80-73-9

Basic information

• Product Name: 1,3-Dimethyl-2-imidazolidinone
• Synonyms: DMEU;DMI;DIMETHYLETHYLENE UREA;1,3-dimethyl-2-imidazodinone;1,3-dimethyl-2-imidazolidinon;1,3-Dimethyl-2-imidazolidone;1,3-Dimethylethyleneurea;2-Imidazolidinone, 1,3-dimethyl-
• CAS NO: 80-73-9
• Molecular Formula: C₅H₁₀N₂O
• Molecular Weight: 114.15
• EINECS: 201-304-8
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Imidazolines/Imidazolidines;Imidazol&Benzimidazole;Heterocyclic Compounds
• Mol File: 80-73-9.mol
• Article Data: 57

Chemical Properties

• Melting Point: 8.2 °C
• Boiling Point: 224-226 °C(lit.)
• Flash Point: 220 °F
• Appearance: Clear/Liquid
• Density: 1.056 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.114mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Storage Temp.: Store at +5°C to +30°C.
• Solubility: toluene: soluble(lit.)
• PKA: -0.65±0.20(Predicted)
• Explosive Limit: 1.3-8.4%(V)
• Water Solubility: freely soluble
• Sensitive: Hygroscopic
• Merck: 14,3249
• BRN: 108808
• CAS DataBase Reference: 1,3-Dimethyl-2-imidazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethyl-2-imidazolidinone(80-73-9)
• EPA Substance Registry System: 1,3-Dimethyl-2-imidazolidinone(80-73-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 21/22-38-41-36/38-62-22
• Safety Statements: 26-36-36/37/39-36/37
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: NJ0660000
• F: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 80-73-9(Hazardous Substances Data)

Usage

Description

DMI, a high purity aprotic solvent, is composed of nitrogen containing five membered ring compound and widely recognized as an epoch making solvent. It is a colorless, transparent, high polar solvent with high thermal and chemical stability and non-corrosiveness. The material has a high boiling point of 222° C, a high flash point of 120° C (open method) / 95° C (close method), and a low melting point of 7.5° C.

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 
• 96-45-7 N,N'-ethylenethiourea 
• 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) 

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 
• 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 
• 374556-30-6 N-[3-(4,5-dimethyl-1H-imidazol-1-yl)phenyl]-7-(trifluoromethyl)-4-quinazolinamine 

Relevant articles and documents

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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.

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.

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.

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.