174899-81-1

Basic information

• Product Name: 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide
• Synonyms: 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide;[C1MIm]NTf2;1-Methyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide;1-Methyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide;[MMIm] NTf2;1,3-Dimethylimidazolium Bis(trifluoromethanesulfonyl)imide
• CAS NO: 174899-81-1
• Molecular Formula: C7H9F6N3O4S2
• Molecular Weight: 377.2844792
• Mol File: 174899-81-1.mol

Chemical Properties

• Melting Point: 22°C(lit.)
• Appearance: /
• Density: 1.57 g/cm3(Temp: 30 °C)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide(174899-81-1)
• EPA Substance Registry System: 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide(174899-81-1)

Safety Data

• Hazardous Substances Data: 174899-81-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide is used as a transdermal delivery enhancer for sparingly soluble drugs. Its ability to improve the solubility and permeability of these drugs through the skin allows for more efficient and effective drug delivery, leading to better therapeutic outcomes.
Used in Drug Delivery Systems:
In the field of drug delivery, 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide serves as a promising carrier for various drug molecules. Its unique properties enable the development of novel drug delivery systems that can enhance the bioavailability, stability, and targeted delivery of drugs, ultimately improving their therapeutic effects.

Conductivity

9.36 mS/cm (30 °C)

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 90076-65-6 bis(trifluoromethane)sulfonimide lithium 
• 74-88-4 methyl iodide 
• 79917-88-7 1,3-dimethylimidazolium chloride 
• 82113-65-3 bis(trifluoromethanesulfonyl)amide 
• 4333-62-4 1,3-dimethylimidazolim iodide 
• 97345-90-9 1,3-dimethylimidazolium sulfate monomethyl ester 
• 342789-81-5 1-n-butyl-3-methylimidazolium methanesulfonate 
• 537031-78-0 N-methyl bis[(trifluoromethyl)sulfonyl]imide 

Relevant articles and documents

Structural properties of 1-alkyl-3-methylimidazolium bis{(trifluoromethyl) sulfonyl}amide ionic liquids: X-ray diffraction data and molecular dynamics simulations

X-ray diffraction data for 1-alkyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}amides are reported as a function of the length of the alkyl chain on the imidazolium ring. The measured diffraction patterns have been compared with the theoretical patterns calculated (from the geometries obtained) with molecular dynamics simulations. This provides a detailed description (at the atomistic level) of the morphology in the liquid state of these salts, highlighting the role played by the alkyl chain length. An analysis of the behavior of the hydrogen bonds that are formed between the imidazolium acidic protons and the anion is presented.

Crystal structure of 1,3-dimethylimidazolium bis(fluorosulfonyl)amide: Unexpectedly high melting point arising from polydentate hydrogen bonding

1,3-Dimethylimidazolium bis(fluorosulfonyl)amide, [C1mim]FSA, is an ionic liquid with a lower viscosity than the bis(trifluoromethanesulfonyl) amide salt, [C1mim]NTf2, but with a higher melting point. The single-crystal X-ray structure analysis reveals that this is because the [C1mim]FSA crystal has low coordination ion number and three types of highly symmetric polydentate CH.O hydrogen bonds.

Direct methylation and trifluoroethylation of imidazole and pyridine derivatives

Direct methylation or trifluoroethylation of imidazole and pyridine derivatives using N-methyl bis((perfluoroalkyl)sul-fonyl)imides or trifluoroethyl phenyliodonium bis((trifluoromethyl)sulfonyl)imide affords high yields of the corresponding salts. This methodology provides a simple route to a variety of room temperature ionic liquids (RTILs).

Phase behavior and crystalline phases of ionic liquid-lithium salt mixtures with 1-alkyl-3-methylimidazolium salts

The thermal phase behavior of 1-alkyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide (IM10 RTFSI where R = 1, 2, or 4 for methyl, ethyl or butyl, respectively) ionic liquid binary mixtures with LiTFSI have been investigated as models for electrolytes for lithium batteries. Diverse phase behavior is found with significant variations noted from similar mixtures in which the imidazolium cations are replaced with N-alkyl-N- methylpyrrolidinium cations. The crystal structure for a (1-x) IM 101TFSI-(x) LiTFSI (x = 0.50) (or 1/1 IM101TFSI/LiTFSI) phase is reported to further clarify the molecular level interactions occurring in these binary salt mixtures.

Preparation method of dialkylimidazole bis(trifluoromethylsulfonyl)imide salt

The invention discloses a preparation method of a dialkylimidazole bis(trifluoromethylsulfonyl)imide salt. The method comprises the following steps: 1, reacting alkylimidazole with sulfate in an organic solvent, and layering the obtained solution to obtain a crude dialkylimidazole sulfate product; 2, washing the crude dialkylimidazole sulfate product, carrying out reduced pressure distillation, and drying the obtained product to obtain dialkylimidazole sulfate; 3, reacting the dialkylimidazole sulfate with a bis(trifluoromethylsulfonyl)imide metal salt, and layering the obtained solution to obtain a crude dialkylimidazole bis(trifluoromethylsulfonyl)imide salt product; and 4, washing the crude dialkylimidazole bis(trifluoromethylsulfonyl)imide salt product, carrying out reduced pressure distillation, and drying the obtained product to obtain the target product dialkylimidazole bis(trifluoromethylsulfonyl)imide salt. The method has the advantages of mild reaction conditions, simple operation steps, realization of high yield, high purity and low halogen ion content of the prepared product, and suitableness for promotion and application.

The impact of sulfur functionalisation on nitrogen-based ionic liquid cations

It has been demonstrated that bonding and interactions within ionic liquids (ILs) can be elegantly tuned by manipulation of structure and the introduction of functional groups. Here we use XPS to investigate the impact of sulfur containing substituents on the electronic structure of a series of N-based cations, all with a common anion, [NTf2]-. The experiments reveal complexity and perturbation of delocalised systems which cannot be easily interpreted by NMR and XPS alone, DFT provides critical insight into bonding and underpins the assignment of spectra and development of deconstruction models for each system studied.

Hydrogen bond in imidazolium based protic and aprotic ionic liquids

Liquid structure of bis-(trifluoromethanesulfonyl)amide TFSA- based protic and aprotic ionic liquids composed of imidazolium [h2Im+], N-methylimidazolium [C1hIm+] and N,N'-dimethylimidazolium [C1mIm+] were investigated by high-energy total scattering (HETS) experiments. The nearest neighboring cation-anon orientation variations by the N-methyl groups substitution to proton were suggested based on the peaks at around 6 and 9 ? in the differential radial distribution functions as the form of r2{GX-ray(r) - 1} for these ionic liquids. It was supposed that the NH · · · O hydrogen bond causes the cation-anion orientation variations. To obtain further insight into the hydrogen bond in the PIL, MD simulations performed and agreed well with the experiments. According to spatial distribution functions (SDF) for the three ionic liquids, the O atom of TFSA- prefers the NH hydrogen of the imidazolium that has the most positive partial atomic charge in the cation, while the F atom locates right above and right below the imidazolium ring plane. In addition, the NH · · · O hydrogen bond has short bond lengths and linear bond angles, while the C2H · ·O interaction is long and bent. The NH · · · O hydrogen bond in the PIL was discussed based on structural aspect accompanied by a thermodynamic viewpoint.

Method of preparation of halogen-free ionic liquids and ionic liquids prepared in this manner

The reaction of N-alkylimidazol with alkyl sulfonates, at room temperature, favors the production of 1,3-dialkylimidazolium alkane-sulfonates as crystalline solids at high yields. The alkane-sulfonate anions may be easily substituted by a series of other anions [BF4, PF6, PF3(CF2CF3)3, CF3SO3 and (CF3SO2)2N] through simple anion, salt, or acid reactions in water at room temperature. The extraction with dichloromethane, filtration, and evaporation of the solvent, allows the production of the desired ionic liquids at a yield of 80-95%. The purity of these ionic liquids (in some cases >99.4%) is performed using the intensity of 13C satellite signals from the magnetic resonance spectrums of the N-methyl imidazolium group as an internal standard.

An acidity scale of 1,3-dialkylimidazolium salts in dimethyl sulfoxide solution

(Chemical Equation Presented) Equilibrium acidities of 16 1,3-dialkylimidazolium-type ionic liquid (IL) molecules (1-16) were systematically measured by the overlapping indicator method at 25°C in dimethyl sulfoxide (DMSO) solution. The pKa values were observed to range from 23.4 for IL 12 to 19.7 for IL 6 (Tables 1 and 2), responding mainly to structural variations on the cation moiety. Excellent agreement between the spectrophotometrically determined pKa and that derived from NMR titration for 1,3,4,5-tetramethylimidazolium bis(trifluoromethanesulfonyl)imide (12) and the close match of the obtained pK values with the reported data in literature provide credence to the acidity measurements of the present work. The substituent effects at the imidazolium ring and the effects of counterions on the acidities of ionic liquids are discussed.