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17 protocols using 1 chlorobutane

1

Extraction and Analysis of Carotenoids

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Reagents and solvents of analytical grade used during carotenoid extraction were purchased from Synth (Diadema, Brazil). 1-Methylimidazole and 1-chlorobutane, used for the 1-butyl-3-methylimidazolium chloride ([C4mim]Cl) synthesis, were obtained from Sigma-Aldrich (Taufkirchen, Germany). MS-grade methanol (MeOH), methyl tert-butyl ether (MTBE), and water were purchased from Merck (Darmstadt, Germany). The samples were filtered through Millipore (Billerica, MA, USA) membranes (0.22 μm) before HPLC-MS analyses. The standards of (all-E)-β-carotene and (all-E)-lutein were purchased from Extrasynthese (Genay, France).
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2

Analytical Standards for AB-FUBINACA

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The AB‐FUBINACA reference standard and AB‐FUBINACA‐d4 internal standard were purchased from Cayman Chemical (Ann Arbor, MI). Solvents, salts, and other liquids such as isopropanol, 1‐chlorobutane, ammonium formate, magnesium sulfate, dimethyl sulfoxide, ammonium hydroxide, and acetic acid were purchased from Sigma–Aldrich (St. Louis, MO). GC/GC–MS grade methanol was obtained from Honeywell Burdick and Jackson (Morristown, NJ). Test tubes were obtained from Fisher Scientific (Pittsburgh, PA).
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3

Chitin Derivative Synthesis and Characterization

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All experiments described here used α-chitin isolated from snow crabs, in the form of fine powder with particle size < 200 µm, molecular weight > 2000 kDa and acetylation degree > 80% (Heppe Medical Chitosan GmbH, Germany). 1-Methylimidazole (purity 99%), 1-chlorobutane (purity 99%), acetic acid (purity 99%) and Dowex Monosphere resin 550A (OH) were obtained from Sigma-Aldrich (St. Louis, MO, USA). All solvents (methanol of purity 99.5%, acetonitrile of purity 99.5%, ethyl acetate of purity 99%) were purchased from Avantor (Gliwice, Poland) and used without further purification.
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4

Synthesis of Ionic Liquids and Reagents

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Acetonitrile
(99.9%), dichloromethane (99.8%), ethyl acetate (99.5%), 1-methylimidazole
(99%), 1-bromodecane (98%), 1-chlorobutane (98%), hexane (99.7%),
1-hexene (99.8%), 2-hexyne (99%), methyl tiglate (99%), PEG, silver
nitrate ([Ag+][NO3], 99%),
[Ag+][NTf2] (97%), silver
tetrafluoroborate ([Ag+][BF4], 98%), silver trifluoromethanesulfonate ([Ag+][TfO], 99%), 1-butyl-3-methylimidazolium nitrate ([BMIM+][NO3], 95%), [BMIM+][TfO] (95%), and [BMIM+][BF4] (97%) were purchased from Sigma-Aldrich (St.
Louis, MO, USA). Sodium tetrafluoroborate ([Na+][BF4], 97%) was purchased from Acros Organics
(Morris Plains, NJ, USA). [Li+][NTf2] (99.5%) salt was obtained from SynQuest Laboratories (Alachua,
FL, USA). Naphthalene (98%) and untreated fused silica capillary tubing
(I.D. 250 μm) were purchased from Supelco (Bellefonte, PA, USA).
All chemicals were used as received.
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5

Synthesis and Characterization of Ionic Liquid

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Bis(cycloocta-1,5-diene)nickel(0) (Ni(COD)2), 1,4 dicyanobenzene (98%) and 1-chlorobutane (>99%) were obtained from Sigma Aldrich, ZnCl2 (>98%) from Alfa Aesar and bis(trifluoromethane)sulfonimide lithium salt (99%) from ABCR. All materials were used without further purification. 1-Methylimidazole (>99%) was obtained from Sigma Aldrich, purified via fractional distillation and dried over molecular sieves for several days. Water was purified using the Millipore® system. The ionic liquid (IL) 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIm][NTf2]) was synthesized in two steps following a literature procedure [67 (link)]. The anion purity of IL by ion chromatography was found to be above 99% and the water content of the IL by Karl-Fischer titration was less than 10 ppm.
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6

Analytical Methods for FEN and FEN-D5

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Analytical grade FEN and FEN-D5 were purchased from Sigma-Aldrich (Darmstadt, Germany). Acetonitrile (J.T.Baker, Gliwice, Poland), 1-chlorobutane (Sigma-Aldrich, Darmstadt, Germany) and ammonia solution 25% (Stanlab, Lublin, Poland) were of HPLC or analytical grade. Formic acid and methanol were obtained from Sigma-Aldrich (Darmstadt, Germany) and were of analytical grade and LC-MS grade, respectively. Ultrapure water was filtered through a Millipore Milli-Q system (Burlington, MA, USA).
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7

Synthesis of Metal-Organic Frameworks

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N-Methylimidazole (> 99%), 4-Methylpyridine (> 98%), Potassium thiocyanate (> 98%), sodium tetrafluoroborate (> 98%), 1-Chlorobutane (> 99%), and 1-Bromobutane (> 99%) were obtained from Sigma–Aldrich. Ethyl acetate (> 99%), Toluene (> 99%), Ethanol (> 99%) and were obtained from Merck. Aluminum nitrate (Al(NO3)3·9H2O) (> 99%), and Terephthalic acid (> 98%) were purchased from Merck products. CO2 gas (> 99%) was used in gas absorption tests.
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8

Sodium Carbonate Protein Characterization

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Sodium carbonate (Na2CO3) was purchased from EMD Chemicals Inc. (Gibbstown, NJ). Methanol (MeOH, HPLC grade), lithium bromide (LiBr), hydrochloric acid (HCl, 6N), phosphate buffered saline (PBS) and dialysis cassettes (Slide-A-Lyzer, MWCO 3500) were purchased from ThermoFisher Scientific (Waltham, MA). Sodium hydroxide (NaOH, pellets) was purchased from VWR International, LLC. (Radnor, PA). Tris-Acetate SDS Running Buffer and NuPAGE™ LDS Sample Buffer was purchased from Novex (Carlsbad, CA). NuPAGE™ 7% Tris-Acetate Gel, Sample Reducing Agent, and HiMark™ Pre-stained HMW Protein Standard were purchased from Invitrogen (Carlsbad, CA). Iodoacetic acid (97%) was purchased from ACROS Organics/Fisher Scientific (Hampton, NH), while 3-chloro-1-propanol (98%) and 1-chlorobutane (99%) were purchased from Sigma Aldrich (St. Louis, MO).
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9

MDPBP·HCl and Methamphetamine-D5 Analysis

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Methanolic solution of 3,4-methylenedioxy-α-pyrrolidinobutiophenone hydrochloride (MDPBP·HCl) at concentration 1.0 mg/cm3 (as a free base) was purchased from Cayman Chemicals (Ann Arbor, MI, USA) and rac-methamphetamine-D5 (mAMP-D5) at concentration 0.1 mg/cm3 was obtained from LGC Standards (London, United Kingdom). Both solutions were used as standards.
All solvents used were of HPLC grade purity and were obtained from SIGMA ALDRICH (St. Louis, USA). Trifluoroacetic anhydride (TFAA) and 1-chlorobutane were ≥99 % purity (analytical grade) and were also purchased from SIGMA ALDRICH. Deionized water was purified with a Synergy 185 ultra-pure water system (Millipore, Milford, MA, USA). Hydrochloric acid at concentration 35–38 %, potassium carbonate (K2CO3), and sodium chloride (NaCl) were of analytical grade and were obtained from POCH (Gliwice, Poland). The 5 mol/dm3 K2CO3 and saturated NaCl solutions were prepared by dissolving above-mentioned salts in deionized water.
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10

Synthesis of Ionic Liquids from Alkyl Halides

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The following chemicals were used for the synthesis of ILs: 1-bromobutane (Sigma-Aldrich, 99%), 1-bromooctane (Acros Organics, 99%), 1-bromododecane (Acros Organics, 98%), triethylamine (Acros Organics, 99% pure), 1-methylimidazole, 1-chlorobutane (Sigma Aldrich, 99,5%), diethylether (Lach-Ner, 99%), n-pentane (Penta, p.a.). The 1-methylimidazole was purified by distillation and drying with potassium hydroxide. The other chemicals were used as received.
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