1 methylimidazole

Manufactured by Merck Group

Sourced in United States, Germany, Spain, Italy, China

1-methylimidazole is a colorless, flammable liquid organic compound used as a chemical intermediate and laboratory reagent. It has the molecular formula C₄H₆N₂. 1-methylimidazole is commonly used in the synthesis of other organic compounds and as a building block in the preparation of pharmaceuticals and other products.

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Lab products found in correlation

Ethyl acetate, by Merck Group (10 mentions) Dichloromethane, by Merck Group (9 mentions) 1 chlorobutane, by Merck Group (8 mentions) Pyridine, by Merck Group (6 mentions) Acetonitrile, by Merck Group (6 mentions) Sodium tetrafluoroborate, by Merck Group (5 mentions) Hexane, by Merck Group (5 mentions) Imidazole, by Merck Group (4 mentions) Dimethyl sulfoxide (dmso), by Thermo Fisher Scientific (4 mentions) Methanol, by Merck Group (4 mentions) Ethanol, by Merck Group (4 mentions) Hydrochloric acid (hcl), by Merck Group (4 mentions) Sulfuric acid, by Merck Group (4 mentions) 1 chlorobutane, by Thermo Fisher Scientific (4 mentions) Chloroform, by Merck Group (3 mentions) Toluene, by Merck Group (3 mentions) N n dimethylformamide (dmf), by Merck Group (3 mentions) Acetone, by Merck Group (3 mentions) Sodium chloride (nacl), by Merck Group (3 mentions) Acetic anhydride, by Merck Group (3 mentions)

93 protocols using 1 methylimidazole

Synthesis of Metal-Organic Frameworks

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Zinc nitrate hexahydrate
(≥99% purity), 2-methylimidazolate (Hmim, 99% purity), dipotassium
phosphate (≥98% purity), 1-methylimidazole (96% purity), potassium
dihydrogen phosphate (≥99% purity), glutaraldehyde solution
(25% in H₂O), titanium(IV) isopropoxide (TIPO, ≥97%
purity), tetraethylorthosilicate (TEOS, 98% purity), Pluronic P123,
and poly(styrenesulfonate) sodium salt (PSS) were purchased from Aldrich
Chemical Co. Unless noted otherwise, all chemicals were used without
further purification.

Tang Y., Dubbeldam D., Guo X., Rothenberg G, & Tanase S. (2019). Efficient Separation of Ethanol–Methanol and Ethanol–Water Mixtures Using ZIF-8 Supported on a Hierarchical Porous Mixed-Oxide Substrate. ACS Applied Materials & Interfaces, 11(23), 21126-21136.

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Synthesis and Characterization of Imidazolium Ionic Liquids

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Dimethyl sulfoxide (DMSO), silver nitrate (AgNO₃), copper chloride (CuCl₂), (3-mercaptopropyl)trimethoxysilane (MPTMS), 1-methyl imidazole, 1-butyl imidazole, bromoethane, 1-bromohexane, tetrabutylammonium bromide (TBABr), and polyvinyl butyral (PVB, Butvar® B-98) were purchased from Aldrich. All chemicals were used as received. 1-Methyl-4-hexylimidazolium bromide (MHImBr), 1-butyl-4-ethylimidazolium bromide (BEImBr), and 1-butyl-4-hexylimidazolium bromide (BHImBr) were synthesized and purified according to previous reports.^{32 –34 (link)} The structures of synthesized ILs are listed in Table 1.

Park C., Seo S., Shin H., Sarwade B.D., Na J, & Kim E. (2014). Switchable silver mirrors with long memory effects †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc01912a Click here for additional data file. Click here for additional data file.. Chemical Science, 6(1), 596-602.

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Synthesis and Characterization of Styrene-Vinylbenzyl Chloride Copolymers

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Styrene (99%, Alfa Aesar) and 4-vinylbenzyl chloride (90%, Aldrich) monomers were purified before use by passing them through basic aluminum oxide (98%, Acros Organics) to remove stabilizing agents. The chemical reagents including azobisisobutyronitrile (AIBN) (99%, Otsuka chemical), 1-methylimidazole (99%, Aldrich), N-b-hydroxyethyl oleyl imidazoline (HEOImn) (99%, Chem Service), and potassium hydroxide (>85%, Acros Organics) were used without further purifications. All the solvents used in this work such as toluene (Sigma Aldrich), dimethyl sulfoxide (DMSO) (Acros Organics), anhydrous methanol (Macron Fine Chemicals), isopropyl alcohol (Macron Fine Chemicals), chloroform (Sigma Aldrich) were ACS reagent grade. The standard solutions for the titration analysis, 0.1 M sodium hydroxide solution and 0.1 M hydrochloric acid solution, were purchased from Honeywell Fluka. Nitrogen, hydrogen, and oxygen gases with a high purity of greater than 99.99% were provided from local manufacturer (Jing-Shang gas).

Jheng L.C., Hsu C.Y, & Yeh H.Y. (2021). Anion Exchange Membranes Based on Imidazoline Quaternized Polystyrene Copolymers for Fuel Cell Applications. Membranes, 11(11), 901.

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Synthesis of Imidazolium-based Ionic Liquids

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1-Hexyl-3-methylimidazolium bromide (Aldrich, Saint Louis, MO, USA), H₃PMo₁₂O₄₀·26H₂O (99.9% Merck, Kennallsburg, NJ, USA), H₃PW₁₂O₄₀·15H₂O (purum, Aldrich), 1-methylimidazole (Aldrich), bromobutane (Aldrich), bromododecane (Aldrich), Merrifield resin (Aldrich), EtOH (Aldrich), DMF (Aldrich), dichloromethane (Aldrich), Acetone (Aldrich), Cyclohexene (Aldrich), 35% H₂O₂ (Acros, Geel, Belgium) were used as received

Pisk J., Agustin D, & Poli R. (2019). Organic Salts and Merrifield Resin Supported [PM12O40]3− (M = Mo or W) as Catalysts for Adipic Acid Synthesis. Molecules, 24(4), 783.

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Preparation of Phosphate Buffers

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Potassium acetate and potassium phosphate salts were obtained from Fisher Scientific. Imidazole, 1-methylImidazole, and 4-nitroImidazole were obtained from Aldrich Chemical Co. Buffers between pH 4.0 and 5.5 were 0.010 M acetate with added KH₂PO₄ to adjust the ionic strength. Between pH 5.5 and 8.0, the buffers were mixtures of KH₂PO₄ and K₂HPO₄, controlling ionic strength to the desired values.

Erman J.E., Chinchilla D., Studer J, & Vitello L.B. (2015). Binding of imidazole, 1-methylimidazole and 4-nitroimidazole to yeast cytochrome c peroxidase (CcP) and the distal histidine mutant, CcP(H52L). Biochimica et biophysica acta, 1854(8), 869-881.

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Potassium Salt Buffers for pH Adjustment

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Potassium acetate and potassium phosphate salts were obtained from Fisher Scientific. Imidazole, 1-methylImidazole and 4-nitroImidazole were obtained from Aldrich Chemical Co. Buffers, pH 4.0 to 5.5, were 0.010 M acetate with sufficient KH₂PO₄ to adjust the ionic strength to 0.100 M. Between pH 5.5 and 8.0, the buffers were mixtures of KH₂PO₄ and K₂HPO₄ with an ionic strength 0f 0.100 M.

Bidwai A., Ayala C., Vitello L.B, & Erman J.E. (2015). Apolar distal pocket mutants of yeast cytochrome c peroxidase: Binding of imidazole, 1-methylimidazole and 4-nitroimidazole to the triAla, triVal, and triLeu variants. Biochimica et biophysica acta, 1854(8), 919-929.

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Ramie Fiber Reinforced PLA Composites

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Pure
ramie fibers were
obtained from Stucken Melchers GmbH & Co. (Germany). l-Lactide was supplied by Purac (The Netherlands) and recrystallized
from dry toluene. Poly(ethylene glycol) monomethyl ether (PEGME) (M_n = 2000 g·mol^–1, with
a polydispersity index D̵ of 1.05) was provided
by Fluka Chemika. DBU as a metal-free catalyst was purchased from
Aldrich and distilled over barium oxide before use. Chloroform was
dried using a MBRAUN Solvent Purification System (model MB-SPS 800)
equipped with alumina drying columns. Heptane was purchased from VWR
used as received. Acetic acid was purchased from ChemLab. 1-Methylimidazole
(99%, Merck) and 11-bromoundecanol (Aldrich, 98%) were used as received.
A commercially available extrusion-grade PLA (NatureWorks 4032D) designed
especially for the production of biaxially oriented films was used
as received (M_n = 133 500 ±
5000 g·mol^–1, D̵ = 1.94
± 0.06 as determined from SEC, and 1.4 ± 0.2% d-isomer content as determined by the supplier).

Mariano M., Pilate F., de Oliveira F.B., Khelifa F., Dubois P., Raquez J.M, & Dufresne A. (2017). Preparation of Cellulose Nanocrystal-Reinforced Poly(lactic acid) Nanocomposites through Noncovalent Modification with PLLA-Based Surfactants. ACS Omega, 2(6), 2678-2688.

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Biphenyl Synthesis and Ionic Liquid Preparation

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For the CTF-biphenyl synthesis, anhydrous aluminum chloride (AlCl₃; 98.5%) was received from Arcos Organics, cyanuric chloride (99%) was obtained from Sigma-Aldrich, and biphenyl (99%) from Alfa Aesar. biphenyl was recrystallized from ethanol before usage. For the synthesis of the IL, [BMIm][NTf₂] 1-chlorobutane (99%) was purchased from Merck, 1-methylimidazole (99%) and lithium bis(trifluoromethanesulfonyl)imide (Li[NTf₂]; 99%) were obtained from Fluorochem, activated charcoal (extra pure) from Merck, and acidic aluminum oxide (150 m²/g; Brockmann grade 1) from Alfa Aesar. The solvents acetone (≥99.8%), dichloromethane (DCM; 99.99%), and ethyl acetate (≥99%) were received from Fisher Scientific; and methanol (MeOH; ≥99.8%) and tetrahydrofuran (THF; ≥99.9%) from Sigma-Aldrich. The polymer Matrimid^® 5218 (BTDA/DAPI) was provided by Huntsman Advanced Materials. The gases CO₂ (grade 4.5), CH₄ (grade 4.5), and He (grade 5.0) were received from Air Liquide.

Bügel S., Hoang Q.D., Spieß A., Sun Y., Xing S, & Janiak C. (2021). Biphenyl-Based Covalent Triazine Framework/Matrimid® Mixed-Matrix Membranes for CO2/CH4 Separation. Membranes, 11(10), 795.

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Polyphenol Quantification Protocol

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Monohydrate citric acid, ethanol (96% and absolute), acetone, chlorohydric acid (37%), sodium hydroxide (pellets), methanol (analytic grade), ammoniac (analytic grade), Folin–Ciocâlteu reagent, and monohydrate gallic acid were purchased from Scharlau (Barcelona, Spain). The 1-methylimidazole was obtained from Merck (Barcelona, Spain). Glacial acetic acid and sorbitan monolaurate (Tween^® 20) were obtained from Panreac AppliChem (Barcelona, Spain). Neocuprine, 2,2′-azino-bis(3-ethylbenzo-thiazoline-6-sulphonic acid) and potassium bromide were purchased from Sigma-Aldrich (Madrid, Spain).

Umaña M., Llull L., Bon J., Eim V.S, & Simal S. (2022). Artificial Neural Networks to Optimize Oil-in-Water Emulsion Stability with Orange By-Products. Foods, 11(23), 3750.

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Synthesis of Epoxy-Acrylate Composites

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Acrylated epoxidized soybean oil (AESO, an average number of acryloyl groups per molecule calculated from ¹H-NMR spectrum is 2.7 and 0.3 of epoxy groups), m-xylylenediamine (MXDA, 99%), 1-methylimidazole (1MI, 99%), methyltrioxorhenium (71–76%), sodium sulfite (≥98%), pyridine (99.8%) were purchased from Merck (Darmstadt, Germany). Epoxidized linseed oil (ELO, an average number of epoxy groups per triglyceride calculated from ¹H-NMR spectrum is 6) was purchased from Chemical Point UG (Oberhaching, Germany). Camelina oil was received from a private farm (Lithuania). Ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate (TPOL) was purchased from Fluorochem (Hadfield, Derbyshire, UK). Sodium chloride (99.9%), sodium sulfate, tetrahydrofuran, toluene (99%), hydrogen peroxide, acetone, and dichloromethane (99%) were purchased from Eurochemicals (Kuprioniskes, Lithuania). All materials were used as received.

Petrauskas R., Grauzeliene S, & Ostrauskaite J. (2023). Thermo-Responsive Shape-Memory Dual-Cured Polymers Based on Vegetable Oils. Materials, 17(1), 24.

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