1 butylimidazole

Manufactured by Merck Group

Sourced in Germany

1-butylimidazole is a chemical compound used in various laboratory applications. It is a colorless liquid with a characteristic odor. 1-butylimidazole serves as a precursor and intermediate in organic synthesis reactions.

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Lab products found in correlation

Toluene, by Merck Group (2 mentions) 1 methylimidazole, by Merck Group (2 mentions) Isopropoxide, by Merck Group (1 mentions) 2 2 azobisisobutyronitrile, by Merck Group (1 mentions) 4 chloromethylstyrene, by Merck Group (1 mentions) Chloroplatinic acid hexahydrate h2ptcl6, by Merck Group (1 mentions) Sodium hydroxide (naoh), by Merck Group (1 mentions) Magnesium sulfate mgso4, by Merck Group (1 mentions) Lithium iodide, by Merck Group (1 mentions) Methanol, by Thermo Fisher Scientific (1 mentions) Ultrasil 7000 gr, by Evonik (1 mentions) Dimethyl sulfoxide d6, by Cambridge Isotopes (1 mentions) 1 chloropentane, by Merck Group (1 mentions) Ethyl acetate, by Merck Group (1 mentions) Benzyl chloride, by Merck Group (1 mentions) Tetrahydrofuran, by Thermo Fisher Scientific (1 mentions) Acetonitrile, by Thermo Fisher Scientific (1 mentions) Azobis, by Merck Group (1 mentions) Deuterated chloroform, by Thermo Fisher Scientific (1 mentions) Lithium bis, by Merck Group (1 mentions)

7 protocols using 1 butylimidazole

Synthesis of Polymer-Based Solar Cells

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Poly(vinyl chloride) (PVC, M_w = 97,000 g mol⁻¹, M_n = 55,000 g mol⁻¹), poly(oxyethylene methacrylate) (POEM, poly(ethylene glycol) methyl ether methacrylate, M_n = 475 g mol⁻¹), 1,1,4,7,10,10-hexamethyltriethylene tetramine (HMTETA, 99%), copper(I) chloride (CuCl, 99%), titanium(IV) isopropoxide (TTIP, 97%), hydrogen chloride solution (HCl, 37 wt %), sodium hydroxide (NaOH), 1-butylimidazole, 4-chloromethylstyrene, lithium iodide (LiI), magnesium sulfate (MgSO₄), 2,2′-azobisisobutyronitrile (AIBN), and chloroplatinic acid hexahydrate (H₂PtCl₆) were purchased from Sigma-Aldrich (St. Louis, MO). Tetrahydrofuran (THF), N-methyl pyrrolidone (NMP), methanol, 2-propanol, chloroform, acetonitrile, diethylether, and ethyl acetate were purchased from J.T. Baker. Deionized water (>18 MΩ·m) was obtained with a water purification system made by the Millipore Corporation. Ruthenium dye (535-bisTBA, N719) and TiO₂ colloidal paste (Ti-Nanoxide, D20) were purchased from Solaronix, Switzerland. Fluorine-doped tin oxide (FTO) conducting glass substrate (TEC8, 8 ohms/sq, 2.3 mm thick) was purchased from Pilkington, France. The purities of chemicals employed in this work were higher than 99%, and all chemicals were utilized without additional purification.

Park J.T., Chi W.S., Kim S.J., Lee D, & Kim J.H. (2014). Mesoporous TiO2 Bragg Stack Templated by Graft Copolymer for Dye-sensitized Solar Cells. Scientific Reports, 4, 5505.

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Bromobutyl Rubber Functionalization Protocol

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1-Butylimidazole (1) (Sigma-Aldrich, 98%), n-propyltriethoxysilane (A₁) (abcr, 97%), (3-bromopropyl)trimethoxysilane (A₃) (abcr, 97%), toluene (Aldrich, anhydrous 99.8%), and methanol (Acros Organics, 99.9%) were used as received. Precipitated silica Ultrasil® 7000 GR (S₀) with a specific surface area (BET) of 175 m² g⁻¹ and a primary particle size of 10 nm was supplied by Evonik Industries. Bromobutyl rubber (BIIR) is a commercial product of Lanxess with a bromine content of 1.13 wt% (0.80 mol% brominated isoprene units) determined by ¹H NMR. Ionically modified bromobutyl rubber (BIIR-i) was obtained by conversion of BIIR with 1 (see Scheme 1) as described earlier.^{19,20 (link)}

Sallat A., Das A., Schaber J., Scheler U., Bhagavatheswaran E.S., Stöckelhuber K.W., Heinrich G., Voit B, & Böhme F. (2018). Viscoelastic and self-healing behavior of silica filled ionically modified poly(isobutylene-co-isoprene) rubber. RSC Advances, 8(47), 26793-26803.

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Synthesis and Characterization of Ionic Liquids

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1-butylimidazole (98%, Sigma-Aldrich), 1-chloropentane (99%, Sigma-Aldrich), potassium trifluoromethanesulfonate (KOTf, Sigma-Aldrich), sodium tetrafluoroborate (NaBF₄, Sigma-Aldrich), benzyl chloride (99%, Sigma-Aldrich), dimethyl sulfoxide-D₆ (DMSO‑d₆, 99.9%) + 0.05% V/V tetramethylsilane (TMS, Cambridge Isotope Laboratories, Inc.), NH₃ (99.99%), Ar gas (99.99%), and ethyl acetate (99.5%, Sigma-Aldrich) (Table 1) were used as received without any purification.Table 1

Materials for IL synthesis and characterization.

Table 1

Materials	Molecular formula	CAS Number	Purity	Company
1-butylimidazole	C₇H₁₂N₂	4316-42-1	98%	Sigma-Aldrich
1-chloropentane	C₅H₁₁Cl	543-59-9	99%
Potassium trifluoromethanesulfonate	CF₃KO₃S	2926-27-4	98%
Sodium tetrafluoroborate	NaBF₄	13755-29-8	98%
ethyl acetate	C₄H₈O₂	141-78-6	99.5%
Dimethyl sulfoxide-D₆+0.05% V/V tetramethylsilane	C₂H₆OS + Si(CH₃)₄	2206-27-1	99.9%	Cambridge Isotope Laboratories, Inc.
Ammonia	NH₃	–	99.9%	–
Argon	Ar	–	99.9%	–

Salman M., Lee J.W., Lee S.H., Lee M.H., Pham V.D., Kim M.S., Cho D, & Lee H.J. (2024). A comparative study of ammonia solubility in imidazolium-based ionic liquids with different structural compositions. Heliyon, 10(2), e24305.

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Synthesis of Amphiphilic Copolymers

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4-Cyano-4-[(dodecylsulfanyl-thiocarbonyl)sulfanyl]pentanoic
acid (chain transfer agent (CTA), >97%), benzene (anhydrous), 1-butylimidazole
(98%), and lithium bis(trifluoromethanesulfonyl)imide (LiTFSI, 97%)
were used as received from Sigma-Aldrich. Dichloromethane (DCM, 99.9%,
HPLC), 4-vinylbenzyl chloride (VBC, 90%), diethyl ether anhydrous
(BHT Stabilized/Certified ACS), aluminum oxide (anhydrous), methanol
(≥99.8%, ACS Certified), N,N-dimethylformamide (DMF, 99%), acetonitrile (anhydrous, 99.9%), deuterated
chloroform (CDCl₃, 99.8 atom % D), dimethyl-d6 sulfoxide
(DMSO-d6, 99.9 atom % D), and tetrahydrofuran (THF, ≥ 99.9%,
Optima for HPLC) were used as received from Fisher Scientific. Azobis(isobutyronitrile)
(AIBN, 98%, Sigma-Aldrich) was purified by recrystallization from
methanol. Styrene (S, 99%, Fisher Scientific) was purified of inhibitor
by passing through a column packed with aluminum oxide.

Coote J.P., Adotey S.K., Sangoro J.R, & Stein G.E. (2023). Interfacial Effects in Conductivity Measurements of Block Copolymer Electrolytes. ACS Polymers Au, 3(4), 331-343.

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Synthesis of Ionic Liquid-Based Polymer

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All compounds and solvents were commercially available and used as received: 2-bromoethanol (Aldrich, Steinheim, Germany, 95%), triethylamine (Sigma Aldrich, Munich, Germany, 99%), methacryloyl chloride (Aldrich, 97%), 1-butylimidazole (Aldrich, 98%), hydroquinone (Panreac, Barcelona, Spain, 99.5%), methyl methacrylate, 1-vinyl-2-pyrrolidone, bis(trifluoromethane)sulfonamide lithium salt (Aldrich, 99.95%), milliQ water, dichloromethane (Aldrich, 99.99%), hexane (Scharlau, Bavaria, Germany, 99.8%), Uralumina150 (U150) (Scionix Ltd. (London, UK)), and urea (Fischer Scientific, Madrid, Spain, 99.5%).

Pablos J.L., Tiemblo P., Ellis G, & Corrales T. (2021). Chloroaluminate Gel Electrolytes Prepared with Copolymers Based on Imidazolium Ionic Liquids and Deep Eutectic Solvent AlCl3:Urea. Polymers, 13(7), 1050.

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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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Purification and Handling of Imidazole Compounds

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1-Methylimidazole (Sigma-Aldrich, 99%) and 1-butylimidazole (Aldrich, 99%) were distilled under vacuum from potassium hydroxide (Akzo Nobel, 87.9%). 1-Chlorobutane (Acros Organics, 99%), allyl chloride (Aldrich, 99%) and dimethylsulfate (Fluka, 95%) were distilled from CaO (Sigma-Aldrich). Ethyl acetate (Fisher Chemicals HPLC) and acetonitrile (Fisher Chemicals HPLC) were dried by running them through neutral aluminum oxide 90 (Merck 70–230 mesh ASTM) and toluene (Sigma-Aldrich, 99.7%) through silica (Acros Organics, Ultrapure 40–60 μm, 60A). All starting materials were used within hours of preparation. All reactions and washing procedures were carried out in dry glassware with dried chemicals and under inert atmosphere (argon) if not stated otherwise or in the case where water was used.

Gräsvik J., Winestrand S., Normark M., Jönsson L.J, & Mikkola J.P. (2014). Evaluation of four ionic liquids for pretreatment of lignocellulosic biomass. BMC Biotechnology, 14, 34.

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