23996-53-4

Basic information

• Product Name: N-(2-CYANOETHYL)-IMIDAZOLE
• Synonyms: N-(2-CYANOETHYL)-IMIDAZOLE;3-(1H-IMIDAZOL-1-YL)PROPANENITRILE;AKOS B018548;ART-CHEM-BB B018548;1H-Imidazole-1-propanenitrile(9CI)
• CAS NO: 23996-53-4
• Molecular Formula: C₆H₇N₃
• Molecular Weight: 121.14
• EINECS: 1533716-785-6
• Product Categories: AMINETERTIARY
• Mol File: 23996-53-4.mol

Chemical Properties

• Melting Point: 35-36 °C
• Boiling Point: 145 °C
• Flash Point: 164.9 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 4.83E-05mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• PKA: 6.55±0.10(Predicted)
• CAS DataBase Reference: N-(2-CYANOETHYL)-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-CYANOETHYL)-IMIDAZOLE(23996-53-4)
• EPA Substance Registry System: N-(2-CYANOETHYL)-IMIDAZOLE(23996-53-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 23996-53-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
N-(2-Cyanoethyl)-Imidazole is used as a catalyst in chemical synthesis processes, leveraging its strong nucleophilic properties to facilitate reactions and improve the efficiency of the synthesis.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-(2-Cyanoethyl)-Imidazole serves as a key intermediate or catalyst in the production of various drugs, contributing to the development of new medications and therapeutic agents.
Used in Industrial Applications:
N-(2-Cyanoethyl)-Imidazole is employed in a range of industrial applications, where its unique chemical properties are harnessed to enhance the performance of different products and processes. Its versatility makes it a valuable component in various sectors, including materials science and chemical engineering.

InChI:InChI=1/C6H7N3/c7-2-1-4-9-5-3-8-6-9/h3,5-6H,1,4H2

Upstream product

• 288-32-4 1H-imidazole 
• 542-76-7 3-Chloropropionitrile 
• 107-13-1 acrylonitrile 

Downstream Products

• 1318779-41-7 C₁₈H₁₆Cl₂N₃O₅⁽¹⁺⁾*Cl^(1-) 
• 1318779-42-8 C₂₀H₂₀Cl₂N₃O₅⁽¹⁺⁾*Cl^(1-) 
• 1318779-37-1 1-{2-[3,4-bis(4-chlorobutyryloxy)phenyl]-2-oxoethyl}-3-(2-cyanoethyl)-3H-imidazol-1-ium chloride 
• 1602589-74-1 C₁₄H₂₄N₃⁽¹⁺⁾*C₆H₅O₃S^(1-) 
• 65991-91-5 2-(1H-imidazol-1-yl)acetamide 
• 1384463-33-5 Br^(1-)*C₂₂H₁₈N₃⁽¹⁺⁾ 
• 1384463-35-7 Br^(1-)*C₂₂H₁₆Cl₂N₃⁽¹⁺⁾ 
• 1384463-36-8 Br^(1-)*C₂₄H₂₂N₃O₂⁽¹⁺⁾ 
• 1282511-48-1 C₇H₅O₅S^(1-)*C₁₂H₂₀N₃⁽¹⁺⁾ 
• 1282511-47-0 1-hexyl-3-propanenitrileimidazolium benzenesulfonate 
• 1310687-00-3 1-butyl-3-propanenitrile imidazolium benzenesulfonate 
• 93668-04-3 2-Allylamino-5-chloro-N-(3-imidazol-1-yl-propyl)-benzamide 
• 93669-31-9 N-(3-(1H-imidazol-1-yl)propyl)-4-(trifluoromethyl)benzamide 
• 93669-36-4 N-(3-Imidazol-1-yl-propyl)-3-trifluoromethyl-benzamide 

Relevant articles and documents

Structures and single crystal to single crystal transformations of cadmium frameworks using a flexible tripodal ligand

A highly flexible tris-imidazole ligand N(CH2-m-C6H4-CH2-imidazole)3 (L) constructed using a tris(xylyl) backbone was synthesized. Its reactions with three cadmium(ii) salts gave various Cd(ii) coordination polymers, namely [CdL2](ClO4)2 (1), [CdLCl2] (2), and [CdL(OAc)2] (3). X-ray studies revealed that 1 crystallized in the trigonal space group R3 with high symmetry, while 2 and 3 crystallized in lower symmetrical space groups due to Cd-anion coordination. The flexibility of ligand L was evidenced in these structures, showing different conformations of L upon coordination and crystallization. In addition, complex [CdL2]Cl2 (4) was obtained by the anion exchange of 1 with sodium chloride via a single crystal to single crystal transformation. Similar to 1, complex 4 also crystallized in the trigonal space group R3 with a = 13.0945(3), b = 37.4353(10), and V = 5559.2(2). Importantly, this single crystal to single crystal transformation is crucial to afford this Cd(ii) coordination polymer with unbound Cl- anions, as the direct reaction of L and CdCl2 gives complex 2 with Cd-bound Cl-. This work shows the importance of flexible ligands in constructing various coordination polymer structures through the regulation of anions.

Study of preparation and thermal stability of cyano-functionalized imidazolium type ionic liquids

Sixteen imidazolium type cyano-functionalized Br?nsted acidic ionic liquids with HSO4- and H2PO4 - anion were prepared adopting twostep method and were characterized by FT-IR, 1H and 13C NMR. The onse

Physicochemical and thermodynamic properties of imidazolium ionic liquids with nitrile and ether dual functional groups

Synthesis of new dual functionalized imidazolium ionic liquids (ILs) containing nitrile functionality and ether group were synthesized and characterized. Bis(trifluoromethylsulfonyl)imide, trifluoroacetate and dicyanamide were used as the anion. The combination of two functional groups on an imidazolium cation was mainly developed to assess their potential in desulfurization of fuel oil. Although ILs based on this individual functional group has been reported to improve the desulfurization efficiency, no effort has been made to combine nitrile and ether functional groups on the same cation to enhance the desulphurization potential. In this report, we tailored both nitrile and ether functionality on imidazolium cation and studied their physicochemical properties in details. NMR (1H and 13C) spectroscopy and elemental analysis were used to characterize the synthesized ILs. Physical properties and optical properties of the ILs were investigated in a wide temperature range. The synthesized ILs showed good thermal stability. COSMO-RS was effectively utilized to discuss the σ surface, σ potential and σ profile of the synthesized ILs.

Effect of Structural Variations on the Thermophysical Properties of Protic Ionic Liquids: Insights from Experimental and Computational Studies

In this work, new protic ionic liquids (PILs) based on 1-methylimidazolium/1-propanenitrileimidazolium cations with hydrogen sulfate, methanesulfonate, trifluoromethanesulfonate, para-toluenesulfonate, trifluoroacetate, and acetate anions were synthesized. The structures and purity of the products were confirmed by using 1H and 13C NMR and CHNS elemental analysis. The effect of structural variations on the thermophysical properties, namely, refractive index, density, and viscosity, was evaluated in a wide temperature range. The viscosity and density values were measured within the temperature range of 293.15-373.15 K. The density values were used further to calculate more properties like thermal expansion coefficient, molecular volume, standard entropy, and the lattice energy. Moreover, the experimental values of viscosity were used for the calculation of activation energy. Refractive indices were measured within the temperature range of 293.15-323.15 K, and these values were also used in the calculation of electronic polarizability. Acid numbers of the prepared PILs were measured and correlated with their structure moiety. In addition, the density functional theory (DFT) calculations were performed to get a deeper insight into the effect of structural variations of the ion pairs on their physical properties.

Thermophysical properties of a new dicationic ionic liquid

A new functionalized dicationic ionic liquid was synthesized with the final aim of studying its application in the extraction of metal ions in the mineral industry. In light of this application, the density, refractive index, and dynamic viscosities have been determined and correlated as a function of temperature. Density data were used to calculate the volumetric properties of the ionic liquid. Several empirical equations were used to evaluate the correlation between the density and refractive indices. The results show that the modified Eykman equation has the best fit. In addition, thermal behavior was measured by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), and a high thermal stability and a wide liquid phase range were determined.

Thermophysical properties of dual functionalized imidazolium-based ionic liquids

In this work, some new dual functionalized imidazolium-based ionic liquids 3-(3-butyl-1H-imidazol-3-ium-1-yl)propanenitrile chloride [C2CNBim] Cl, 3-(3-allyl-1H-imidazol-3-ium-1-yl)propanenitrile chloride [C 2CNAim]Cl, 3-[3-(2-hydrox

Thermophysical properties of 1-propyronitrile-3-alkylimidazolium bromide ionic liquids at temperatures from (293.15 to 353.15) K

In the present work, a series of 1-propyronitrile-3-alkylimidazolium bromide ionic liquids ([C2CN Cnim]Br, where n = 4, 6, 8, and 10) were synthesized and characterized using Fourier transform infrared spectroscopy (FTIR), NMR, and elemental analysis. Physical properties such as density, viscosity, and refractive index are measured and reported for a temperature range of (293.15 to 353.15) K and at atmospheric pressure. The influence of the alkyl chain on these properties is discussed. The present synthesized ionic liquids show a weak temperature dependency on the thermal expansion coefficient.

A Novel zwitterionic imidazolium-based ionic liquid surfactant: 1-carboxymethyl-3-dodecylimidazolium inner salt

A novel zwitterionic imidazolium-based ionic liquid (IL) surfactant, 1-carboxymethyl-3-dodecylimidazolium inner salt, was synthesized. The molecule structure was confirmed by means of electrospray ionization mass spectrometry, 1H nuclear magnetic resonance and elemental analysis. The isoelectric point (pI) is 3.8 ± 0.1 at 35 ± 0.1 °C. The other important physicochemical parameters such as the critical micelle concentration (CMC), the surface tension at CMC (γCMC), the adsorption efficiency (pC 20), the surface pressure at CMC (ΠCMC), the maximum surface excess (Γm), the minimum molecular cross-sectional area (A min), the value of CMC/C 20 and the average number of aggregation (N m) were determined by surface tension and steady-state fluorescence probe methods, respectively. AOCS 2011.

Synthesis and self-aggregation of a hydroxyl-functionalized imidazolium-based ionic liquid surfactant in aqueous solution

This paper deals with the synthesis and self-aggregation of a hydroxyl-functionalized imidazoliumbased ionic liquid (IL) surfactant, namely 1-hydroxyethyl-3-dodecylimidazolium chloride ([C2OHC 12im]Cl). The molecular structure was confirmed by means of electrospray ionization mass spectrometry (ESI-MS), 1H nuclear magnetic resonance (1H NMR) and elemental analysis. Many important physicochemical parameters, such as the critical micelle concentration (CMC), the surface tension at CMC (γCMC), the adsorption efficiency (pC20), the surface pressure at CMC (ΠCMC), the maximum surface excess (Γm), the minimum molecular cross-sectional area (Amin), the value of CMC/C20, the average number of aggregation (Nm) and the micellar microenvironment polarity were determined by surface tension-concentration curves, fluorescence spectra, and electrical conductivity. The phenomena of the second CMC, the concentration dependence of Nm, and the critical average aggregation number (N m,c) of imidazolium-based IL surfactants are reported for the first time in this paper. AOCS 2010.

One-pot solvent-free microwave-assisted aza-Michael addition reaction of acrylonitrile

A novel and highly effective one-pot microwave-assisted aza-Michael addition reaction of acrylonitrile, as Michael acceptor with various primary aliphatic and aromatic amines, as Michael donor has been reported. The reaction was catalyzed by a cost-effective, highly efficient and eco-friendly catalyst, molecular sieve of 4 A0 size, under solvent-free conditions. A detail investigation on reaction controlling parameters like reaction timing and amount of catalyst was studied. The plausible mechanistic pathway has been proposed for the formation of acrylonitrile adducts. The identity of the synthesized products was established by conventional spectroscopic techniques FT-IR, 1H and 13C{1H} NMR, ESI-MS and DLS measurements. DLS result shows hydrodynamic diameter of lower alkyl chain in the range of 200–300 nm and for higher alkyl chain around 1 μm. Sheldon's hot filtration test confirms the significance of the catalyst and their heterogeneity was also confirmed by recycling it for five consecutive cycles without any noticeable change in the yield.