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20 protocols using tetrahydrofuran thf

1

Synthesis and Characterization of Magnesium Salt

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Example 15

(1) Synthesis of a Magnesium Salt

Under argon gas atmosphere, diphenylsilanediol (8.65 g, 40 mmol) (Tokyo Chemical Industry Co., Ltd.) was dissolved in tetrahydrofuran (THF) (20 mL) (Wako Pure Chemical Industries, Ltd.), and then a THF solution of phenylmagnesium chloride (PhMgCl) (40 mL, 80 mmol) (Tokyo Chemical Industry Co., Ltd., 2 M) was added dropwise, and the solution was stirred for 1 hour. After that, powder generated by concentration and drying of the solution, was washed with diisopropyl ether (50 mL) (Wako Pure Chemical Industries, Ltd.). The powder was filtered off and dried to obtain diphenylsilanedioxy bis(magnesium chloride), (Ph2Si(OMgCl)2).

[Figure (not displayed)]

Measurement result of 1H-NMR is shown below.

1H-NMR (400 MHz, CDCl3) δ (ppm): 6.90-8.00 (m, 10H)

(2) Preparation of the Electrolytic Solution

Under argon gas atmosphere, into diphenylsilanedioxy bis(magnesium chloride) (Ph2Si(OMgCl)2) (0.83 g, 2.5 mmol), THF (20 mL) (Wako Pure Chemical Industries, Ltd.) was mixed. The mixture was heated to 50° C., and then aluminum chloride (AlCl3) (0.67 g, 5 mmol) (Wako Pure Chemical Industries, Ltd.) was added to the mixture. After maintaining the resulting mixture at 50° C. for 10 minutes, it was cooled to obtain the electrolytic solution 14, “a solution of diphenylsilanedioxy bis(magnesium chloride)-aluminum chloride/THF”.

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2

Synthesis and Characterization of Ferulic Acid Esters

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Ferulic acid (99%) and triphenyl phosphine (99%) were purchased from Sigma-Aldrich Japan Co., Ltd. p-Coumaric acid (>98.0%), sinapinic acid (>98.0%), oxalyl chloride (>98.0%), and diisopropyl azodicarboxylate (40% in toluene, ca. 1.9 mol L−1) were purchased from Tokyo Chemical Industry Co., Ltd. Methyl ricinoleate (>97.0%), acetic anhydride (>97.0%), N,N-dimethylaminopyridine (DMAP) (>99.0%), N,N′-diisopropylcarbodiimide (DIC) (>99.0%), pyridine (>99.5%, dehydrated), N,N-dimethylformamide (DMF) (>99.5%, dehydrated), sodium sulphate (Na2SO4) (>99.0%), and tetrahydrofuran (THF) (>99.5%, with stabilizer, for gel permeation chromatography (GPC) grade) were purchased from FUJIFILM Wako Pure Chemical Corporation. p-Toluenesulfonic acid monohydrate (>99.0%) and lithium hydroxide monohydrate (>99.0%) were purchased from KISHIDA CHEMICAL Co., Ltd. Toluene (>99.5%, dehydrated), dichloromethane (CH2Cl2) (>99.5%, dehydrated), and THF (>99.5%, dehydrated stabilizer free) were purchased from Kanto Chemical and purified on a Glass Contour Solvent Purification System (NIKKO HANSEN & Co., Ltd, Japan). Chloroform-d1 (99.8 atom % D with 0.03 vol% tetramethylsilane) was purchased from Kanto Chemical. These chemicals were used without further purification unless otherwise noted. 4-(Dimethylamino)pyridinium p-toluenesulfonate (DPTS) was synthesised according to the literature.43 (link)
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3

Synthesis and Purification of Organometallic Precursor

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Dichloromethane, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ethyl acetate, hexane, methanol, tetrahydrofuran (THF), lithium bromide (LiBr), and chloro(1,5-cyclooctadiene)(η5-pentamethylcyclopentadienyl)ruthenium(II) (Cp*RuCl(COD)) were purchased from FUJIFILM Wako Pure Chemical Corp. (Osaka, Japan). A solution of tetrabutylammonium fluoride (TBAF) in THF (1 M) was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Copper(I) bromide (CuBr), sodium chloride (NaCl), sodium sulfate (Na2SO4), and tetrasodium ethylenediaminetetraacetate (EDTA·4Na) were purchased from Nacalai Tesque, Inc. (Kyoto, Japan). Pentamethylcyclopentadienylbis(triphenylphosphine)ruthenium(II) chloride (Cp*RuCl(PPh3)2) was purchased from Sigma–Aldrich (St. Louis, MO, USA). Merck precoated TLC plates (Silica gel 60 F254) were used for thin layer chromatography (TLC) analysis in this work. Silica gel 60 (Nacalai Tesque, spherical, neutrality) was used for column chromatography to purify the products. THF and DMF were dried with flame-dried molecular sieves 4A. Other reagents were used without further purification. tBuAH and t-butyl 6-(t-butyldimethylsilyl)-4-hydroxy-5-hexynoate (1) were prepared according to the procedure reported previously [26 (link)].
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4

Synthesis of Metal-Doped Carbon Nitride Frameworks

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Each CTF was prepared using essentially the same method described in our previous publications.7 Briefly, 2,6-dicyanopyridine (64.5 mg, Koei Kagaku) and Ketjen Black EC600JD (64.5 mg, Lion Corp.) were mixed with ZnCl2 (6.82 g, Wako) in a glass vacuum tube and then heated to 400 °C at 3.3 °C min–1 and held at that temperature for 40 h. The resulting powder was washed with deionized water, tetrahydrofuran (THF, Wako), HCl (1 M, Wako) and aqueous ammonia (1 M, Wako). The obtained CTF was dispersed in a 10 mM aqueous solution of MCl2 (M = Co, Ni or Cu) and stirred at 80 °C for 3 h. Subsequently, the product was collected by centrifugation and thoroughly washed with deionized water to remove any unbound metal salt, followed by drying at 60 °C in a vacuum oven for 1 day.
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5

Synthesis and Characterization of EVA Copolymers

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Poly(ethylene‐co‐vinyl acetate) copolymers (abbreviated as EVA) and {(2E)‐2‐methyl‐3‐[4‐(2‐methyl‐2‐propanyl)phenyl]‐2‐propen‐1‐ylidene}malononitrile (known as DCTB) were purchased from Sigma Aldrich (St. Louis, MO, USA). Chloroform (CHCl3) used in SEC and tetrahydrofuran (THF) were from Wako Pure Chemical Industries (Osaka, Japan). The poly(methyl methacrylate) standard (Mp = 1310 g mol–1) used for the external calibration of the MALDI mass spectra was purchased from Polymer Laboratories (Church Stretton, UK).
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6

Polymeric Nanoparticles for Drug Delivery

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PLGA (50:50 ratio, Mw = 24000–38000
Da) and PEG-PLGA (average MnPEG = 2000
Da, average MnPLGA = 11500 Da) were obtained
from Sigma-Aldrich (St. Louis, MO, USA). PTX, COX, and DOX were purchased
from Tokyo Chemical Industry Ltd. (Tokyo, Japan). Acetonitrile (ACN),
dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and tetrahydrofuran
(THF) were purchased from FUJIFILM Wako Pure Chemical Corporation
(Osaka, Japan).
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7

Magnesium Alloy Cytotoxicity Evaluation

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Hydrofluoric acid (HF, 46% w/w aqueous solution), tetrahydrofuran (THF), and Eagle’s minimal essential medium (E-MEM) were purchased from Wako Pure Chemical Industries Ltd. (Osaka, Japan). Fetal bovine serum (FBS) was purchased from Cosmo Bio Co., LTD. (Tokyo, Japan). Poly(D,L-lactide) (PDLLA) and poly(ε-caprolactone) (PCL) were purchased from LACTEL Absorbable Polymers (Birmingham, AL, USA). Mg alloy ‘Original ZM10’ was developed and manufactured by Fuji Light Metal Co., Ltd. The component was analyzed with an inductively coupled plasma optical emission spectrometry (ICP-OES Agilent 720, Agilent Technologies, Santa Clara, CA, USA) as shown in Table S1.
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8

Synthesis of NHC-based Amphiphiles and Metal Complexes

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The NHC-based amphiphile (MS precursor), Pd-MS, and Au-MS were synthesized according to literature methods.5,6 (link) Ag2O was purchased from Tokyo Chemical Industry, Co., Ltd. Acetone (99.0%), dichloromethane (99.5%), methanol (99.5%), chloroform (99.0%) and tetrahydrofuran (THF) were purchased from Fujifilm Wako Pure Chemical Industries, Ltd. and were used as received.
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9

Synthesis and Characterization of Magnesium Salt

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Example 16

(1) Synthesis of a Magnesium Salt

Under argon gas atmosphere, triphenylsilanol (5.53 g, 20 mmol) (Tokyo Chemical Industry Co., Ltd.) was dissolved in tetrahydrofuran (THF) (20 mL) (Wako Pure Chemical Industries, Ltd.), and then a THF solution of phenylmagnesium bromide (PhMgBr) (10 mL, 10 mmol) (Tokyo Chemical Industry Co., Ltd., 1 M) was added dropwise, and subjected to a reaction for 1 hour. After that, to an oil component generated by concentration and drying of the solution, diisopropyl ether (40 mL) (Wako Pure Chemical Industries, Ltd.) was added to generate powder. The powder was filtered off and dried to obtain magnesium bromide triphenylsiloxide (Ph3SiOMgBr).

[Figure (not displayed)]

Measurement result of 1H-NMR is shown below.

1H-NMR (400 MHz, CDCl3) δ (ppm): 6.95-7.90 (m, 15H)

(2) Preparation of the Electrolytic Solution

Under argon gas atmosphere, into magnesium bromide triphenylsiloxide (Ph3SiOMgBr) (0.95 g), THF (10 mL) (Wako Pure Chemical Industries, Ltd.) was mixed. The mixture was heated to 50° C., and then aluminum chloride (AlCl3) (0.33 g, 2.5 mmol) (Wako Pure Chemical Industries, Ltd.) was added to the mixture. After maintaining the resulting mixture at 50° C. for 10 minutes, it was cooled and filtrated to obtain the electrolytic solution 15, “a solution of magnesium bromide triphenylsiloxide-aluminum chloride/THF”.

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10

Synthesis and Characterization of Hollow Silica Particles

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Bis(triethoxysilyl)ethane was purchased from Oakwood Products, Inc. (Estill, SC, USA) and used as received. Triethoxymethylsilane was purchased from Tokyo Chemical Industry Co., Ltd (Tokyo, Japan) and used as received. Tetrahydrofuran (THF) and ethanol (super dehydrated) was purchased from FUJIFILM Wako Pure Chemical Co., Ltd (Osaka, Japan) and used as received. 6 mol L−1 hydrochloric acid was purchased from FUJIFILM Wako Pure Chemical Co., Ltd (Osaka, Japan) and used as received without purification. Hollow silica particles with a median diameter of 18–65 μm (3M™ Glass Bubbles iM16K) were purchased from 3 M Japan Ltd (hereafter, hollow silica particles of iM16K were named as HSPs). The water was purified by a Millipore Mill-Q UV system and had a resistance of 18.2 MΩ cm and total organic carbon content of <10 ppb.
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