Tetra-methylammonium bromide (Loba Chemie, 98%), 1-methylimidazole (C4H6N2) (Alfa Aesar, 99.0%), 1,2-dimethylimidazole (Sigma Aldrich, 98%), Bromoethane (C2H5Br) (99.0%), n-Butyl Bromide (C4H9Br) (96.0%), n-Hexyl Bromide (C6H13Br) (99.0%), Octyl Bromide (C8H17Br) (98.5%) of Himedia brand were used. Ethyl Acetate (99.5%), Acetonitrile (99.5%), Dichloromethane (99.5%) were purchased from Loba Chemie and Silver Nitrate from Fisher Scientific brands were used. 1-ethyl-3-methylimidazolium bromide [Emim][Br], 1-ethyl-2,3-dimethylimidazolium bromide [Edmim][Br], 1-butyl-3-methylimidazolium bromide [Bmim][Br], 1-hexyl-3-methylimidazolium bromide [Hmim][Br] and 1-octyl-3-methylimidazolium bromide [Omim][Br] were prepared by modifying the previously reported methods (Ghosh and Mudring, 2016 (link); Kumar et al., 2017 (link)). Synthesis procedure of the above mentioned ionic liquids (ILs) in detail is followed as:
Bromoethane
Manufactured by Merck Group
Sourced in United States
Bromoethane is a colorless, volatile, and flammable liquid chemical compound. It is primarily used as a laboratory reagent and solvent in various scientific and industrial applications.
Automatically generated - may contain errors
Lab products found in correlation
Ethyl acetate, by Merck Group (2 mentions)
1 methylimidazole, by Merck Group (2 mentions)
Phenothiazine, by Thermo Fisher Scientific (2 mentions)
1 bromohexane, by Merck Group (2 mentions)
1 methylimidazole, by Thermo Fisher Scientific (1 mentions)
1 2 dimethylimidazole, by Merck Group (1 mentions)
Silver nitrate, by Thermo Fisher Scientific (1 mentions)
Acetonitrile, by Loba Chemie (1 mentions)
Dichloromethane, by Loba Chemie (1 mentions)
Ethyl acetate, by Loba Chemie (1 mentions)
P toluenesulfonic acid, by Merck Group (1 mentions)
α bromoisobutyryl bromide, by Merck Group (1 mentions)
Sulfuric acid, by Merck Group (1 mentions)
Sodium bicarbonate, by Merck Group (1 mentions)
Hydrogen peroxide, by Merck Group (1 mentions)
Maleic anhydride, by Merck Group (1 mentions)
Abietic acid, by Merck Group (1 mentions)
Copper sulfate pentahydrate, by Merck Group (1 mentions)
N n diethylethanamine, by Merck Group (1 mentions)
1 bromododecane, by Thermo Fisher Scientific (1 mentions)
13 protocols using bromoethane
1
Synthesis of Imidazolium-based Ionic Liquids
2
Multifunctional Polymeric Materials Synthesis
3
Synthesis of Organic Compounds
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Anhydrous glycerin (≥99.5%), pa M = 92.10 g/mol from Chempur (Piekary Slaskie, Poland); sodium carbonate, anhydrous (≥99.5%), pa M = 105.99 g/mol, acetic acid (≥99.5%), pa M = 60.05 g/mol, and sodium hydrogen phosphate (≥99.5%), pa M = 141.96 g/mol from POCH (Gliwice, Poland); and nitrogen (Messer, Chorzów, Poland) were purchased. In turn, 1-methylimidazole (≥99%), pa M = 82.10 g/mol, bromoethane (≥98%), pa M = 108.97 g/mol, and N,N-diethylethanamine (≥99%), pa M = 101.19 g/mol was purchased from Sigma Aldrich (Poznań, Poland), and a 1-bromotetradacane (≥98%), pa M = 277.28 g/mol and 1-bromododecane (≥98%), pa M = 249.23 g/mol in Acros Organics (Geel, Belgium); were purchased from POCH (Gliwice, Poland). All reagents were used without further purification.
4
Synthesis of Organic Compounds
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Example 2
2-Bromotoluene was purchased from Oakwood Products. Urea, bromoethane, 2-bromopropane, tetrabutylammonium hexafluorophosphate, tris(4-bromophenyl)aminium hexachloroantimonate, anhydrous toluene, and anhydrous p-dioxane were purchased from Sigma Aldrich. Phenothiazine, sodium hydride (60% dispersion in mineral oil), bis(dibenzylideneacetone)palladium(0), sodium tert-butoxide, sulfur, iodine, o-dichlorobenzene (ODCB), anhydrous dichloromethane (DCM), anhydrous tetrahydrofuran, anhydrous N,N-dimethylformamide (DMF), and magnesium sulfate were obtained from Acros Organics. Tri-tert-butylphosphonium tetrafluoroborate was obtained from Oxchem. Silica gel and neutral alumina used for column chromatography were purchased from Silicycle and Sorbent Technologies, respectively. Ethyl acetate, hexanes, and diethyl ether were purchased from VWR. Solvents used for NMR spectroscopy were obtained from Cambridge Isotope Laboratories.
5
Hydrogel Polymer Synthesis Protocols
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N,Nʼ-methylenebis(acrylamide) (MBAA, 99%; Sigma-Aldrich), poly(ethyleneglycol)diacrylate (PEGDA, Mn = 250, 575, 700; Sigma-Aldrich); ethyleneglycoldimethacrylate (≥97%; TCI), N,N,Nʼ,Nʼ-tetramethylethylendiamine (TMEDA, ≥99.5%; Sigma-Aldrich), ammoniumpersulfate (APS, 98%; Roth), 3-sulfopropylmethacrylate potassium (98%; Sigma-Aldrich), 3-sulfopropylacrylate potassium (Sigma-Aldrich), 2-acrylamido-2-methyl-1-propanesulfonicacid (99%; Sigma-Aldrich), (vinylbenzyl)trimethylammonium chloride (99%; ACROS Organics), [2-(acryloyloxy)ethyl]trimethylammonium chloride (80 wt.% in H2O; Aldrich), [2-(methacryloyloxy)ethyl]trimethylammonium chloride (75 wt.% in H2O; Aldrich), 2-hydroxyethylmethacrylate (97%; Alfa Aesar), [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammoniumhydroxide (95%; Sigma-Aldrich), 2-methacryloyloxyethylphosphorylcholine (97%; Sigma-Aldrich), 1-vinylimidazole (≥99%; Alfa Aesar), bromoethane(≥99%; Sigma-Aldrich), amino-2-propanol(93%; TCI), methacrylicanhydride (94%; Alfa Aesar) were all used as received without further treatment. 1-Vinyl-3-ethyl-imidazoliumbromide (VEtImBr) and 2-Hydroxypropyl methacrylamide (HPMAA) were prepared according to published procedures.[21 (link),22 (link)]
6
Synthesis of PS-b-P2VP Block Copolymer
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A PS-b-P2VP was synthesized via living anionic polymerization (36 ). The number average molecular weight of the PS-b-P2VP BCP was 126 kg mol−1 [Φps = 0.49, polymer dispersity index (PDI) = 1.05]. PGMEA, chloroform, ethanol, PEGDA (Mn = 700), HOMPP, Triton X-100, EMIMTFSI, LiTFSI, bromoethane, 1,4-dibromobutane, and hydrobromic acid were purchased from Sigma-Aldrich.
7
Synthesis of Functionalized Silicone Catheters
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N-vinylimidazole/NVI, 99% (Sigma-Aldrich, Saint Louis, MO, USA). Medical-grade silicone catheters, 3 m, inner diameter 2.0 mm and outer diameter 5.0 mm (Goodfellow, Cambridge, UK). Ampicillin, 99% (Sigma-Aldrich, Saint Louis, MO, USA). Iodomethane, 99% (Sigma-Aldrich, Saint Louis, MO, USA). Bromoethane, 98% (Sigma-Aldrich, Saint Louis, MO, USA). Silver nitrate, 99% (Sigma-Aldrich, Saint Louis, MO, USA). Methanol, 99.5% (J.T. Bake, Mexico City, Mexico).
8
Synthesis and Purification of Halogenated Organic Compounds
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Bromoethane
98%,1-Bromopropane 99%, 1-bromobutane
99%, 1-bromopentane 98%, 1-bromohexane 98%, 1-bromoheptane 99%, 1-bromooctane
99%, 1-bromononane 98%, 1-bromodecane 98%, 1-bromododecane 97%, 1-bromotetradecane
97%, 1-bromohexadecane 97%, 1-bromooctadecane 97%, and betaine 99%
were purchased from Sigma-Aldrich (Saint Louis, MO, USA). Iodosulfuron-methyl
sodium salt (purity 96.6%) was obtained from PESTINOVA (Jaworzno,
Poland). All solvents (methanol, DMSO, acetonitrile, acetone, isopropanol,
ethyl acetate, chloroform, toluene, hexane) and potassium hydroxide
were obtained from Avantor (Gliwice, Poland) and used without further
purification. Deionized water with a conductivity of <0.1 μS
cm–1, from Hydrolab HLP Smart 1000 demineralizer
(Straszyn, Poland), was used.
98%,1-Bromopropane 99%, 1-bromobutane
99%, 1-bromopentane 98%, 1-bromohexane 98%, 1-bromoheptane 99%, 1-bromooctane
99%, 1-bromononane 98%, 1-bromodecane 98%, 1-bromododecane 97%, 1-bromotetradecane
97%, 1-bromohexadecane 97%, 1-bromooctadecane 97%, and betaine 99%
were purchased from Sigma-Aldrich (Saint Louis, MO, USA). Iodosulfuron-methyl
sodium salt (purity 96.6%) was obtained from PESTINOVA (Jaworzno,
Poland). All solvents (methanol, DMSO, acetonitrile, acetone, isopropanol,
ethyl acetate, chloroform, toluene, hexane) and potassium hydroxide
were obtained from Avantor (Gliwice, Poland) and used without further
purification. Deionized water with a conductivity of <0.1 μS
cm–1, from Hydrolab HLP Smart 1000 demineralizer
(Straszyn, Poland), was used.
9
Synthesis and Characterization of Fluorinated Compounds
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Example 2
Overall Experimental
Bromoethane, copper(I) oxide, bromine, anhydrous N,N-dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), charcoal, and 1,4-dioxane were purchased from Sigma Aldrich. Phenothiazine and copper iodide were obtained from Acros Organics. Sodium hydride, sodium acetate, and acetic acid were purchased from Alfa Aesar. Pentafluorothiophenol and sodium pentafluoropropionate were purchased from Oakwood Chemical, iron powder from Mallinckrodt Pharmaceuticals, 2,3,4,5-tetrafluoroaniline from AK Scientific, potassium hydroxide and celite from Fisher Scientific, and ethanol from Decon Labs. All reagents were used without further purification.
Silica gel (65×250 mesh) was purchased from Sorbent Technologies, and solvents for purification were purchased from VWR International. 1H, 19F and 13C NMR spectra were obtained on 400 MHz Varian NMR spectrometers in DMSO-d6, acetone-d6 or CDCl3 purchased from Cambridge Isotope Laboratories. 19F NMR spectra were recorded in CDCl3 using hexafluorobenzene (Alfa Aesar) as an internal standard, and the chemical shifts are reported vs. CFCl3 at 0 ppm by adjusting the shift of hexafluorobenzene to −164.9 ppm. Mass spectra were obtained on an Agilent 5973 Network mass-selective detector attached to Agilent 6890N Network GC system. Elemental analyses were performed by Atlantic Microlab, Inc.
10
Synthesis and Preparation of OIPCs and ILs
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Triethylmethylammonium chloride ([N1222][Cl] (>97 %, Sigma Aldrich), lithium difluoro(oxalato)borate ([Li][DFOB]) (Sigma Aldrich), N,N‐ethyl‐methylpyrrolidinium 4‐methylbenzenesulfonate ([C2mpyr][Ts]) (>99 %, Boron Molecular), N‐methylpyrrolidine (>99.5 %, Sigma Aldrich), bromoethane (>98 %, Sigma Aldrich), triethylmethylphosphonium tosylate ([P1222][Ts], >98 % Cytec Industries), isobutyldiethylmethylphosphonium ([P122i4][Ts], >98 %, Cytec Industries), methyl p‐toluenesulfonate (>99 %, Boron Molecular), triethylamine (Boron Molecular) were used as received. All OIPCs and ILs were dried for at least 48 hours at room temperature under vacuum (ca. 0.1 mbar) in order to ensure that water had been completely removed, with subsequent handling and sample preparation in an Argon glove box.
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