616-47-7

Basic information

• Product Name: N-Methylimidazole
• Synonyms: Imidazole, 1-methyl-;N-methylimidazole (1-methylimidazole);N-methyl midazole;N-methyl glyoxaline;CAP B (1-METHYLIMIDAZOLE 12% IN ACETONIT;1-Methylimidazole, >=99%, purified by redistillation;CAP B (1-METHYLIMIDAZOLE 10% IN THF)*;CAP B (1-METHYLIMIDAZOLE 10% IN
• CAS NO: 616-47-7
• Molecular Formula: C₄H₆N₂
• Molecular Weight: 82.1
• EINECS: 210-484-7
• Product Categories: Imidazoles;Heterocyclic Compounds;Heterocycles;Metabolites & Impurities;Building Blocks;Heterocyclic Building Blocks;Carbonate dehydrataseEnzyme Inhibitors by Enzyme;Histidinol dehydrogenaseBuilding Blocks;A to;D to;Enzyme Inhibitors by Enzyme;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;C3 to C8;Carbonate dehydratase;Histidinol dehydrogenase;A to C;and Substrates;Biochemicals and Reagents;D to K;Enzyme Inhibitors;Enzyme Inhibitors by Enzyme;Enzymes;Inhibitors;Heterocycles, Metabolites & Impurities
• Mol File: 616-47-7.mol

Chemical Properties

• Melting Point: −60 °C(lit.)
• Boiling Point: 198 °C(lit.)
• Flash Point: 198 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.03 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.495(lit.)
• Storage Temp.: Store at RT.
• PKA: 6.95(at 25℃)
• Explosive Limit: 2.7-15.7%(V)
• Water Solubility: Miscible with water.
• Sensitive: Hygroscopic
• Stability: Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, aci
• BRN: 105197
• CAS DataBase Reference: N-Methylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylimidazole(616-47-7)
• EPA Substance Registry System: N-Methylimidazole(616-47-7)

Safety Data

• Hazard Codes: C,Xn,F,T
• Statements: 21/22-34-19-11-20/21/22-52/53-24-22-40-37-21
• Safety Statements: 26-36-45-1/2-36/37/39-16-33-29-61
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 1
• RTECS: NI7000000
• F: 3-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 616-47-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Pesticide Synthesis:
1-Methylimidazole is used as an intermediate in the synthesis of pharmaceutical intermediates, playing a crucial role in the preparation of drugs such as losartan, nizofenone, 1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride, and naphazoline hydrochloride. It is also used in the production of pesticides.
Used in Organic Synthesis:
1-Methylimidazole serves as a precursor for the synthesis of pyrrole-imidazole polyamides and ionic liquids, such as 1-butyl-3-methylimidazolium hexafluorophosphate. It is actively involved in removing acid during the production of diethoxyphenylphosphine, contributing to the overall efficiency of the process.
Used in Catalyst and Curing Agent Production:
1-Methylimidazole is used as a catalyst in the manufacturing process of polyurethanes, a versatile polymer with a wide range of applications in various industries. Additionally, 1-Methylimidazole is utilized as a curing agent for epoxy resins, which are essential in the production of coatings, adhesives, and composite materials.
Used in Ion-Exchange Resins, Dye Intermediates, and Textile Auxiliaries:
1-Methylimidazole is employed in the production of ion-exchange resins, which are used in water treatment, food processing, and pharmaceutical industries. It is also used in the synthesis of dye intermediates, contributing to the vibrant colors in various applications. Furthermore, it serves as a component in textile auxiliaries, enhancing the quality and performance of textiles.
Used in Photographic Chemicals and Corrosion Inhibitors:
This versatile compound is used in the formulation of photographic chemicals, playing a role in the development and processing of photographic films and papers. Additionally, 1-Methylimidazole is utilized as a corrosion inhibitor, protecting metals from degradation and extending their service life in various applications.

Preparation

1-Methylimidazole is prepared mainly by two routes industrially. The main one is acid-catalysed methylation of imidazole by methanol. The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine. (CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation. Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation. H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I [H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI

Flammability and Explosibility

Notclassified

Purification Methods

Dry it with sodium metal and then distil it. Store it at 0o under dry argon. The picrate has m 159.5-160.5o (from H2O). [Beilstein 23 III/IV 568.]

InChI:InChI=1/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3

Upstream product

• 60-56-0 2-Mercapto-1-methylimidazole 
• 13222-51-0 (E)-1-N,N-dimethylamino-1-propene 
• 85702-23-4 1-Methyl-imidazoliumkation 
• 288-32-4 1H-imidazole 
• 67-56-1 methanol 
• 174501-64-5 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 
• 75-31-0 isopropylamine 
• 1066-33-7 ammonium bicarbonate 
• 74-89-5 methylamine 
• 188680-60-6 trioxane 
• 848641-49-6 1-methylimidazol diethylphosphate 
• 848641-52-1 1-ethylimidazol diethylphosphate 
• 81505-35-3 1-ethylimidazole hydrochloride 
• 35487-17-3 1-methylimidazolium chloride 

Downstream Products

• 37570-94-8 1,1'-dimethyl-2,2'-biimidazole 
• 77429-59-5 2-(1-methyl-1H-imidazol-2-yl)pyridine 
• 18197-25-6 N-methyl-N-formylformamide 
• 6642-30-4 methyl N-methylcarbamate 
• 37067-95-1 2-iodo-1-methyl-1H-imidazole 
• 37067-96-2 4,5-diiodo-1-methyl-1H-imidazole 
• 37067-97-3 2,4,5-triiodo-1-methyl-imidazole 
• 71759-88-1 5-iodo-1N-methyl imidazole 
• 86026-81-5 2,5-diiodo-1-methyl-1H-imidazole 
• 66787-69-7 2-Fluor-1-methylimidazol 
• 16681-59-7 2-bromo-1-methyl-1H-imidazole 
• 157997-38-1 1,3-Dihydro-1-methyl-2H-imidazole-2-selone 
• 13750-81-7 N-methyl-2-imidazolcarboxaldehyde 
• 30517-58-9 2-(diphenylhydroxymethyl)-1-methyl-1H-imidazole 

Relevant articles and documents

Selective N-Alkylation of Imidazole with Alcohols over Calcined Layered Double Hydroxides

Vapor-phase N-alkylation syntheses of imidazole were carried out with MeOH and EtOH over a series of calcined MgII-AlIII layered double hydroxides (LDHs) selectively produced in high yields of N-methyl (70%) and N-ethyl (63%) imidazoles only on the 3 : 1 atomic ratio of MgII-AlIII calcined LDH. Attempts on C-alkylation and dialkylation reactions over the same catalysts proved to be unsuccessful.

Evaluation of decomposition products of EMImCl·1.5AlCl3 during aluminium electrodeposition with different analytical methods

Ionic liquids are of great importance for electrodeposition of metals, which can't be deposited from aqueous electrolytes due to their negative standard potentials. In this paper non-woven polymers were coated with aluminium by electrodeposition from 1-et

Crystallographic and spectroscopic analysis of 9,10-bis-alkyl imidazolium anthracene hexatungstate supramolecular complexes

This article describes the ionic and supramolecular association of bis-dialkyl imidazolium anthracene dications with hexametalate cluster anions. In the relevant compounds, the length of the alkyl chain was varied to observe its effect on the crystal packing. Despite the endothermicity in the crystals due to structural incompatibility between planar anthracene and spherical polyoxometalate ion, packing stability is attained by coulombic interaction together with the supramolecular interactions between the components. The nature of supramolecular interactions depends on the number of carbon atoms in the alkyl chain in the organic counterparts of the crystals which ultimately modifies the packing pattern.

Reactivity of Ionic Liquids: Reductive Effect of [C4C1im]BF4 to Form Particles of Red Amorphous Selenium and Bi2Se3 from Oxide Precursors

Temperature-induced change in reactivity of the frequently used ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([C4C1im]BF4) is presented as a prerequisite for the rational screening of reaction courses in material synthesis. [C4C1im]BF4 becomes active with oxidic precursor compounds in reduction reaction at ?≥200 °C, even without the addition of an external reducing agent. The reaction mechanism of forming red amorphous selenium from SeO2 is investigated as a model system and can be described similarly to the Riley oxidation. The reactive species but-1-ene, which is formed during the decomposition of [C4C1im]BF4, reacts with SeO2 and form but-3-en-2-one, water, and selenium. Elucidation of the mechanism was achieved by thermoanalytical investigations. The monotropic phase transition of selenium was analyzed by the differential scanning calorimetry. Beyond, the suitability of the single source oxide precursor Bi2Se3O9 for the synthesis of Bi2Se3 particles was confirmed. Identification, characterization of formed solids succeeded by using light microscopy, XRD, SEM, and EDX.

N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates

Abstract: The reactions of imidazoles with a series of dialkyl and alkylene carbonatesafforded the corresponding N-alkyl- andN-(hydroxyalkyl)imidazoles with highyields. The reactivity of dialkyl carbonates decreases in the series dimethyl> diethyl > dibutyl carbonate. Ethylene carbonate is a more efficientalkylating agent than trimethylene carbonate. The mechanisms of alkylation ofimidazole with dimethyl carbonate and ethylene carbonate were studied by DFTquantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory.

Amphiphilic Polymeric Nanoparticles for Photoredox Catalysis in Water

Photoredox catalysis has recently emerged as a powerful synthesis tool in organic and polymer chemistry. In contrast to the great achievements realized in organic solvents, performing photocatalytic processes efficiently in aqueous media encounters several challenges. Here, it is presented how amphiphilic single-chain polymeric nanoparticles (SCPNs) can be utilized as small reactors to conduct light-driven chemical reactions in water. By incorporating a phenothiazine (PTH) catalyst into the polymeric scaffold, metal-free reduction and C?C cross-coupling reactions can be carried out upon exposure to UV light under ambient conditions. The versatility of this approach is underlined by a large substrate scope, tolerance towards oxygen, and excellent recyclability. This approach thereby contributes to a sustainable and green way of implementing photoredox catalysis.

Molecular tunability of surface-functionalized metal nanocrystals for selective electrochemical CO2 reduction

Organic ligands are used in homogeneous catalysis to tune the metal center reactivity; in contrast, clean surfaces are usually preferred in heterogeneous catalysis. Herein, we demonstrate the potential of a molecular chemistry approach to develop efficient and selective heterogeneous catalysts in the electrochemical CO2 reduction reaction (CO2RR). We have tailor-made imidazolium ligands to promote the CO2RR at the surface of hybrid organic/inorganic electrode materials. We used silver nanocrystals for the inorganic component to obtain fundamental insights into the delicate tuning of the surface chemistry offered by these ligands. We reveal that modifying the electronic properties of the metal surface with anchor groups along with the solid/liquid interface with tail groups is crucial in obtaining selectivities (above 90% FE for CO), which are higher than the non-functionalized Ag nanocrystals. We also show that there is a unique dependency of the CO2RR selectivity on the length of the hydrocarbon tail of these ligands, offering a new way to tune the interactions between the metal surface with the electrolyte and reactants.

Polyfunctional imidazolium surfactant and preparation method thereof

The invention discloses a polyfunctional imidazolium surfactant and a preparation method thereof. The preparation method comprises the following steps: 1) preparing an alkyl-substituted imidazole intermediate; 2) preparing a bromo-oligomer intermediate; and 3) under nitrogen protection, adding the alkyl-substituted imidazole intermediate, the bromo-oligomer intermediate and acetonitrile in a reaction bottle, stirring the materials, heating the materials and performing backflow, reacting the materials, cooling the materials to room temperature, and removing a solvent to obtain the tri-imidazolium surfactant. Compared with the prior art, the tri-imidazolium surfactant has excellent performance, has three imidazolium groups, and greatly enhances the hydrophilic performance of the surfactant.The tri-imidazolium surfactant can adjust an amount of a monomer, effectively controls a size of a hydrophobic group in the surfactant molecules, and is in favor of regulating and controlling the performance of the surfactant. The preparation method of the tri-imidazolium surfactant has the advantage of simple process, and the obtained product has the advantages of easy separating and purifying, less by-product, and environmentally friendly performance.

Novel alkylimidazolium ionic liquids as an antibacterial alternative to pathogens of the skin and soft tissue infections

Keeping in mind the concept of green chemistry, this research aims to synthesize and characterize new ionic liquids (ILs) derived from N-cinnamyl imidazole with different sizes of alkyl chains (1, 6, 8, and 10 carbon atoms), and evaluate their antibacterial activity against Skin and soft tissue infections (SSTIs) causative bacteria. The antibacterial screening was carried out by agar well diffusion and the Minimum Inhibitory Concentration (MIC) and Half Maximum Inhibitory Concentration (IC50) of the different ILs were determined by microdilution in broth, also Molecular dynamics simulations were performed to study the interaction mechanism between ILs and membranes. The MIC value in Gram-positive bacteria showed that as the hydrocarbon chain increases, the MIC value decreases with a dose-dependent effect. Furthermore, Gram-negative bacteria showed high MIC values, which were also evidenced in the antibacterial screening. The molecular dynamics showed an incorporation of the ILs with the longer chain (10 C), corresponding to a passive diffusion towards the membrane surface, for its part, the ILs with the shorter chain due to its lack of hydrophobicity was not incorporated into the bilayer. Finally, the new ILs synthesized could be an alternative for the treatment of Gram-positive bacteria causative of SSTIs.

Alkylation method for nitrogen-hydrogen containing compounds and application thereof

The invention discloses an alkylation method for nitrogen-hydrogen containing compounds and an application thereof, belonging to the technical field of synthesis of organic compounds. The invention provides a series of methods for a nitrogen alkylation reaction of N-H containing heterocyclic compounds (II) with N,N-dimethylformamide dialkyl acetal as an alkyl source under the condition of no participation of metals, and a product with a hydrogen atom on a nitrogen atom substituted by R1 is obtained. The method provided by the invention has the advantages of highly-efficient reaction, high yield, simple treatment after the reaction, simple and convenient operation, mild reaction conditions, no participation of the metals, high tolerance of functional groups of a reaction substrate, wide range and easy preparation of the substrate, high reaction efficiency after amplification of the reaction, and applicability to large-scale industrial production.