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Sodium hydride

Sodium hydride (NaH) is a highly reactive chemical compound consisting of sodium and hydrogen.
It is commonly used as a strong reducing agent and a base in organic synthesis reactions.
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Most cited protocols related to «Sodium hydride»

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Publication 2008
1H NMR Acids Anabolism Carbon disulfide Chromatography Disulfides ethanethiol ethyl acetate Ethyl Ether Filtration Hexanes Iodine Polymerization Silica Gel Sodium sodium hydride sodium sulfate sodium thiosulfate Solvents trithiocarbonate
2-Iodobenzonitrile, ethyl-1H-indole-carboxylate and 5-bromo-ethyl-1H-indole-carboxylate were purchased from ABCR. Borane solution (1M in THF), absolute DMF, dimethylaminopyridine, di-tert-butyl-dicarbonate, absolute acetonitrile, palladium(II) acetate, sodium bicarbonate, basic aluminuim oxide, 2-acetylpyridine and 2-formylpyridine were bought from Fisher/Acros Organics. Ethoxy-methylchloride was obtained form TCI. Sodium hydride, phosphorus(V) sulfide, celite, hydrazine monohydrate and methyl iodide were purchased from Sigma Aldrich, while lithium hydroxide monohydrate and triphenylphosphine were from Alfa Aesar. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide-hydrochloride was purchased from IRIS biotech. Silver(I) carbonate was purchased from Merck. 2-Iodobenzylamine was prepared by a known method.26 (link) The unsubstituted indolo[2,3-d]benzazepinone (A) was prepared by following published protocols.18 (link)–20 The 11-bromo-substituted B was prepared using reported precedures,18 (link)–20 with some modifications, a detailed description of the synthesis of B is given in the Supplementary Information file.
Publication 2019
2-acetylpyridine Acetate acetonitrile Anabolism Bicarbonate, Sodium bis(tert-butoxycarbonyl)oxide Boranes Carbodiimides Carbonates Celite hydrazine hydrate indole Iris Plant lithium hydroxide monohydrate Methyl Chloride methyl iodide Oxides Palladium Phosphorus Silver sodium hydride Sulfides triphenylphosphine
Chemicals. Sodium arsenite, sodium salt (99% pure), was purchased from Sigma-Aldrich (St. Louis, MO). Ultrapure phosphoric acid was obtained from J.T. Baker (Phillipsburg, NJ). Sodium arsenate (iAsV), sodium salt (96%; Sigma-Aldrich); methylarsonate (MAsV), disodium salt (98%; Chem Service, West Chester, PA); and dimethylarsinic acid (DMAsV; 98%; Strem Chemicals, Inc., Newburyport, MA) were used as standards for speciation analysis of As in mouse tissues. All other chemicals were of the highest grade commercially available.
Mice. Four-week-old male weanling C57BL/6 mice were obtained from the Jackson Laboratory (Bar Harbor, ME) and housed in the University of North Carolina–Chapel Hill (UNC-CH) Animal Facility, which is fully accredited by the American Association for Accreditation of Laboratory Animal Care. Mice were housed five per cage in polycarbonate cages with corncob bedding in controlled conditions (12-hr light/dark cycle, 22 ± 1°C, and 50 ± 10% humidity). Mice were fed a low-fat diet (LFD; 11% fat) or a high-fat diet (HFD; 58% fat; both from Research Diets, Inc., Brunswick, NJ) and drank either diH2O or diH2O plus iAsIII (25 or 50 ppm As). Water containing iAsIII was freshly prepared every 3–4 days to minimize oxidation of iAsIII to iAsV. Water and food consumption and body mass were monitored in all exposure groups every week. Body composition was measured biweekly at the UNC-CH Nutrition Obesity Research Core, using EchoMRI-100 (EchoMRI, Houston, TX). The animals were treated humanely and with regard for alleviation of suffering. All procedures involving mice were approved by the UNC-CH Institutional Animal Care and Use Committee.
Oral glucose tolerance test (OGTT) and analyses of blood glucose and insulin. After 20 weeks, both control and iAs-treated LFD and HFD mice were fasted overnight before administration of OGTT. d-Glucose (Sigma) was dissolved in diH2O and orally administered to the fasted mice (2 g/kg of body weight) using a 20-gauge stainless steel gavage feeding needle (Fisher Scientific, Waltham, MA). Samples of whole blood (2–3 μL each) were collected from a tail-clip bleed immediately before and 15, 30, 60, 90, and 120 min after glucose administration. Blood glucose levels were measured using a Freestyle Glucose Monitoring System (Abbott Laboratories, Abbott Park, IL). Additional samples of whole venous blood (100 μL) were collected from tails immediately before and 15 min after glucose administration for determination of serum insulin levels. The blood was allowed to clot on ice for 15 min and then centrifuged (200 × g) at 4°C for 10 min.
Serum was analyzed using the Rat/Mouse Insulin ELISA kit according to the manufacturer’s protocol (Millipore, Billerica, MA). We used the FBG and FSI concentrations to calculate the homeostasis model assessment–insulin resistance (HOMA-IR) value:
HOMA-IR = 
[FSI (in microunits per milliliter) 
× FBG (in millimoles per liter)] 
÷ 22.5.
The blood glucose and serum insulin levels recorded during OGTT were used to evaluate glucose tolerance and insulin response to glucose challenge, respectively. After OGTT, mice were returned to their cages and treatment continued for 7–10 days before necropsy.
Blood and tissue collection at necropsy. Whole blood samples were collected by submandibular bleeds, and mice were sacrificed by cervical dislocation. Hematocrit (a marker of dehydration) was determined in samples of fresh blood (~ 100 μL) using 40-mm heparin-coated capillary tubes. Capillary tubes were centrifuged at 12,000 rpm in a microhematocrit centrifuge (Unico, Dayton NJ) for 15 min, and the percentage of red blood cells was recorded for each mouse. Serum was isolated from submandibular blood as described above. Liver, inguinal adipose tissue, quadriceps, and pancreas were collected during necropsy and snap frozen in liquid nitrogen. Serum and the tissue samples were stored at –80°C until analysis.
Analyses of hepatic and serum triacylglycerol. We measured triacylglycerol (TAG) contents in serum and in liver homogenates spectrophotometrically (at 490 nm) after a two-step extraction in a chloroform/methanol (2:1) mixture and in pure chloroform, using a Stanbio Enzymatic Triglyceride Kit (Stanbio, Boerne, TX), following the manufacturer’s instructions.
Speciation analysis of As in tissues. For analysis of iAs metabolites, 10% (wt/vol) tissue homogenates were prepared in diH2O and digested in ultrapure phosphoric acid. Concentrations of As species were determined in digested homogenates by hydride generation–cryotrapping–atomic absorption spectrometry (HG-CT-AAS), following previously described procedures (Hernández-Zavala et al. 2008 (link)). This method detects and quantifies total iAs (iAsIII + iAsV), total MAs (MAsIII + MAsV), and total DMAs (DMAsIII + DMAsV).
Statistical analysis. Results of the analyses are expressed as mean ± SE for each treatment group (n = 6–10). Effects of diet and iAs exposure, as well as interactions between diet and iAs exposure, were analyzed by analysis of covariance. Differences between the treatment groups were evaluated by one-way analysis of variance with Tukey or Bonferroni multiple-comparison posttests. All statistical analyses were performed using Graphpad Prism (version 5.0; GraphPad Software, San Diego, CA). Differences among means with p < 0.05 were considered statistically significant.
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Publication 2011
Thiol-terminated four-armed poly(ethylene glycol) PEG4SH was prepared in a manner similar to Goessl et al.,(6 (link)) but with some significant modifications. Five grams of hydroxy-terminated, four-armed PEG (MW 10 000) (Jenkem) was dissolved in 70 mL of toluene in a round-bottomed flask and refluxed at 80 °C. Sodium hydride (Sigma-Aldrich), 1.5 mol equiv with respect to hydroxyls, was added to the solution. Allyl bromide (Sigma-Aldrich), 1.5 mol equiv relative to hydroxyls, was diluted with 10 mL of toluene and added dropwise to the solution via an addition funnel. The reaction was refluxed overnight at 80 °C.
Any unreacted sodium hydride was neutralized with the addition of 1 mL of methanol, whereupon sodium salts were removed via filtration, and the PEG was recovered from solution by precipitation in cold diethyl ether. The PEG tetraallyl ether was dried in vacuo and then redissolved in 50 mL of methanol in a 100 mL round-bottom flask, to which was added 0.10 g of the radical photoinitiator 2,2-dimethoxy-1,2-diphenylethan-1-one (trade name Irgacure 651, BASF). Thiol acetic acid (Sigma-Aldrich), 1.5 equiv relative to the allyl groups, was added, and the solution was stirred vigorously under exposure to 10 mW/cm2 365 nm UV light for 20 min. PEG thioacetate was recovered from solution by precipitation and dried as before. Dried PEG thioacetate was dissolved in 20 mL of deionized water (diH2O), whereupon 20 mL of 2 M NaOH was added and the solution was stirred for 5 min, and 11 mL of 4 N HCl solution was added to acidify the solution and discourage disulfide formation. The aqueous solution was extracted with equivalent volumes of chloroform twice, combined fractions were concentrated by rotary evaporation, and product was recovered by precipitation in cold diethyl ether. Substitution was determined to be ∼90% by both Ellman’s analysis and proton NMR. The initiator LAP was synthesized as described previously.(20 (link))
Publication 2011
Acetic Acid allyl bromide Arm, Upper Chloroform Cold Temperature Disulfides Ethyl Ether Filtration Hydroxyl Radical Methanol Polyethylene Glycols Protons Salts Sodium sodium hydride Sulfhydryl Compounds Toluene Ultraviolet Rays
Reactions were monitored through thin-layer
chromatography (TLC) with commercial silica gel plates (Merck silica
gel, 60 F254). Visualization of the developed plates was performed
under UV lights at 254 nm and by staining with cerium ammonium molybdate,
2,4-dinitrophenylhydrazine and vanillin stains. Flash column chromatography
was performed on silica gel 60 (40–63 μm) as stationary
phase. Preparative TLCs were conducted on PLC silica gel 60 F254,
1 mm.1H NMR spectra were recorded at 300 MHz, 13C NMR spectra were recorded at 75 MHz and 19F spectrum
was recorded at 282 MHz in a 300 MHz Varian Mercury spectrometer,
using CDCl3 as solvent. Chemical shifts (δ) are reported
in ppm referenced to the CDCl3 residual peak (δ 7.26) or TMS
peak (δ 0.00) for 1H NMR and to CDCl3
77.16) for 13C NMR. The following abbreviations were used
to describe peak splitting patterns: s = singlet, d = doublet, t =
triplet, m = multiplet. Coupling constants, J, were
reported in Hertz (Hz). High-resolution mass spectra were recorded
on a Waters ESI-TOF MS spectrometer. Tetrahydrofuran (THF) was dried
by distillation under argon with sodium metal and benzophenone as
indicator. Dichloromethane (DCM) was dried by distillation under argon
with calcium hydride. Isotope labeled oxygen-18 (99% isotopic purity)
was purchased from Sigma-Aldrich (CAS Number 32767–18–3).
A small balloon was filled with oxygen-18 and used directly in the
oxidation reaction.
Publication 2018
1H NMR ammonium molybdate Argon benzophenone Calcium, Dietary Carbon-13 Magnetic Resonance Spectroscopy Cerium dinitrophenylhydrazine Distillation Isotopes Mass Spectrometry Mercury Metals Methylene Chloride Oxygen-18 Silica Gel Sodium Solvents Staining tetrahydrofuran Triplets Ultraviolet Rays vanillin

Most recents protocols related to «Sodium hydride»

To a stirred solution of the ureido-based
compounds 4, 32–35 (1.0 equiv) in dry dimethylformamide
or dichloromethane under an inert atmosphere, sodium hydride 60% dispersion
in mineral oil (2.5 equiv) was added at 0 °C. After 30 min, a
solution of 38 (1.0 equiv) in dry dimethylformamide (2.50
mL) was added dropwise. The reaction mixture was stirred for 18 h
at room temperature. The sodium hydride was quenched with water, and
the residue was reconstituted with ethyl acetate (15 mL) and water
(15 mL). The organic layer was washed with water (3 × 15 mL),
dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel
column chromatography.
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Publication 2024
Not available on PMC !
All the reactions were carried out under an argon atmosphere (5.0) employing standard Schlenk techniques. Tetrahydrofuran and N,N-dimethylformamide were puried by distillation from sodium/benzophenone and calcium hydride, respectively. For the electrochemistry experiments, HPLC grade dichloromethane was puried by distillation from calcium hydride. For the column chromatography, alumina with a particle size of 90 mm (Standard, Merck KGaA) and silica with a particle size of 40-60 mm (230-400 mesh (ASTM), Fa. Macherey-Nagel) were used.
Publication 2024
JNJ-31020028 1 was commercially obtained from InvivoChem LLC (Libertyville, IL, USA). N,N-Dimethylformamide, 99.8%, Extra Dry was purchased from Fisher Scientific (Porto Salvo, Portugal). Sodium hydride, 57–63% oil dispersion, was purchased from Enzymatic (Santo Antão do Tojal, Portugal). Sodium hydroxide and iodomethane were purchased from Merck (Lisboa, Portugal). Air- and moisture-sensitive reagents or solutions were handled under nitrogen or argon atmosphere in a vacuum system using Schlenk techniques [31 ]. All the glassware was dried by heating. The solvents, such as dichloromethane and ethyl acetate, were purified by simple distillation.
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Publication 2024
The sample of (cyanomethylene)cyclopropane
(5) used in this work was prepared by the Wittig reaction
of 1-ethoxycyclopropanol and (cyanomethyl)triphenyl-phosphonium chloride,
as described previously.1 (link),3 (link) The synthesis of 1-cyano-2-methylenecyclopropane
(7) followed the synthetic methodology that was first
developed for the synthesis of hypoglycin A, a natural product found
in unripe fruit from the Ackee tree.42 (link) Carbon
et al. synthesized ethyl methylenecyclopropanecarboxylate by adding
ethyl diazoacetate to 2-bromopropene in the presence of a copper–bronze
catalyst followed by a sodium hydride-induced elimination (Scheme 2a).43 (link),44 (link) Black and Landor utilized a zinc–copper-catalyzed reaction
to generate the methylenecyclopropane moiety in a much higher yield
(Scheme 2b).45 (link) More recently, Lai and Liu improved the yield
of the ethyl diazoacetate route by utilizing a rhodium acetate catalyst
(Scheme 2c).46 (link) Our synthesis of 7 closely follows
the established route of Lai and Liu.
Our synthesis of 1-cyano-2-methylenecyclopropane (7)
is presented in Scheme 3.47 The sequence begins with a
rhodium acetate-catalyzed cyclopropanation reaction of 2-bromopropene
with ethyl diazoacetate using a procedure modified from Scott et al.,48 (link) followed by a sodium hydride-induced elimination
of bromide from 9 to generate the methylenecyclopropane
moiety. Ester 10 is converted to amide 11(49 (link)) and then treated with phosphoric anhydride
to produce nitrile 7 through dehydration of 11.
Publication 2024
The sample of (cyanomethylene)cyclopropane
(5) used in this work was prepared by the Wittig reaction
of 1-ethoxycyclopropanol and (cyanomethyl)triphenyl-phosphonium chloride,
as described previously.1 (link),3 (link) The synthesis of 1-cyano-2-methylenecyclopropane
(7) followed the synthetic methodology that was first
developed for the synthesis of hypoglycin A, a natural product found
in unripe fruit from the Ackee tree.42 (link) Carbon
et al. synthesized ethyl methylenecyclopropanecarboxylate by adding
ethyl diazoacetate to 2-bromopropene in the presence of a copper–bronze
catalyst followed by a sodium hydride-induced elimination (Scheme 2a).43 (link),44 (link) Black and Landor utilized a zinc–copper-catalyzed reaction
to generate the methylenecyclopropane moiety in a much higher yield
(Scheme 2b).45 (link) More recently, Lai and Liu improved the yield
of the ethyl diazoacetate route by utilizing a rhodium acetate catalyst
(Scheme 2c).46 (link) Our synthesis of 7 closely follows
the established route of Lai and Liu.
Our synthesis of 1-cyano-2-methylenecyclopropane (7)
is presented in Scheme 3.47 The sequence begins with a
rhodium acetate-catalyzed cyclopropanation reaction of 2-bromopropene
with ethyl diazoacetate using a procedure modified from Scott et al.,48 (link) followed by a sodium hydride-induced elimination
of bromide from 9 to generate the methylenecyclopropane
moiety. Ester 10 is converted to amide 11(49 (link)) and then treated with phosphoric anhydride
to produce nitrile 7 through dehydration of 11.
Publication 2024

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Sodium hydride is a chemical compound with the chemical formula NaH. It is a white, crystalline solid that is commonly used as a strong reducing agent and a base in organic synthesis reactions. Sodium hydride reacts violently with water, producing hydrogen gas, and must be handled with caution.
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Triethylamine is a clear, colorless liquid used as a laboratory reagent. It is a tertiary amine with the chemical formula (CH3CH2)3N. Triethylamine serves as a base and is commonly employed in organic synthesis reactions.
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Calcium hydride is a chemical compound with the formula CaH2. It is a gray or white crystalline solid that is used as a desiccant and reducing agent in various industrial and laboratory applications.
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Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.
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Methanol is a clear, colorless, and flammable liquid that is widely used in various industrial and laboratory applications. It serves as a solvent, fuel, and chemical intermediate. Methanol has a simple chemical formula of CH3OH and a boiling point of 64.7°C. It is a versatile compound that is widely used in the production of other chemicals, as well as in the fuel industry.
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Tetrahydrofuran is a colorless, volatile, and flammable organic compound. It is commonly used as a polar aprotic solvent in various industrial and laboratory applications. Tetrahydrofuran's core function is to serve as a versatile solvent for a wide range of organic compounds, including polymers, resins, and other materials.
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N,N-dimethylformamide is a clear, colorless liquid organic compound with the chemical formula (CH3)2NC(O)H. It is a common laboratory solvent used in various chemical reactions and processes.
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4-dimethylaminopyridine is a chemical compound used as a laboratory reagent. It serves as a nucleophilic catalyst in various organic reactions. The compound is widely utilized in the synthesis of organic compounds and pharmaceutical intermediates.
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Toluene is a colorless, flammable liquid with a distinctive aromatic odor. It is a common organic solvent used in various industrial and laboratory applications. Toluene has a chemical formula of C6H5CH3 and is derived from the distillation of petroleum.

More about "Sodium hydride"

Sodium hydride (NaH), a highly reactive chemical compound composed of sodium and hydrogen, is a widely used reducing agent and base in organic synthesis reactions.
This versatile reagent finds applications in a variety of laboratory and industrial settings, from pharmaceutical development to materials science.
Closely related compounds include triethylamine (Et3N), a common organic base, and calcium hydride (CaH2), another potent reducing agent.
Solvents such as acetonitrile (MeCN), methanol (MeOH), and tetrahydrofuran (THF) are often employed in reactions involving sodium hydride, while hydrochloric acid (HCl) and N,N-dimethylformamide (DMF) may be used for workup or purification steps.
The organic catalyst 4-dimethylaminopyridine (DMAP) can also play a role in facilitating certain sodium hydride-mediated transformations, while toluene is a common reaction medium.
Optimizing sodium hydride research can be a challenge, but PubCompare.ai offers a powerful AI-driven platform to streamline your workflow.
By accessing a vast database of literature, preprints, and patents, you can identify the most reliable and effective protocols, enhancing the quality and efficiency of your experiments.
Experince the power of PubCompare.ai today and maximaze your sodium hydride research potentiel.