95378-36-2

Basic information

• Product Name: DIETHYL 5-HYDANTOYLPHOSPHONATE
• Synonyms: DIETHYL 5-HYDANTOYLPHOSPHONATE;Diethyl5-hydantoylphosphonate,96%;Diethyl 2,4-dioxoimidazolidine-5-phosphonate;Diethyl (2,5-dioxo-4-imidazolidinyl)phosphonate
• CAS NO: 95378-36-2
• Molecular Formula: C₇H₁₃N₂O₅P
• Molecular Weight: 234.15
• Mol File: 95378-36-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 159-161°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.35g/cm³
• Refractive Index: 1.485
• BRN: 4809527
• CAS DataBase Reference: DIETHYL 5-HYDANTOYLPHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 5-HYDANTOYLPHOSPHONATE(95378-36-2)
• EPA Substance Registry System: DIETHYL 5-HYDANTOYLPHOSPHONATE(95378-36-2)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 95378-36-2(Hazardous Substances Data)

Usage

General Description

DIETHYL 5-HYDANTOYLPHOSPHONATE is a chemical compound that is used as a reagent in various organic synthesis reactions. It is a phosphonate ester featuring a hydantoin ring, making it a valuable building block in the production of pharmaceuticals, agrochemicals, and other fine chemicals. DIETHYL 5-HYDANTOYLPHOSPHONATE is known for its versatile reactivity and it is often used as a precursor in the synthesis of chiral organophosphorus compounds. It may also have potential applications in medicinal chemistry due to its structural resemblance to hydantoin-based anticonvulsant drugs. However, it is important to handle this compound with caution as it can be hazardous if mishandled or improperly used.

InChI:InChI=1/C7H13N2O5P/c1-3-13-15(12,14-4-2)6-5(10)8-7(11)9-6/h6H,3-4H2,1-2H3,(H2,8,9,10,11)

Upstream product

• 461-72-3 2,4-imidazolidinedione 
• 122-52-1 triethyl phosphite 
• 79428-78-7 2-Amino-2-(diethoxyphosphoryl)essigsaeure-ethylester 
• 173904-10-4 5-bromohydantoin 

Downstream Products

• 137920-41-3 5-(3-hydroxy-benzylidene)-imidazolidine-2,4-dione 
• 137920-35-5 N-{2-[2,5-Dioxo-imidazolidin-(4Z)-ylidenemethyl]-phenyl}-acetamide 
• 137920-33-3 5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 137920-34-4 5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 135352-52-2 5-[1-(2,4,6-Trimethoxy-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 135352-59-9 5-[2,2,2-Trifluoro-1-phenyl-eth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 137920-47-9 5-[1-(2,4,6-Trimethyl-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 135352-61-3 5-(1-Benzyl-piperidin-4-ylidene)-imidazolidine-2,4-dione 
• 31615-89-1 2-(2,5-dioxo-imidazolidin-4-ylidene)-propionic acid ethyl ester 
• 67917-89-9 5-(2-oxo-2-phenyl-ethylidene)-imidazolidine-2,4-dione 
• 66759-18-0 (E)-5-(2-methylpropylene)hydantoin 
• 66759-18-0 (Z)-5-(2-methylpropylene)hydantoin 
• 55666-11-0 (Z)-5-(2-methylpropylidene)imidazolidine-2,4-dione 
• 1343488-97-0 C₇H₁₀N₂O₂ 

Relevant articles and documents

Identification of the hydantoin alkaloids parazoanthines as novel CXCR4 antagonists by computational and in vitro functional characterization

CXCR4 chemokine receptor represents an attractive pharmacological target due to its key role in cancer metastasis and inflammatory diseases. Starting from our previously-developed pharmacophoric model, we applied a combined computational and experimental approach that led to the identification of the hydantoin alkaloids parazoanthines, isolated from the Mediterranean Sea anemone Parazoanthus axinellae, as novel CXCR4 antagonists. Parazoanthine analogues were then synthesized to evaluate the contribution of functional groups to the overall activity. Within the panel of synthesized natural and non-natural parazoanthines, parazoanthine-B was identified as the most potent CXCR4 antagonist with an IC50 value of 9.3 nM, even though all the investigated compounds were able to antagonize in vitro the down-stream effects of CXC12, albeit with variable potency and efficacy. The results of our study strongly support this class of small molecules as potent CXCR4 antagonists in tumoral pathologies characterized by an overexpression of this receptor. Furthermore, their structure–activity relationships allowed the optimization of our pharmacophoric model, useful for large-scale in silico screening.

Synthesis and reactivity of 5-methylenehydantoins

5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.

The use of Lewis acids in the synthesis of 5-arylhydantoins

Different Lewis acids are able to promote the Friedel-Crafts reaction between 5-bromohydantoin and aromatic compounds. In the case of phenol, mixtures of ortho and para isomers are always obtained, with Mg(ClO4) 2 leading to the best selectivity. However, the best overall yield of 5-(hydroxyphenyl)hydantoin is obtained with YbCl3. This method can be extended to other aromatic systems such as anisole and thiophene. These reactions give similar yields but proceed with total selectivity to 5-(4-methoxyphenyl)hydantoin and 5-(2-thiophenyl)hydantoin, respectively. The cationic exchange of MgII and YbIII on anionic solid supports allows the preparation of very efficient heterogeneous catalysts for this reaction (productivity up to 600 mol of hydantoin per mole of Mg). These catalysts have practical advantages in that they can be recycled and reused.