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Boranes

Boranes are a class of chemical compounds composed of boron and hydrogen atoms.
These versatile molecules have a wide range of applications in chemistry, materials science, and energy research.
Borane compounds exhibit unique structural and reactivity properties, making them valuable tools for synthetic transformations, catalysis, and the development of novel materials.
PubCompare.ai leverages advanced AI algorithms to help researchers identify the most accurate and reproducible protocols for working with boranes, enabling reliable, high-quality results in their scientific endeavors.
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Most cited protocols related to «Boranes»

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
Glycan release and labeling of Korčula and Vis IgG samples was performed essentially as described by Royle and coworkers (46 (link)). Briefly, IgG was immobilized in a block of sodium dodecyl sulfate–polyacrylamide gel and N-glycans were released by digestion with PNGase F (ProZyme, Hayward, CA). Each step was done in a 96-well microtiter plate to achieve the best throughput of sample preparation. After deglycosylation, N-glycans were labeled with 2-AB fluorescent dye. Excess of label was removed by solid-phase extraction using Whatman 3MM chromatography paper. Finally, glycans were eluted with water and stored at −20°C until usage.
Orkney and TwinsUK IgG samples were first denatured with addition of 30 μL 1.33% sodium dodecyl sulfate (w/v) (Invitrogen, Carlsbad, CA) and by incubation at 65°C for 10min. Subsequently, 10 μL of 4% Igepal-CA630 (Sigma–Aldrich, St. Louis, MO) and 1.25 mU of PNGase F (ProZyme) in 10 μL 5× phosphate-buffered saline were added to the samples. The samples were incubated overnight at 37°C for N-glycan release. The released N-glycans were labeled with 2-AB. The labeling mixture was freshly prepared by dissolving 2-AB (Sigma–Aldrich) in dimethyl sulfoxide (Sigma–Aldrich) and glacial acetic acid (Merck) mixture (85:15, v/v) to a final concentration of 48mg/mL. A volume of 25 μL of labeling mixture was added to each N-glycan sample in the 96-well plate. Also, 25 μL of freshly prepared reducing agent solution (106.96mg/mL 2-picoline borane [Sigma–Aldrich] in dimethyl sulfoxide) was added and the plate was sealed using adhesive tape. Mixing was achieved by shaking for 10min, followed by 2-hour incubation at 65°C. Samples (in a volume of 100 μL) were brought to 80% acetonitrile (ACN) (v/v) by adding 400 μL of ACN (J.T. Baker, Phillipsburg, NJ). Free label and reducing agent were removed from the samples using hydrophilic interaction chromatography–solid-phase extraction. An amount of 200 μL of 0.1g/mL suspension of microcrystalline cellulose (Merck) in water was applied to each well of a 0.45 μm GHP filter plate (Pall Corporation, Ann Arbor, MI). Solvent was removed by application of vacuum using a vacuum manifold (Millipore Corporation, Billerica, MA). All wells were prewashed using 5×200 μL water, followed by equilibration using 3×200 μL acetonitrile/water (80:20, v/v). The samples were loaded to the wells. The wells were subsequently washed seven times using 200 μL acetonitrile/water (80:20, v/v). Glycans were eluted two times with 100 μL of water and combined eluates were stored at −20°C until usage.
Publication 2013
Acetic Acid acetonitrile Boranes Chromatography Digestion Fluorescent Dyes Glycopeptidase F Hydrophilic Interactions microcrystalline cellulose Phosphates Picoline polyacrylamide gels Polysaccharides Reducing Agents Saline Solution Solid Phase Extraction Solvents Sulfate, Sodium Dodecyl Sulfoxide, Dimethyl Vacuum
1, 3-Bis (N-benzyloxycarbonyl)-spectinomycin (6.6g, 11mmol) and NH4NO3 (8.8g, 110mmol) in 100mL of 10% acetic acid-methanol were stirred to clear solution at room temperature. 2-Methylpyridine borane (0.82g, 7.7mmol) was added to the reaction mixture in one portion. The mixture was stirred for 1 h at room temperature and the solvent evaporated. The residue was dissolved into 100mL saturated NaHCO3 solution and 100mL ethyl acetate.
After separation, the organic layer was washed with brine and dried over Na2SO4. After evaporating the solvent, 2.6g (40%) title compound was purified by column chromatography (Isolera one, Biotage, HP column, 50g size, 5% methanol/acetonitrile).15 (link) 1H NMR (400 MHz, Methanol-d4) δ 7.46 – 7.19 (m, 10H), 5.30 – 4.98 (m, 4H), 4.91 (s, 1H), 4.53 (t, J = 10.5 Hz, 1H), 4.24 – 3.82 (m, 7H), 3.18 – 3.01 (m, 6H), 1.92 – 1.77 (m, 1H), 1.68–1.61 (m, 1H), 1.25 (d, J = 5.9 Hz, 3H). MS-ESI: m/z 602 (M++H).
Publication 2016
1H NMR 2-picoline Acetic Acid acetonitrile Bicarbonate, Sodium Boranes brine Chromatography ethyl acetate Methanol Solvents Spectinomycin
Glycoproteins or blood serum samples were first mixed with PBS buffer (20mM, pH 7.5) and thermally denatured in a 90 °C water bath for 20 minutes. After the denatured sample was cooled to ambient temperature, about 100 units of PNGase F was added to each sample and 2007incubation was conducted in a 37 °C water bath for 18 hours (73 (link)). After PNGase F digestion, protein was removed by precipitation using 90% ethanol. The purified glycans were then subjected to reduction using a procedure based on a method for the reductive β-elimination of O-linked oligosaccharides (74 (link)). An aqueous 10 µg/µL ammonium borane complex solution was prepared. Ten µL of ammonium borane solution was added to each sample and incubated in a 60 °C water bath for one hour. After incubation, 400 µL of methanol was added to each sample which was then dried using a centrifugal vacuum concentrator. This step was repeated 3 to 4 times until excess ammonium borane was removed. The dried reduced sample was resuspended in 1.2 µL of water, 30 µL DMSO and 20 µL of iodomethane for permethylation. A solid-phase permethylation protocol was utilized in this study (57 (link)). A spin column was pack by transferring DMSO soaked sodium hydroxide beads using a micropipette; then DMSO was forced out by centrifugation. The sample mixture was then applied to the prepared reaction spin column. After 25 minutes of incubation, 20 µL of iodomethane was added to the spin column. After another 15 minutes of incubation, the permethylated glycans were eluted using 100 µL of acetonitrile. The eluent was then dried using a centrifugal vacuum concentrator because of the existence of DMSO and a high concentration of salts. Finally, the dried sample was resuspended in a 20% acetonitrile, 0.1% formic acid solution for LC-MS/MS analysis.
Publication 2016
acetonitrile Ammonium Bath Boranes Buffers Centrifugation Digestion Ethanol formic acid Glycopeptidase F Glycoproteins Methanol methyl iodide Oligosaccharides Polysaccharides Proteins Salts Serum Sodium Hydroxide Sulfoxide, Dimethyl Tandem Mass Spectrometry Vacuum
The stereochemically pure isomers of 12 and PZM21 were synthesized from corresponding (R)- and (S)-amino acid amides, which were either commercially available or readily prepared from the corresponding acid or ester (see Supplementary Information). The primary amino group was dimethylated using an excess of aqueous formaldehyde and sodium triacetoxyborohydride in aqueous acetonitrile. The carboxamides 16a,b were converted to primary amines by treatment with borane-tetrahydrofurane complex under reflux yielding the diamines 17a,b. Henry reaction of thiophene-3-carbaldehyde with nitroethane afforded the nitropropene derivative 18, which was converted into the racemic alkylamine 19. Activation with 4-nitrophenyl chloroformate yielded the carbamates 20, which were coupled with the enantiopure primary amines 17a,b to achieve diastereomeric mixtures of the corresponding ureas 12 and 21. HPLC separation using a semi-preparative Chiralpak AS-H column gave the overall eight pure stereoisomers of 12 and 21 including PZM21.
To determine the absolute configuration of the final products and efficiently prepare PZM21, we synthesized enantiomerically enriched carbamate 20, coupled it with the corresponding primary amines. For enantiomeric enrichment, we performed chiral resolution of the racemic primary amine 19 via repetitive crystallization with di-p-anisoyl-(S)-tartaric acid. After triple crystallization, we obtained 19 enriched in dextrorotatory enantiomer ([α]D25 = + 20.5°). The corresponding (R)-acetamide has been previously characterized as dextrorotatory ([α]D20 = + 49.8°), so enantiomerically enriched 19 was treated with acetic anhydride and triethylamine, and the specific rotation of the product was measured. Based on the value of specific rotation of the resulting acetamide ([α]D21 = − 46.6°), we assigned the absolute configuration of the major isomer to be (S). (S)-enriched 20 was used for synthesis of the final urea derivatives and absolute configuration of diastereomers in pairs was assigned based on the equality of retention time in chiral HPLC. A full description of the synthetic routes and analytical data of the compounds 12, PZM21 and its analogues PZM22-29 are presented in the Supplementary Information.
Publication 2016
acetamide acetic anhydride acetonitrile Acids Amides Amines Amino Acids Anabolism Boranes Carbamates chiralpak AS Crystallization derivatives Diamines Esters Formaldehyde High-Performance Liquid Chromatographies Isomerism nitroethane Retention (Psychology) Sodium Stereoisomers tartaric acid Thiophene triethylamine Urea

Most recents protocols related to «Boranes»

All chemicals including cobalt nitrate hexahydrate (Co(NO3)2·6H2O, AR), copper nitrate trihydrate (Cu(NO3)2·3H2O, AR), sodium hypophosphite monohydrate (NaH2PO2·H2O, AR), potassium hydroxide (KOH, AR), hydrochloric acid (HCl, 37%), and ammonia borane (NH3BH3, 97%) were purchased from Shanghai Aladdin Bio-Chem Technology Co., Ltd, China. Deionized water was used throughout this experiment.
Publication 2023
Ammonia Boranes cobaltous nitrate hexahydrate Copper Hydrochloric acid Nitrates potassium hydroxide sodium hypophosphite monohydrate
For performing the photocatalytic
H2 production reaction from ammonia borane (NH3BH3), powder samples of KTLO, HTO, exf-HTO, and Sn/exf-HTO
were dispersed in 4.5 mL of distilled water in a Pyrex test tube purged
with N2 for 30 min. Before sealing with a rubber septum
properly, 0.5 mL of 40 mM NH3BH3 was added.
For the H2 evolution reaction from water, powder samples
(5 mg) were dispersed separately in 5 mL of distilled water (20%V/V
methanol) in a Pyrex test tube which was sealed properly and purged
with N2 for 30 min. The test tube was illuminated via the
solar simulator while stirring constantly. The amount of H2 produced was measured with the gas chromatograph, directly taking
injections from the headspace of the Pyrex tube using a gastight syringe.
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Publication 2023
Ammonia Biological Evolution Boranes Gas Chromatography Powder Rubber Syringes
A total of 40 mg of magnetic NHG’s (50 nm) matrix and 79 mg boric acid (1.27 mmol) were taken in a reactor. A total of 150 µL of trimethyl borate (1.27 mmol) was added followed by the addition of 4.25 mL 1 M borane-THF complex (4.25 mmol). After the cessation of hydrogen evolution, the reactor was capped tightly and kept in an oil bath at 65 °C for 96 h. The matrix was then centrifuged and washed with MeOH (20 mL × 5), DMF (20 mL × 5), and water (20 mL × 5) using magnetic susceptibility for separation. The resulting matrix was kept in 10 mL H2O.
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Publication 2023
Bath Biological Evolution Boranes boric acid Hydrogen Susceptibility, Disease trimethyl borate
The centrifuged polymeric NHG’s (160 mg) and 319 mg boric acid (5.16 mmol) was poured into a glass pressure tube. A total of 607 µL of trimethyl borate (5.16 mmol) was added followed by the addition of 17 mL 1 M borane-THF complex (17 mmol). After the cessation of hydrogen evolution, the tubes were sealed and kept in an oil bath at 65 °C for 72 h. The NHG’s were then centrifuged and washed with MeOH (10 mL × 2). The obtained precipitate was mixed with methanol (8 mL) and piperidine (2 mL), transferred to a reactor, and heated to 65°C for 20 h under pressure to destroy the borane complexes. Following the decantation of the piperidine-borane solution, water was added, and the suspension was centrifuged and washed with distilled water (10 mL × 3). The reduced NHGs were dialyzed against 25 L DDW for 2 days. The water was changed twice per day.
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Publication 2023
Bath Biological Evolution Boranes boric acid Hydrogen Methanol piperidine Polymers Pressure trimethyl borate
To obtain –OH functional end groups, the poly(butadiene) of exclusively (~100%) -1,2 microstructure is submitted to post-polymerization chemical modification reactions, namely hydroboration and oxidation. In this process, each vinyl bond (-CH=CH2 per monomeric unit) is converted to -CH2-CH2-OH, leading to the desired -OH group in all monomeric units of the PB blocks. To perform the hydroboration reaction 0.15 g (3.3 mmol, 6.6 mL) of 9-BBN were introduced into 1 g of PS-b-PB1,2-b-PDMS (sample 1, corresponding to 2.7 mmoles of the PB1,2 segment) which was dissolved in tetrahydrofuran (0.2 w/v%) under nitrogen atmosphere at −15 °C. The solution was left to warm up to ambient conditions and was stirred for 24 h to ensure the completion of the hydroboration process. Notably, the 9-BBN is used in ~20% excess compared to the mol of the PB1,2 block. Following this, the solution was placed at −25 °C, and 1 mL of properly degassed methanol was added to deactivate all the excess of the borane reagent. After 30 min, NaOH (3.1 mmoles 6 N, 10% excess compared to the borane moles) was introduced to prevent the development of crosslinked networks due to borane by-products. Following, the oxidizing agent H2O2 (6.2 mmoles 30% w/v solution, 50% excess compared to the NaOH moles) was added, and the solution was stirred at −25 °C for 2 h before being placed at 55 °C for 1 h, where the separation of the desired organic and aqueous phases occurred. The organic phase was poured into a 0.25 M NaOH solution, and subsequently, the polymer was dissolved in THF/MeOH and washed with 0.25 M NaOH twice using a Buhner funnel [28 (link),29 (link)]. Finally, the polymer was thoroughly washed with copious amounts of distilled water and placed in a vacuum oven to remove any volatile compounds. Coherent procedures were employed in all terpolymers. The chemical modification reactions for sample PB1,2-b-PS-b-PDMS or sample 3 are provided in Scheme 1c. Similar reactions are followed for the other sequence of PS-b-PB1,2-b-PDMS samples.
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Publication 2023
1,3-butadiene Atmosphere Boranes Methanol Moles Nitrogen-15 Oxidants Peroxide, Hydrogen Poly A Polymerization Polymers Polyvinyl Chloride tetrahydrofuran Vacuum

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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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Borane-ammonia complex is a stable, white, crystalline compound. It is commonly used as a reducing agent in organic synthesis. The compound consists of a borane (BH3) molecule coordinated to an ammonia (NH3) molecule, forming a stable complex.
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Formic acid is a colorless, pungent-smelling liquid chemical compound. It is the simplest carboxylic acid, with the chemical formula HCOOH. Formic acid is widely used in various industrial and laboratory applications.
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Iodomethane is a colorless, volatile organic compound used as a laboratory reagent. It has the chemical formula CH3I and is typically employed as a methylating agent in various chemical reactions and synthesis procedures.
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PNGase F is an enzyme that cleaves the bond between the asparagine residue and the N-acetylglucosamine residue in N-linked glycoproteins. It is commonly used in the analysis and characterization of glycoproteins.
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Sodium hydroxide beads are a chemical compound used in various laboratory and industrial applications. They are composed of small, solid pellets or beads of sodium hydroxide, a strong base. Sodium hydroxide beads are known for their ability to absorb and neutralize acids, making them a valuable tool for pH adjustment and control in various processes.
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Acetic acid is a colorless, vinegar-like liquid chemical compound. It is a commonly used laboratory reagent with the molecular formula CH3COOH. Acetic acid serves as a solvent, a pH adjuster, and a reactant in various chemical processes.
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Methanol is a colorless, volatile, and flammable liquid chemical compound. It is commonly used as a solvent, fuel, and feedstock in various industrial processes.
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Acetonitrile is a highly polar, aprotic organic solvent commonly used in analytical and synthetic chemistry applications. It has a low boiling point and is miscible with water and many organic solvents. Acetonitrile is a versatile solvent that can be utilized in various laboratory procedures, such as HPLC, GC, and extraction processes.
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Ammonia borane is a colorless, crystalline solid chemical compound with the formula BH3NH3. It is a hydrogen-rich material that can be used as a potential hydrogen storage medium.

More about "Boranes"

Boranes are a versatile class of chemical compounds composed of boron and hydrogen atoms.
These unique molecules have a wide range of applications in chemistry, materials science, and energy research.
BH3 compounds, also known as borane or borohydride, exhibit distinctive structural and reactivity properties, making them valuable tools for synthetic transformations, catalysis, and the development of novel materials.
Boranes can be used in a variety of applications, including as reducing agents, in the synthesis of other boron-containing compounds, and in the production of advanced materials.
Related terms include diborane (B2H6), trimethylborane (B(CH3)3), and ammonia borane (NH3BH3), which is a promising hydrogen storage material.
PubCompare.ai leverages advanced AI algorithms to help researchers identify the most accurate and reproducible protocols for working with boranes, enabling reliable, high-quality results in their scientific endeavors.
By exploring the power of AI-driven protocol comparison, researchers can discover the future of borane research and unlock new possibilities in chemistry, materials science, and beyond.
To work with boranes, researchers may utilize solvents like DMSO, formic acid, iodomethane, and acetonitrile.
Additives like PNGase F, sodium hydroxide beads, acetic acid, and methanol may also be employed, depending on the specific application.
By understanding the properties and reactivity of boranes, scientists can develop innovative solutions to complex problems and advance the field of borane research.