10040-87-6

Basic information

• Product Name: 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione
• CAS NO: 10040-87-6
• Molecular Formula: C₁₂H₁₃N₃O₂
• Molecular Weight: 231.2505
• Mol File: 10040-87-6.mol
• Article Data: 12

Chemical Properties

• Density: 1.287g/cm³
• Refractive Index: 1.653
• CAS DataBase Reference: 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione(10040-87-6)
• EPA Substance Registry System: 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione(10040-87-6)

Safety Data

• Hazardous Substances Data: 10040-87-6(Hazardous Substances Data)

Usage

Description

5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione, also known as Meldrum's acid derivative, is a chemical compound that features a benzylidene-2,4-dione moiety attached to an imidazolidine ring. This versatile building block in organic chemistry is known for its ability to participate in various reactions, including nucleophilic addition, cycloaddition, and condensation. The presence of a dimethylamino group on the benzylidene ring enhances its utility as a ligand in organometallic chemistry and catalysis, making it a valuable compound in the fields of organic and medicinal chemistry.

Uses

Used in Pharmaceutical Synthesis:
5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to form complex molecular structures that can exhibit therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione serves as a crucial component in the development of new compounds designed to protect crops and enhance agricultural productivity.
Used in Organic Chemistry Research:
As a versatile building block, 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione is used in organic chemistry research to explore novel reactions and mechanisms, contributing to the advancement of chemical knowledge and the discovery of new synthetic pathways.
Used as a Ligand in Organometallic Chemistry:
The dimethylamino group in 5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione makes it an effective ligand for use in organometallic chemistry, where it can influence the properties and reactivity of metal complexes.
Used in Catalysis:
5-[4-(dimethylamino)benzylidene]imidazolidine-2,4-dione's structural features make it suitable for use in catalytic processes, where it can facilitate or enhance the rate of chemical reactions, improving the efficiency of industrial and laboratory processes.

Upstream product

• 461-72-3 2,4-imidazolidinedione 
• 120-21-8 4-Diethylaminobenzaldehyde 
• 41250-31-1 5-(4-dimethylamino-benz-(Z)-ylidene)-2-thioxo-imidazolidin-4-one 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 

Downstream Products

• 924863-99-0 2-[5-(4-dimethylamino-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 1416719-85-1 C₁₇H₂₁N₃O₃ 
• 1388167-51-8 (Z)-5-(4-(dimethylamino)benzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1-yl)-2-hydroxypropyl)imidazolidine-2,4-dione 
• 1388167-46-1 (Z)-5-(4-(dimethylamino)benzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 1388167-22-3 C₁₅H₁₇N₃O₃ 
• 58841-92-2 5-(4-dimethylaminobenzyl)imidazolidine-2,4-dione 

Relevant articles and documents

Synthesis and antidepressant activity of 5-(4-dimethylaminobenzyl)imidazolidine-2,4-dione

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Search for new tools to combat Gram-negative resistant bacteria among amine derivatives of 5-arylidenehydantoin

A series of amine-alkyl derivatives of 5-arylidenehydantoin 3-21 was evaluated for their ability to improve antibiotic effectiveness in two strains of Gram-negative Enterobacter aerogenes: the reference strain (ATCC-13048) and the chloramphenicol-resistan

Synthesis and SAR-study for novel arylpiperazine derivatives of 5-arylidenehydantoin with α1-adrenoceptor antagonistic properties

The study is focused on a series of 5-arylidenehydantoin derivatives with a phenylpiperazine-hydroxypropyl fragment at N3 of the hydantoin ring. The compounds were assessed on their affinity for α1-adrenoceptors and evaluated in functional bioassays for their antagonistic properties. Crystal structures of (Z)-5-(4-chlorobenzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1- yl)-2-hydroxypropyl)imidazolidine-2,4-dione (7) and hydrochloride of (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl) propyl)imidazolidine-2,4-dione (10a) were solved using the X-ray diffraction method. Classical molecular mechanics (MMFFs force field, MCMM, MacroModel) were used to predict 3D structure of compounds 5a-18a using a crystal structure of 7. SAR analysis was performed on the basis of Barbaro's pharmacophore model and structural properties of previously investigated α1- adrenoceptor antagonists possessing a hydantoin fragment. Most of the compounds exhibited significant affinities for α1-ARs in nanomolar range (40-290 nM). The highest activities (Ki 1-affinities as follows: 3,4-di CH3O>2,4-di CH3O>4-Cl>2,3-di CH 3O>H>4-N(CH3)2.