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Deuterated solvent

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Deuterated solvents are a class of chemical compounds that contain deuterium, an isotope of hydrogen, in place of ordinary hydrogen. These solvents are widely used in various analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy, to provide a stable and non-interfering solvent environment for samples under investigation.

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94 protocols using deuterated solvent

1

Synthesis and Characterization of Organometallic Complexes

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All reactions and manipulations were carried out under normal atmospheric conditions unless otherwise stated. GeCl2·Dioxane was purchased from Strem Chemicals. Acetylacetone was purchased from Sigma Aldrich and used as received. l-glutathione and N-acetyl cysteine were purchased from Alfa Aesar. All other solvents were of ACS grade and used as commercially available. Deuterated solvents were purchased from Cambridge Isotope Laboratories (Andover, MA). 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and 2′,7′ –dichlorofluorescin diacetate (DCF-DA), and JC-1 were purchased from Cayman Chemicals. We utilized ACS grade solvents, which were purchased from Pharmco-Aaper and used without further purification or drying. Deuterated solvents were purchased from Cambridge Isotope Laboratories and used as received. Silica gel for column chromatography (Silicycle, P/N: R10030B SiliaFlash®F60, Size: 40–63 μm, Canada) was purchased from Silicycle. Aluminum backed silica-gel plates (20 × 20 cm2) were purchased from Silicycle (TLA-R10011B-323) and utilized for analytical thin-layer chromatography (TLC). Filtrations were carried out using medium-porosity ceramic funnels. Removal of solvents in vacuo was performed using a Büchi rotary evaporator and further drying was achieved by Schlenk line at ~120 mTorr using a dynamic vacuum pump.
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2

Reagents and Solvents Synthesis Protocol

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All reagents and solvents for synthesis were obtained from Sigma- Aldrich, St. Louis, MO, USA. Triethylamine was dried by refluxing CaH2, followed by distillation and storage over 4Å molecular sieves. Deuterated solvents were acquired from Cambridge Isotope Laboratories (CIL). Purification was performed using 60 mesh standard silica from Sorbtech. 1H NMR (300 MHz) and 13C NMR (100 MHz) spectra were recorded at 25°C on Varian Mercury spectrometers. Chemical shifts (δ) are given in ppm relative to TMS as an internal standard or the respective NMR solvent. Mass spectra were recorded on Thermo Fisher Scientific Exactive Plus MS (ESI).
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3

Synthesis of OEG Bis-Urea Amphiphiles

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All used materials were commercially available and used without further purification, unless noted otherwise. Deuterated solvents were purchased from Cambridge Isotopes Laboratories. The reaction was carried out under an inert argon atmosphere, and all glassware was dried in an oven before the reaction. Oligo(ethylene glycol) (OEG300), thionyl chloride, and pyridinium p-toluenesulfonate (PPTS) were purchased from Sigma-Aldrich, and 7-hydroxycoumarin and ethyl bromoacetate were purchased from Tokyo Chemical Industry (TCI). The OEG bis-urea amphiphiles, including P8-10 OMe and M8-10 OH were synthesized as previously reported [7 (link)].
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4

Air-Sensitive Organometallic Synthesis

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All air- and moisture-sensitive reactions were performed under N2 using standard Schlenk techniques or carried out under an Ar or N2 atmosphere in a Vacuum Atmospheres glovebox equipped with a gas purification system. Unless otherwise noted, all reagents were purchased from commercial sources and used without further purification. Anhydrous NiI2 was purchased from Strem Chemicals. Solvents were of reagent-grade or better and were dried by passage through activated alumina and then stored over 4 Å molecular sieves prior to use. Deuterated solvents were purchased from Cambridge Isotope Laboratories and stored over 4 Å molecular sieves. [PhTttBu]Tl,37 (link) Ti(phenSQ),38 and Tl(3,5-DBSQ)38 were prepared following published procedures.
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5

Synthesis of Multidentate Metal Complexes

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All chemicals and solvents were purchased from Sigma-Aldrich and used without further purification unless otherwise noted. All deuterated solvents were bought from Cambridge Isotopes. Diethyl ether (ether) and methanol (MeOH) were bought from Fisher. Methylene chloride (CH2Cl2) was purchased from Mallinckrodt Baker. 1,8-Bis(2,5-dihydroxybenzyl)-1,4,8,11-tetraazacyclotetradecane (H4qp4), [MnII(H3qp4)](OTf), and [FeII(H3qp4)](OTf) were synthesized and purified as previously described.15,16 (link)
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6

Synthesis of Ruthenium Benzene Complex

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Unless otherwise indicated, all
chemicals were used as received. Common solvents and reagents were
purchased from Acros, Fisher Scientific, VWR, or TCI America. Deuterated
solvents were obtained from Cambridge Isotope Laboratories. 4-Picoline,
2-picoline, 3-picoline, 3,5-lutidine, C6H6,
Et3SiH, CDCl3 and C6D6, and CD3CN were degassed and dried over 3 Å sieves.
Pyridine and quinoline were dried over CaH2 (room temperature,
overnight), vacuum-distilled, and stored over 3 Å sieves. All
glassware were heated to 120 °C before being brought into the
glovebox. 3,4,7,8-Tetramethylphenanthroline (Me4Phen) was
purchased from Acros and used as received. [cis-{(η5-C5H3)2(CMe2)2}Ru2(μ-η66-C10H8)][OTf]2 was prepared as previously
described.26 (link)
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7

Comprehensive Metabolomics Sample Preparation

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LC-MS grade acetonitrile (ACN), methanol (MeOH), and isopropyl alcohol (IPA), triethylamine, ammonium acetate, acetic acid, and N,O-bis(trimethylsilyl)trifluoroacetamide with 1% trimethylchlorosilane (BSTFA/TMCS) were purchased from FisherScientific (Pittsburgh, PA). All deuterated solvents were purchased from Cambridge Isotopes (Andover, MA). All standards were purchased from Sigma-Aldrich (St. Louis, MO). Human pooled plasma (from both males and females) was purchased from Interstate Blood Bank, INC (Memphis, TN)
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8

Synthetic Procedures for Amide-Containing Compounds

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All reagents for synthesis were from Sigma-Aldrich (St. Louis, MO). HPLC-grade or better solvents were from Fisher Scientific (Fair Lawn, NY). Deuterated solvents were from Cambridge Isotope Laboratories (Andover, MA).
Test compounds were synthesized using established procedures for amide bond formation. Compounds 3, 7 and 8 were prepared by treating tyramine[5 (link)], 3-O-methyldopamine[6 (link)] and dopamine[6 (link)] and with acetic anhydride, respectively; compounds 5, 12, and 26 were prepared by treating amine with 2-methyl-6-nitrobenzoic acid anhydride. Nicotinyl dopamine (10), feruloyl tyramine (6) and feruloyl dopamine (11) were synthesized by coupling the amine and the corresponding acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide as the coupling agent, as described previously[4 (link)]. All other amides were synthesized by treating the amine with an appropriate acyl chloride under Schotten-Baumann conditions[7 (link)]. Chemical structures of tested compounds are shown in Table 1.
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9

Synthetic Procedures and Analytical Characterization

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Reagents were purchased from Sigma-Aldrich, Tokyo Chemical Industry (TCI), and/or Cayman Chemical Company and used directly as received. Deuterated solvents were purchased from Cambridge Isotope Laboratories and used as received. 1H and 13C{1H} NMR spectra were recorded on a Bruker 500 or 600 MHz instrument. Chemical shifts are reported relative to residual protic solvent resonances. Silica gel (SiliaFlash F60, Silicycle, 230-400 mesh) was used for column chromatography. All air-free manipulations were performed under an inert atmosphere using standard Schlenk technique or an Innovative Atmospheres N2-filled glove box. UV-Vis spectra were acquired on an Agilent Cary 60 UV-Vis spectrophotometer equipped with a Quantum Northwest TC-1 temperature controller at 25 °C ± 0.05 °C.
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10

Air-Sensitive Organometallic Synthesis

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All manipulations were carried out using standard Schlenk or glovebox techniques under an atmosphere of N2. Solvents were dried and degassed by passing through a column of activated alumina and sparging with Ar gas. Deuterated solvents were purchased from Cambridge Isotope Laboratories, Inc., degassed, and stored over activated 3 Å molecular sieves prior to use. All other reagents and starting materials were purchased from commercial vendors and used without further purification unless otherwise noted. N2CPh2 was synthesized and purified by crystallization from cold pentane.14 (link) 18-Crown-6 was dried according to reported procedures prior to use.15 The [i-PrNDI]Ni2(C6H6) complex 1 was prepared according to previously reported procedures.5 (link) Elemental analyses were performed by Midwest Microlab (Indianapolis, IN).
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