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27 protocols using tetrahydrofuran

1

Synthesis and Purification of Bromopurine Derivatives

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6-Bromopurine was purchased from Sigma-Aldrich/Merck (St. Louis, MO, USA). 6-Bromo-9-methylpurine and 6-bromo-7-methylpurine were synthesized as described previously (Okamura et al. 2009a (link), b (link)). Chloroform (CHCl3, dehydrated) and super dehydrated solvents—acetone (ACT), acetonitrile (MeCN), ethyl acetate (AcOEt), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), 1,4-dioxane (1,4-DO), diisopropyl ether (iPr2O), toluene (Tol), and dichloromethane (DCM)—were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Methyl acetate (AcOMe, anhydrous) and 1,3-dioxane (1,3-DO) were purchased from Sigma-Aldrich/Merck. Methyl propionate (MP, special grade) was purchased from FUJIFILM Wako Pure Chemical Corporation. 2-Methyltetrahydrofuran (2-MeTHF, dehydrated) was purchased from KANTO CHEMICAL Co., INC (Tokyo, Japan). Aqueous 57% hydrogen iodide (HI) solution was purchased from FUJIFILM Wako Pure Chemical Corporation. Potassium Carbonate (K2CO3, guaranteed reagent) was purchased from FUJIFILM Wako Pure Chemical Corporation and was ground in a mortar into a fine powder, which was used for manual and automated syntheses. A 0.05–0.08 M solution of lithium aluminum hydride (LAH) in THF was prepared by diluting a 1.0 M solution of LAH in THF, which was purchased from Sigma-Aldrich/Merck.
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2

Sensitive HPLC Quantification of Colistin and Netilmicin

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Analytical grade colistin sulfate, netilmicin sulfate, 9-fluorenylmethyl chloroformate (FMOC-Cl), trichloroacetic acid, sodium hydroxide, acetone, sodium hydrogen carbonate, and boric acid, and HPLC grade methanol, acetonitrile, tetrahydrofuran, and distilled water were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). The serum employed for quality control (QC) was purchased from Alfresa Pharma Corporation (Osaka, Japan).
Stock solutions of colistin sulfate (100 μg/mL) and netilmicin sulfate (5 μg/mL) internal standard were prepared by dissolving 1.0 and 0.05 mg of the respective substances in 10 mL of distilled water. A 100 mM FMOC-Cl stock solution was prepared by dissolving 258.7 mg of FMOC-Cl in 10 mL of acetonitrile. The carbonate buffer (1 wt%, pH 10) was prepared by dissolving the sodium hydrogen carbonate (1 g) in distilled water (100 mL) and the pH of the solution was adjusted to 10 using sodium hydroxide. All solutions were stable for at least 2months when stored in a refrigerator at 4 °C.
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3

Cellulose Valorization with Supported Catalysts

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Cellulose was purchased from Merck & Co., Inc. Charcoal-supported Pd, Pt, Rh, and Ru (5 wt% metal loading; denoted as Pd/C, Pt/C, Rh/C, and Ru/C, respectively), d-glucose, d-xylose, tetrahydrofuran (THF), 1-propanol, and 1-butanol were purchased from FUJIFILM Wako Pure Chemical Corporation. Xylan (from Maple) was purchased from Tokyo Chemical Industry Co., Ltd.
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4

Ethylene Polymerization via Magnetic Stirring

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Example 5

A magnetic stirrer bar, 1.16 g of the base composition prepared in the above [Preparation of Base Composition], 0.80 g of MXDA (available from available from Tokyo Chemical Industry Co., Ltd.), and 5.57 g of tetrahydrofuran (available from Fujifilm Wako Pure Chemical Corporation, super dehydrated, stabilizer-free grade) were inserted into a 30 mL autoclave under an argon atmosphere. The autoclave was then placed in a 1° C. water bath and stirred at 700 rpm for 15 minutes to bring the reaction solution temperature to 3° C. While stirring was continued in the water bath, the autoclave was connected to an ethylene gas cylinder, and filled with ethylene gas (available from Japan Fine Products Corporation, ethylene purity: more than 99.9 vol. %) to a pressure of 2.0 MPa. The temperature of the water bath was changed to 20° C., and the reaction was carried out at 700 rpm for 24 hours. The reaction was stopped by adding 4 mL of isopropyl alcohol to the reaction solution, and the base composition was removed using a syringe filter (hole diameter of 0.45 μm, made of PTFE), and was subjected to gas chromatography analysis. The results are shown in Table 2.

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5

Ethylene Polymerization with MXDA

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Example 7

A magnetic stirrer bar, 1.16 g of the base composition prepared in the above [Preparation of Base Composition], 0.80 g of MXDA (available from available from Tokyo Chemical Industry Co., Ltd.), and 5.57 g of tetrahydrofuran (available from Fujifilm Wako Pure Chemical Corporation, super dehydrated, stabilizer-free grade) were inserted into a 30 mL autoclave under an argon atmosphere. The autoclave was placed in a water bath at 20° C. and stirred at 700 rpm, the reaction solution temperature was adjusted to 20° C., and the autoclave was connected to an ethylene gas cylinder and filled with ethylene gas (available from Japan Fine Products Corporation, ethylene purity: more than 99.9 vol. %) to a pressure of 2.0 MPa. The reaction was carried out at 700 rpm for 24 hours after the ethylene filling. The reaction was stopped by adding 4 mL of isopropyl alcohol to the reaction solution, and the base composition was removed using a syringe filter (hole diameter of 0.45 μm, made of PTFE), and was subjected to gas chromatography analysis. The results are shown in Table 2.

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6

Diverse Chemical Standards Characterization

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As test chemicals, anthraquinone (AQ), 2-ethylanthraquinone (2-EA), dibenzofuran (DF), and bis(2-ethylhexyl)phthalate (Bis) were purchased from Tokyo Chemical Industry (Tokyo, Japan). i-Erythritol, 2,2-dimethyl-1,3-propanediol, and putrescine as test chemicals, and acetonitrile and distilled water (HPLC grade, respectively), tetrahydrofuran (stabilizer free, special grade), formic acid, K2HPO4, KH2PO4, Na2HPO4 · 12H2O, NH4Cl, MgSO4·7H2O, CaCl2, FeCl3 · 6H2O, 0.5% phosphate solution, α-D-Glucose, and 1 M sodium hydroxide were purchased from FUJIFILM Wako Pure Chemical (Osaka, Japan). Aniline as a test chemical and acetone were purchased from Kanto Chemical (Tokyo, Japan). Peptone was purchased from Showa Chemical (Tokyo, Japan). Silica gel (5 to 25 µm particle size for thin-layer chromatography) was purchased from Sigma-Aldrich (St. Louis, MO, USA). Sodium sulfite was purchased from Nacalai Tesque (Kyoto, Japan).
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7

Synthesis and Purification of TPA Stilbene

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TPA, α-phenyl-4′-[(4-methoxyphenyl)phenylamino]stilbene, shown in Fig. 1a, was obtained from Ricoh Co. Ltd. Its purity was ensured to be one spot in thin-layer chromatography. C60 (≥ 99%) and C70 (≥ 97%) were obtained from Kanto Chemical Co., Inc. The reagents o-xylene (98.0+%), tetrahydrofuran (99.5+%), acetonitrile (99.8+%), and toluene (99.5+%) were purchased from Fujifilm Wako Pure Chemical Corp. Tetramethylammonium perchlorate (≥ 99.0%), TMAP, was purchased from Nacalai Tesque, Inc.
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8

Quantifying Carotenoids and Polyphenols in Orange Juice

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Anhydrous sodium chloride (NaCl) and magnesium sulfate (MgSO4) for formulations as QuEChERS components were purchased from Fujifilm Wako Pure Chemicals (Tokyo, Japan). β-Carotene, β-cryptoxanthin, campesterol, ferulic acid, stigmasterol, sitosterol, and rutin were purchased from Fujifilm Wako Pure Chemicals. p-Coumaric acid, diosmin, hesperidin, naringin, and narirutin were purchased from Tokyo Chemical Institute (Tokyo, Japan). Pyrogallol and 2,6-di-tert-butyl-4-methylphenol (BHT) used to prevent autooxidation were purchased from Fujifilm Wako Pure Chemicals (Tokyo, Japan).
All organic solvents (acetonitrile, formic acid, tetrahydrofuran, and methanol) and ultrapure HPLC- or LC/MS-grade water were purchased from Fujifilm Wako Pure Chemicals.
Orange juice was purchased from a local market in Tokyo, Japan.
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9

Fabrication and Characterization of Polymer-Based Devices

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The materials and reagents used for the fabrication and characterization of the devices were purchased from the following commercial sources: a polyimide sheet (thickness: 130 μm) from JMT Corporation (Osaka, Japan); a positive photoresist (S-1818G) from Dow Chemical (Midland, MI, USA); bis(12-crown-4) and 2-nitrophenyloctyl ether (NPOE) from Dojindo (Kumamoto, Japan); valinomycin, dioctyl sebacate (DOS), tetrahydrofuran (THF), polyvinylpyrrolidone (PVP), polyvinyl chloride (PVC), potassium chloride (KCl), and sodium chloride (NaCl) from Wako Pure Chemical Industries (Osaka, Japan); and sodium tetraphenylborate, poly(2-hydroxyethyl methacrylate) (poly(HEMA)), and potassium tetrakis(4-chlorophenyl)borate (KTpClPB) from Sigma Aldrich (Buchs, Switzerland). Syringe needles (inner diameter: 0.9 mm, outer diameter: 1.3 mm) were purchased from Terumo (Tokyo, Japan). Solutions were prepared with Milli-Q water (Millipore, Tokyo, Japan).
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10

Synthesis and Characterization of Fluorinated Sulfonyl Compounds

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Perfluoropropyl-1,3-bissulfonylfluoride (C3F)
was purchased from Daikin Industries, Ltd. (Osaka, Japan) and used
as received. Lithium bromide was purchased from Sigma-Aldrich and
used as received. 4-Fluorobenzenesulfonyl chloride, sodium hydroxide,
potassium hydroxide, potassium carbonate, magnesium sulfate, diethyl
ether (Et2O), ethanol (EtOH), chloroform (CH3CI), dimethyl sulfoxide (DMSO), DMSO-d6, acetonitrile-d3 (MeCN-d3), anhydrous acetonitrile (MeCN), anhydrous N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone
(NMP), p-cresol, 1,4-dioxane, hexane, and tetrahydrofuran
(THF) were purchased from Wako Pure Chemical Industries, Ltd. (Osaka,
Japan) and used as received. N,N-Diisopropylethylamine (DIPEA) was also purchased from Wako Pure
Chemical Industries, Ltd., distilled with CaH2, and stored
under a nitrogen atmosphere. Anhydrous toluene was purchased from
Kanto Chemical Co. (Tokyo, Japan) and used as received. 4,4′-Bisphenol,
4,4′-dichlorodiphenyl sulfone and 1 M lithium hexamethyldisilazide
(LiHMDS) solution in THF were purchased from Tokyo Kasei Co. (Tokyo,
Japan). 4,4′-Bisphenol and 4,4′-dichlorodiphenyl sulfone
were recrystallized from 1,4-dioxane/hexane (5:2, v/v) and THF/hexane
(1:1, v/v), respectively, before use.
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