80-73-9

Usage

Chemical Properties

Almost colorless, clear liquid

Uses

Different sources of media describe the Uses of 80-73-9 differently. You can refer to the following data:
1. 1,3-Dimethyl-2-imidazolidinone is used as a high-boiling polar aprotic solvent. It is used as a substitute solvent for toxic hexamethylphosphoramide. It finds application in detergents, dyestuffs, electronic materials and in the manufacture of polymers. It is involved in the preparation of 1,2-bis(trimethylsilyl)benzene. Further, it is utilized as a solvent during alfa-regioselective prenylation of imines. In addition to this, it constitutes the mobile phase during size-exclusion chromatographic analysis of cellulose.
2. DMI can be used in a variety of applications including detergents, dyestuffs, electronic materials and in the manufacture of polymers. Its versatility can be attributed to it. Of particular note are its excellent solubility for inorganic and organic compounds and high dielectric constant and solvation effect.
3. 1,3-Dimethyl-2-imidazolidinone may be used:As substitute solvent for hexamethylphosphoric triamide (HMPA) in the synthesis of 1,2-bis(trimethylsilyl)benzene. As solvent during the α-regioselective prenylation of imine.As component of mobile phase for the size-exclusion chromatographic analysis of cellulose.

General Description

1,3-Dimethyl-2-imidazolidinone (DMI) is an imidazolidine derivative. It is reported to act as a promoter by minimizing the formation of dialkylation byproducts and accelerating the rate of monoalkylation of γ-butyrolactone. Conversion of CO2 to form lower alcohols by homogeneous catalytic hydrogenation using DMI as solvent has been investigated.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3

Upstream product

• 2669-72-9 1,3-bis(methoxymethyl)-2-imidazolidinone 
• 110-91-8 morpholine 
• 120-93-4 imidazolidone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 20112-79-2 2-methylthioimidazoline 
• 124-38-9 carbon dioxide 
• 138767-61-0 N,N'-dimethyl<(8-dimethylaminomethyl)naphthyl>phenylsila-2-imidazoline 
• 68696-80-0 1,1'-dimethyl-1,1'dimethylenebisurea 
• 122734-28-5 N-methyl-N-<2-(methylamino)ethyl>carbamic acid 4-methoxyphenyl ester hydrochloride 
• 124-41-4 sodium methylate 
• 555-21-5 4-Nitrophenylacetonitrile 
• 78581-33-6 Bis(1,3-dimethylimidazolinium-2-yl)ether-bis(trifluormethansulfonat) 
• 108-91-8 cyclohexylamine 

Downstream Products

• 426225-93-6 (1R,4S)-4-hydroxycyclopent-2-en-1-essigsaeure-methylester 
• 14103-77-6 1,3-dimethylimidazolidine 
• 13461-16-0 1,3-dimethylimidazolidine-2-thione 
• 486-25-9 9-fluorenone 
• 141-53-7 sodium formate 
• 110-70-3 N,N`-dimethylethylenediamine 
• 101385-69-7 2-chloro-1,3-dimethyl-2-imidazolinium hexafluorophosphate 
• 202282-59-5 1,3-dimethyl-2-(N',N',N,N-tetramethylguanidino)-4,5-dihydro-3H-imidazolium chloride 
• 5349-60-0 1-(4-methoxyphenyl)-1-propanol 
• 374555-71-2 N-[3-(1,2-dimethyl-1H-imidazol-5-yl)phenyl]-5,6-dihydrobenzo[h]quinazolin-4-amine 
• 374556-27-1 N-[3-(1,2-dimethyl-1H-imidazol-5-yl)phenyl]-8-(trifluoromethyl)-4-quinazolinamine 
• 374556-29-3 N-[3-(1,2-dimethyl-1H-imidazol-5-yl)phenyl]-7-(trifluoromethyl)-4-quinazolinamine 
• 374556-61-3 N-[3-(4,5-dimethyl-1H-imidazol-1-yl)phenyl]-9-fluoro-5,6-dihydrobenzo[h]quinazolin-4-amine 
• 374556-28-2 N-[3-(4,5-dimethyl-1H-imidazol-1-yl)phenyl]-8-(trifluoromethyl)-4-quinazolinamine 

Relevant academic research and scientific papers

Reaction of 3,4-Di-t-butylthiophene 1-oxide with 2-methylene-1,3-dimethylimidazolidine: Methylene transfer and [4+4] dimerization

The reaction of 3,4-di-t-butylthiophene 1-oxide (1) with 2-methylene-1,3-dimethylimidazolidine (2) gave 4,4a-di(t-butyl)-1a,4a-dihydro-1H-cyclopropa[b]thiophene and 1,3-dimethyl-2-imidazolidinone through a methylene transfer from 2 to 1, in addition to a [4+4] cyclodimerization product of 1.

A DIPOLE MOMENT STUDY OF N-METHYL AND N,N'-DIMETHYL-IMIDAZOLIDIN-2-ONES, IMIDAZOLIDINE-2-THIONES AND -2-SELENONES

The electric dipole moments in benzene and dioxan of potentially tautomerizable N-methylimidazolidin-2-one, N-methylimidazolidine-2-thione and -2-selenone clearly support the lactam structure for these compounds.The fact that their dipole moments in dioxan are markedly greater than those in benzene is explained by a higher (HN-C=Y) mesomeric moment in the hydrogen-bonded solute...dioxan complexes.Analysis of the dipole moments in benzene of N,N'-dimethylimidazolidin-2-one, N,N'dimethylimidazolidine-2-thione and -2-selenone shows that the mesomeric moment (due to contribution of +N=C-Y- zwitterionic valence structures) gradually increases on going from Y=O to Y=S, and Y=Se.Finally, preferred conformations, from their dipole moments in benzene, are suggested for tetramethylurea and tetramethylthiourea.

Mesoporous silica-catalysed continuous chemical fixation of CO2 with N,N′-dimethylethylenediamine in supercritical CO2: The efficient synthesis of 1,3-dimethyl-2-imidazolidinone

MCM-41- and HMS-type mesoporous silicas were found to be efficient catalysts for the continuous chemical fixation of CO2 into 1,3-dimethyl-2-imidazolidinone with N,N′-dimethylethylenediamine in supercritical CO2. The Royal Society of Chemistry.

Optochemical Control of Bacterial Gene Expression: Novel Photocaged Compounds for Different Promoter Systems

Photocaged compounds are applied for implementing precise, optochemical control of gene expression in bacteria. To broaden the scope of UV-light-responsive inducer molecules, six photocaged carbohydrates were synthesized and photochemically characterized, with the absorption exhibiting a red-shift. Their differing linkage through ether, carbonate, and carbamate bonds revealed that carbonate and carbamate bonds are convenient. Subsequently, those compounds were successfully applied in vivo for controlling gene expression in E. coli via blue light illumination. Furthermore, benzoate-based expression systems were subjected to light control by establishing a novel photocaged salicylic acid derivative. Besides its synthesis and in vitro characterization, we demonstrate the challenging choice of a suitable promoter system for light-controlled gene expression in E. coli. We illustrate various bottlenecks during both photocaged inducer synthesis and in vivo application and possibilities to overcome them. These findings pave the way towards novel caged inducer-dependent systems for wavelength-selective gene expression.

SBA-15 Supported Dendritic ILs as a Green Catalysts for Synthesis of 2-Imidazolidinone from Ethylenediamine and Carbon Dioxide

In this work, a simple and facile approach is conducted for preparing many new SBA-15 supported dendritic imidazolium ILs heterogeneous catalysts SBA-15/IL(1–3) having high ionic density from SBA-15. SBA-15/IL(3) as a green heterogeneous catalyst can be used for synthesis of 2-imidazolidinone from ethylenediamine and carbon dioxide and considering solvent-free condition. SBA-15/IL(3) showed to have the highest catalytic activity besides a positive dendritic influence on the yields of the synthesis of 2-imidazolidinone in the presence of CO2 is seen because of existing the high-density peripheral zwitterionic ionic liquid functional groups on the biobased SBA-15/IL(3) catalyst surfaces. Graphical Abstract: [Figure not available: see fulltext.]

Reaction of Nitroxyl (HNO) with Hydrogen Sulfide and Hydropersulfides

Nitroxyl (HNO) has gained a considerable amount of attention because of its promising pharmacological effects. The biochemical mechanisms of HNO activity are associated with the modification of regulatory thiol proteins. Recently, several studies have suggested that hydropersulfides (RSSH), presumed signaling products of hydrogen sulfide (H2S)-mediated thiol (RSH) modification, are additional potential targets of HNO. However, the interaction of HNO with reactive sulfur species beyond thiols remains relatively unexplored. Herein, we present characterization of HNO reactivity with H2S and RSSH. The reaction of H2S with HNO leads to the formation of hydrogen polysulfides and sulfur (S8), suggesting a potential role in sulfane sulfur homeostasis. Furthermore, we show that hydropersulfides are more efficient traps for HNO than their thiol counterparts. The reaction of HNO with RSSH at varied stoichiometries has been examined with the observed production of various dialkylpolysulfides (RSSnSR) and other nitrogen-containing dialkylpolysulfide species (RSS-NH-SnR). We do not observe evidence of sulfenylsulfinamide (RS-S(O)-NH2) formation, a pathway expected by analogy with the known reactivity of HNO with thiol.

Alkylamine-Substituted Perthiocarbamates: Dual Precursors to Hydropersulfide and Carbonyl Sulfide with Cardioprotective Actions

The recent discovery of hydropersulfides (RSSH) in mammalian systems suggests their potential roles in cell signaling. However, the exploration of RSSH biological significance is challenging due to their instability under physiological conditions. Herein, we report the preparation, RSSH-releasing properties, and cytoprotective nature of alkylamine-substituted perthiocarbamates. Triggered by a base-sensitive, self-immolative moiety, these precursors show efficient RSSH release and also demonstrate the ability to generate carbonyl sulfide (COS) in the presence of thiols. Using this dually reactive alkylamine-substituted perthiocarbamate platform, the generation of both RSSH and COS is tunable with respect to half-life, pH, and availability of thiols. Importantly, these precursors exhibit cytoprotective effects against hydrogen peroxide-mediated toxicity in H9c2 cells and cardioprotective effects against myocardial ischemic/reperfusion injury, indicating their potential application as new RSSH- and/or COS-releasing therapeutics.

A near-infrared fluorescence probe for imaging of pantetheinase in cells and mice: In vivo

Pantetheinase is an amidohydrolase that cleaves pantetheine into pantothenic acid and cysteamine. Functional studies have found that ubiquitous expression of this enzyme is associated with many inflammatory diseases. However, the lack of near-infrared fluorescence probes limits the better understanding of the functions of the enzyme. In this work, we have developed a new near-infrared fluorescence probe, CYLP, for bioimaging of pantetheinase by using pantothenic acid with a self-immolative linker as a recognition group. The probe produces a sensitive fluorescence off-on response at 710 nm to pantetheinase with a detection limit of 0.02 ng mL-1 and can be used to image the intraperitoneal pantetheinase activity in mice in vivo. Moreover, with the probe we have observed that pantetheinase is significantly increased in the tissues of mouse inflammatory models as well as in the intestines of mice with inflammatory bowel disease. Therefore, CYLP may provide a convenient and intuitive tool for studying the role of pantetheinase in diseases.

Fast Cyclization of a Proline-Derived Self-Immolative Spacer Improves the Efficacy of Carbamate Prodrugs

Self-immolative (SI) spacers are sophisticated chemical constructs designed for molecular delivery or material degradation. We describe herein a (S)-2-(aminomethyl)pyrrolidine SI spacer that is able to release different types of anticancer drugs (possessing either a phenolic or secondary and tertiary hydroxyl groups) through a fast cyclization mechanism involving carbamate cleavage. The high efficiency of drug release obtained with this spacer was found to be beneficial for the in vitro cytotoxic activity of protease-sensitive prodrugs, compared with a commonly used spacer of the same class. These findings expand the repertoire of degradation machineries and are instrumental for the future development of highly efficient delivery platforms.

THIOL COMPOUND PRODUCTION METHOD AND NOVEL THIATING AGENT

PROBLEM TO BE SOLVED: To provide: a thiol compound production method which allows selective production of a thiol compound of interest, inhibits production of by-products ending up wastes, is excellent in production efficiency, and can reduce production costs; and a novel thiating agent used for the method. SOLUTION: The thiol compound production method comprises: a step 1 of preparing a thiuronium salt by reacting at least one compound represented by the general formula (1) defined by R-(X)m with a thiating agent comprising at least one compound selected from compounds represented by the general formula (2) in the figure; and a step 2 of hydrolyzing the thiuronium salt to prepare a compound represented by the general formula (3) defined by R-(SH)m. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT