5′-diphenylimidazolidine- 2,4-dione (14) and 5,5′-diphenyl-3-tetradecyl-2-thioxo-imidazolidin-4-one (46) showed p/50 values of 5.12 and 5.94, respectively. In conclusion, it appears that even though several 3-substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one and 3-substituted 5,5′-diphenylimidazolidine-2,4-dione derivatives have been previously shown to behave as CB1 cannabinoid receptor ligands, appropriate substitutions of these templates can result in FAAH inhibitors devoid of affinity for the cannabinoid receptors.

A large gem-dimethyl effect in the cyclization of ω-phenylhydantoic acids: Computational modeling of the gem-dimethyl effect on the acid- or base-catalyzed cyclization of hydantoic acids and esters

The rates of the cyclization of methyl-substituted 5-phenylhydantoic acids were measured in acid solutions. A particularly strong gem-dimethyl effect (GDME) was observed with the N-methyl compounds amounting to an acceleration of six powers of ten for the 2,2,3-trimethyl derivative. The variations in the free energies of activation for the cyclization of hydantoic acids and esters were modeled by the strain energies of the tetrahedral intermediates and of the reactants calculated by the MM3 force field. The neutral tetrahedral intermediate T0 was used for reaction series involving acid catalysis and the negatively charged intermediate T- for base catalysis. Very good agreement with the experimental GDME was obtained for the acid-catalyzed cyclizations of the complete series of the N-methyl-substituted substrates, showing that the accelerations result from a greater strain increase in the reactants. The results with T- are closely parallel, indicating that the loss of GDME observed under base catalysis with 2,2,3-trimethylhydantoate esters is not due to intramolecular strain in T-. A linear correlation (slope 1.22, r=0.934) is obtained for a plot of the free energy variations against strain energies for the reaction series of 5-phenylhydantoic acids when the data for the strongly deviating parent acid is excluded. Excellent LFERs are obtained between the reaction series of esters and acids. The observed large rate enhancements induced by N-substituents explain the switches to cyclization routes in synthetic reactions. Copyright