NHSA was synthesized according to the literature [28 (link)]. NIPAAm (Wako; >98%) was recrystallized from toluene/n-hexane. AIBN (Wako, Osaka, Japan; >98%), 1,2,3,4-tetrahydronaphthalene (tetralin; Aldrich, St. Louis, Missouri, USA; 99%), ethylenediamine (2DA; Wako; >99%), 1,4-butanediamine (4DA; Wako; >98%), 1,6-hexanediamine (6DA; Wako; >98%), 1,8-octanediamine (8DA; Wako; >98%), 1,12-dodecanediamine (12DA; Tokyo Kasei, Tokyo, Japan; >98%), IPA (Wako; >99%), BA (Wako; >98%), HEA (Tokyo Kasei; >99%), 1,4-dioxane (Wako; >99.5%), THF (Wako; >99.5%), and DMF (Wako; >99.5%) were used as received.
1 4 dioxane
Manufactured by Fujifilm
Sourced in Japan
1,4-dioxane is a cyclic ether compound used as a laboratory solvent. It has a low boiling point and is miscible with water and many organic solvents. 1,4-dioxane is commonly employed in a variety of analytical and research applications within the laboratory setting.
Automatically generated - may contain errors
Lab products found in correlation
N n dimethylformamide (dmf), by Fujifilm (3 mentions)
Methanol, by Fujifilm (3 mentions)
Acetonitrile, by Kanto Chemical (3 mentions)
Nipaam, by Fujifilm (2 mentions)
Dimethyl sulfoxide (dmso), by Fujifilm (2 mentions)
Chloroform, by Fujifilm (2 mentions)
Diethyl ether, by Fujifilm (2 mentions)
2 2 azobisisobutyronitrile aibn, by Merck Group (2 mentions)
1 4 butanediamine, by Fujifilm (1 mentions)
Ingenuity pathway analysis (ipa), by Fujifilm (1 mentions)
Polyoxyethylene sorbitan monolaurate tween 20, by Kanto Chemical (1 mentions)
Cacl2, by Fujifilm (1 mentions)
K2hpo4, by Fujifilm (1 mentions)
Cyclohexane, by Fujifilm (1 mentions)
Tween 20, by Fujifilm (1 mentions)
Tween 80, by Fujifilm (1 mentions)
Chicken egg white lysozyme l6876, by Merck Group (1 mentions)
Span 80, by Fujifilm (1 mentions)
Dnase 1, by Merck Group (1 mentions)
Nuclease p1, by Fujifilm (1 mentions)
18 protocols using 1 4 dioxane
1
Synthesis and Characterization of NHSA
2
Preparing ETFE Films with Functionalized Monomers
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A 50-μm-thick ETFE film was purchased from Asahi Glass Co., Ltd. (Osaka, Japan), and used as a substrate. Methanol and 1,4-dioxane (super dehydrated) were purchased from FUJIFILM Wako Pure Chemical Co., Ltd. (Osaka, Japan), and used as received. Polyoxyethylene sorbitan monolaurate (Tween 20) was purchased from Kanto Chemical Co., Ltd. (Tokyo, Japan); Diisopropyl phosphite, 4′-Aminobenzo-15-crown-5-ether, and a 4-aminoazobenzene hydrochloride salt were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan), and used as received. The monomer St-CHO was prepared according to previous papers [30 (link),33 (link)].
3
Biomimetic Hydroxyapatite Microrods Synthesis
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Cyclohexane, CaCl2, K2HPO4, and KOH were purchased from Wako Pure Chemical Industries and were of analytical grade. The three types of surfactants, namely, Span 80 (sorbitan monooleate), Tween 20 (polyoxyethylene (20) sorbitan monolaurate), and Tween 80 (polyoxyethylene (20) sorbitan monooleate) (a hydrophilic surfactant, HLB value: 15) [25] , were reagent grade products of Wako Pure Chemical Industries. Commercially available HA (Apatite HAP, monoclinic, Wako Pure Chemical Industries) was used as the HA microrods, for comparison. KBr for infrared (IR) analysis was purchased from Wako Pure Chemical Industries. Four proteins, namely, bovine serum albumin (A3059), bovine γ-globulin (G5009), equine skeletal muscle myoglobin (M0630), and chicken egg white lysozyme (L6876), were obtained from Sigma-Aldrich. Poly(l -lactic acid) (PLLA) was a gift from Toyota Motor Corp. The PLLA properties included the weight average molecular weight: 1.22×105 (Mw/Mn = 3.0), optical purity: 98.5%, melting point: 174.0 °C, and glass transition temperature: 59.7 °C. Analytical grade 1,4-dioxane was purchased from Wako Pure Chemical Industries. All chemicals were used without further purification.
4
Nuclease P1 and Phosphodiesterase Analysis
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1,4-Dioxane was purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan; purity >99.9%). Nuclease P1 and HPLC-grade acetonitrile were also purchased from Wako Pure Chemical Industries, Ltd. Phosphodiesterase I was purchased from Worthington Biochem (Lakewood, NJ, U.S.A.). Bovine spleen Phosphodiesterase II, DNase I, and bacterial alkaline phosphatase Type III (Escherichia coli) were purchased from Sigma-Aldrich (St. Louis, MO, U.S.A.). All other chemicals used were of analytical grade and purchased from Wako.
5
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.
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.
6
Synthesis of Cationic Thermoresponsive Polymers
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N-Isopropylacrylamide (IPAAm) and (3-acrylamidopropyl)trimethylammonium chloride (APTAC) were provided by KJ Chemicals (Tokyo, Japan). IPAAm was recrystallized from hexane, and APTAC was used as received. 3-Aminopropyltriethoxysilane (APTES) was purchased from Shin-Etsu Chemical (Tokyo, Japan). 4-Cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid (CDPA) as well as Dulbecco’s phosphate buffered saline without calcium chloride and magnesium chloride (DPBS) were obtained from Sigma-Aldrich (St. Louis, Missouri, USA). N-Hydroxysuccinimide (NHS), N,N’-dicyclohexylcarbodiimide (DCC), 4,4ʹ-azobis(4-cyanovaleric acid) (V-501), tris(2-carboxyethyl)phosphine hydrochloride (TCEP), diethyl ether, dehydrated toluene, methanol, acetone, dehydrated dichloromethane (DCM), and 1,4-dioxane were obtained from FUJIFILM Wako Pure Chemicals (Osaka, Japan) and used without further purification. Glass coverslips (24 mm × 50 mm, thickness: 0.2 mm) were purchased from Matsunami Glass (Osaka, Japan). Water used in this study was purified using a Milli-Q Synthesis A10 system (Millipore, Billerica, Massachusetts, USA).
7
Synthesis of Telechelic PEO-Based Copolymers
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S-1-Dodecyl-S’-(α,α’-dimethyl-α”-acetic acid)trithiocarbonate (CTA, purity >99%) was purchased from Trylead Corporation. Telechelic (–OH terminated) poly(ethylene oxide) (PEO), semi-telechelic PEO monomethyl ether, poly(ethylene oxide)99-b-poly(propylene oxide)69-b-poly(ethylene oxide)99 (F127), and 2,2′-azobisisobutyronitrile (AIBN) were purchased from Sigma-Aldrich. Anhydrous dichloromethane, 1,4-dioxane, and oxalyl chloride were purchased from Wako Chemicals. N-(3-Aminopropyl)methacrylamide (NAPMAm) was purchased from Polyscience. N-isopropylacrylamide (NIPAAm) was generously donated by the Kojin Corporation and purified via two times recrystallizations from a toluene/hexane (1:10 by weight) mixed solvent. AIBN was recrystallized from methanol prior to use. PEO and F127 was dried by azeotropic distillation using toluene prior to use. Bis(2,2′-bipyridine)(1-(4′-methyl-2,2′-bipyridine-4-carbonyloxy)-2,5-pyrrolidinedione)ruthenium(II) bis(hexafluorophosphate) (Ru(bpy)3-NHS) was synthesized according to the previously reported procedure29 . All other chemical reagents were from Wako Chemicals and used as received unless otherwise noted.
8
Photochromic Benzothiophene Derivative Synthesis
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1,2-Bis(2-ethyl-6-(5-methylthiophen-2-yl)-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentene (mt-fDAE, Scheme 1) was synthesized and purified as reported previously [16] . 1,4-Dioxane (Wako, infinity pure) was used as received. Before the measurements, continuous wave UV light was irradiated to the sample solution for conversion of the open-ring isomer into the closed-ring isomer. The cyclization and cycloreversion reaction yields are respectively 0.21 and < 10 -5 in 1,4-Dioxane [16] .
9
Synthesis and Purification of Monomers
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DMAAm was kindly provided by Kohjin Co., Ltd. (Tokyo, Japan), and it was purified by distillation before use. NBAAm was prepared by the reaction of acryloyl chloride with n-butylamine, and purified by distillation before use. NIPAAm (Wako, Osaka, Japan, 98%) was purified by recrystallization from toluene/n-hexane. NHSA was prepared as reported in literature [43 (link)]. BIS (Wako, 99%), EDA (Wako, 98%), azobisisobutyronitrile (AIBN; Wako, 98%), 1,2,3,4-tetrahydronaphthalene (tetralin; Aldrich, St. Louis, MI, USA, 99%), 1,4-dioxane (Wako, 99%), DMF (Wako, 99%), and methanol (Wako) were used as received.
10
Synthesis of Functionalized Cyclodextrin Derivatives
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Sodium hydride
(60%) and tetrabutylammonium
fluoride (ca. 1 mol/L in tetrahydrofuran) were purchased from Tokyo
Chemical Industry (Japan). 1,4-Dioxane was purchased from Wako Pure
Chemical Industries (Japan). These reagents were used without further
purification. TIPS-β-CD,16 (link) the TBDMS-β-CD
dimer,8 (link) and the Janus-type β-CD tube
bearing TBDMS substituents9 (link) were prepared
according to our previously reported method. 1H and 13C NMR spectra were recorded on a JEOL NMR system (400 MHz).
The following abbreviations were used for chemical shift multiplicities:
s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet.
NMR signal assignments were based on additional two-dimensional (2D)-NMR
spectroscopy (e.g., COSY and HSQC). Infrared (IR) spectra were obtained
with a Spectrum 100FT-IR spectrometer (Perkin Elmer). MALDI-TOF MS
spectra were measured by Bruker Autoflex III. MALDI-HRMS spectra were
measured by JEOL Spiral TOF/TOF JMS–S3000. Melting points were
measured with BUCHI Melting point B-545. Elemental analysis was performed
with Perkin Elmer 240C. High-performance liquid chromatography (HPLC)
was performed using a Shimadzu Prominence HPLC system equipped with
a Soft 400 ELSD detector.
(60%) and tetrabutylammonium
fluoride (ca. 1 mol/L in tetrahydrofuran) were purchased from Tokyo
Chemical Industry (Japan). 1,4-Dioxane was purchased from Wako Pure
Chemical Industries (Japan). These reagents were used without further
purification. TIPS-β-CD,16 (link) the TBDMS-β-CD
dimer,8 (link) and the Janus-type β-CD tube
bearing TBDMS substituents9 (link) were prepared
according to our previously reported method. 1H and 13C NMR spectra were recorded on a JEOL NMR system (400 MHz).
The following abbreviations were used for chemical shift multiplicities:
s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet.
NMR signal assignments were based on additional two-dimensional (2D)-NMR
spectroscopy (e.g., COSY and HSQC). Infrared (IR) spectra were obtained
with a Spectrum 100FT-IR spectrometer (Perkin Elmer). MALDI-TOF MS
spectra were measured by Bruker Autoflex III. MALDI-HRMS spectra were
measured by JEOL Spiral TOF/TOF JMS–S3000. Melting points were
measured with BUCHI Melting point B-545. Elemental analysis was performed
with Perkin Elmer 240C. High-performance liquid chromatography (HPLC)
was performed using a Shimadzu Prominence HPLC system equipped with
a Soft 400 ELSD detector.
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