1334703-07-9

Basic information

• Product Name: 1,3-bis(2-ethoxy-2-oxoethyl)-1H-imidazol-3-ium chloride
• CAS NO: 1334703-07-9
• Molecular Weight: 276.72
• Mol File: 1334703-07-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3-bis(2-ethoxy-2-oxoethyl)-1H-imidazol-3-ium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-bis(2-ethoxy-2-oxoethyl)-1H-imidazol-3-ium chloride(1334703-07-9)
• EPA Substance Registry System: 1,3-bis(2-ethoxy-2-oxoethyl)-1H-imidazol-3-ium chloride(1334703-07-9)

Safety Data

• Hazardous Substances Data: 1334703-07-9(Hazardous Substances Data)

Usage

Derivative of

Imidazole

Common use

Pharmaceutical ingredient

Antimicrobial properties

Yes

Antifungal properties

Yes

Potential application

Treatment of bacterial and fungal infections

Cytotoxic properties

Yes

Additional potential application

Treatment of cancer

Versatility

High, due to its promising pharmacological properties

Upstream product

• 64-17-5 ethanol 
• 117255-11-5 2-(1-(carboxymethyl)-1H-imidazol-3-ium-3-yl)acetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 288-32-4 1H-imidazole 

Relevant articles and documents

N-alkylation of N-trimethylsilylimidazole

The reaction of N-trimethylsilylimidazole with alkyl chloroacetates is studied. This process yields a mixture of N-alkylation and quarternization products in the ratio dependent on the reaction conditions. The reaction mechanism is discussed. 1H NMR data show that high melting point and low solubility of 1-imidazolylacetic acid in organic solvents are evidently caused by the formation of strong intermolecular hydrogen bonds, whereas in water zwitterionic structures with the protonation of both nitrogen atoms are formed.

Synthesis and biological activity of ester- and amide-functionalized imidazolium salts and related water-soluble coinage metal N-heterocyclic carbene complexes

N-Heterocyclic carbene (NHC) ligand precursors, namely, HImACl [1,3-bis(2-ethoxy-2-oxoethyl)-1H-imidazol-3-ium chloride] and HImBCl {1,3-bis[2-(diethylamino)-2-oxoethyl]-1H-imidazol-3-ium chloride}, functionalized with hydrophilic groups on the imidazole rings have been synthesized and were used in the synthesis of corresponding carbene complexes of silver(I) and copper(I), {[ImA]AgCl}, {[ImA]CuCl}, and {[ImB]2Ag}Cl. Related AuINHC complexes {[ImA]AuCl} and {[ImB]AuCl} have been obtained by transmetalation using the silver carbene precursor. These compounds were characterized by several spectroscopic techniques including NMR and mass spectroscopy. HImBCl and the gold(I) complexes {[ImA]AuCl} and {[ImB]AuCl} were also characterized by X-ray crystallography. The cytotoxic properties of the NHC complexes have been assessed in various human cancer cell lines, including cisplatin-sensitive and -resistant cells. The silver(I) complex {[ImB]2Ag}Cl was found to be the most active, with IC50 values about 2-fold lower than those achieved with cisplatin in C13*-resistant cells. Growth-inhibitory effects evaluated in human nontransformed cells revealed a preferential cytotoxicity of {[Im B]2Ag}Cl versus neoplastic cells. Gold(I) and silver(I) carbene complexes were also evaluated for their ability to in vitro inhibit the enzyme thioredoxin reductase (TrxR). The results of this investigation showing that TrxR appeared markedly inhibited by both gold(I) and silver(I) derivatives at nanomolar concentrations clearly point out this selenoenzyme as a protein target for silver(I) in addition to gold(I) complexes.

Amino acid-derived N-heterocyclic carbene palladium complexes for aqueous phase Suzuki-Miyaura couplings

In this work, three ligands produced from amino acids were synthesized and used to produce five bis- and PEPPSI-type palladium-NHC complexes using a novel synthesis route from sustainable starting materials. Three of these complexes were used as precatalysts in the aqueous-phase Suzuki-Miyaura coupling of various substrates displaying high activity. TEM and mercury poisoning experiments provide evidence for Pd-nanoparticle formation stabilized in water.