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Bromosuccinimide

Bromosuccinimide is a versatile reagent used in organic synthesis for a variety of transformations, including halogenation, oxidation, and electrophilic substitution reactions.
It is a mild, selective, and efficient brominating agent that can be used to introduce bromine atoms into a wide range of organic compounds.
Bromosuccinimide is particularly useful in the synthesis of complex molecules, medicinal and pharmaceutical compounds, and natural products.
It is an important tool in the chemist's toolkit, enabling the efficient and selective functionalization of organic substrates.
Researchers can optimzie their Bromosuccinimide protocols using PubCompare.ai's AI-driven tools for literature search, protocol comparisons, and product identification, ensuring reproducible and accurate results in their chemical transformations.

Most cited protocols related to «Bromosuccinimide»

Avicel PH 101, aniline, 4‐pentylaniline, 4‐octylaniline, 4‐[(N‐Boc)aminomethyl]aniline, 4‐trifluoromethyl aniline, anhydrous LiCl, and anhydrous N,N‐dimethylacetamide were obtained from Sigma–Aldrich (St. Louis, MO, USA). ortho‐Dichlorobenzene, tert‐butyl nitrite (isoamyl nitrite), 1,4‐dioxane, 4‐ethylaniline, 4‐ethynylaniline, l‐ascorbic acid, N,N‐dimethylformamide, trimethylsilyl azide, ethylenediaminetetraacetic acid, N‐bromosuccinimide, triphenylphosphine, propionic anhydride, sodium azide, and tetrabutylammonium hexafluorophosphate were supplied by Tokyo Chemicals Industry Co., Ltd. (Tokyo, Japan). Acetonitrile and hydrochloric acid were purchased from Naclai Tesque, Inc. (Kyoto, Japan). All other chemicals were from Kanto Chemical (Tokyo, Japan).
Carbon fiber T700SC‐12000‐50C was provided by Toray Industries (Tokyo, Japan) with the following specifications: diameter, 7 μm; tensile strength, 4900 MPa; sizing agent, 1 % of the total mass. The fibers were cleaned before the experiments to remove the sizing agent and impurities from the surface according to our previous report.25 The cleaning procedure included ultrasonic washing in acetone (2×) for 20 min at 40 °C, followed by rinsing with methanol and water, and ending with drying in a vacuum oven (ADP 200, Yamato Scientific Co., Ltd, Tokyo, Japan) at 150 °C for 3 h. The carbon fibers were stored in sealed vials, and before use, they were cleaned in an ultrasonic bath with acetone (5×) for 10 min; the solvent was changed after each step. The removal of the sizing agent was confirmed by TGA, XPS, and AFM measurements in our previous study.25Cellulose propionate (Mw≈200000 g mol−1) was supplied by Scientific Polymer Products, Inc. (Ontario, NY, USA) and was used as received for the matrix of the composite. The degree of substitution (DS) value was determined to be 2.76 by using the benzoylation method according to a previous study.36
Publication 2018
4-ethylaniline 4-trifluoromethylaniline Acetone acetonitrile aniline Ascorbic Acid Avicel PH-101 azidotrimethylsilane Bath Bromosuccinimide Carbon Fiber dimethylacetamide Dimethylformamide dioxane Edetic Acid Hydrochloric acid isoamyl nitrite Methanol n-butyl nitrite Polymers Propionate propionic anhydride Sodium Azide Solvents TERT protein, human tetrabutylammonium triphenylphosphine Ultrasonics Vacuum
The synthesis of the compounds started with the functionalization of commercial bromopyrazin-2-amine either with a bromine or iodine atom. A subsequent reaction of the resulting para-substituted aminopyrazines Br-Clm-9 or Br-Clm-11 with N-bromosuccinimide in ethanol provided the homo-(Br-Clm-10) or the hetero-dihalogenated products, respectively. Coelenteramines Br-Clm-1/3/5/7/8 were obtained after the Suzuki–Miyaura cross-coupling of the corresponding functionalized aminopyrazines with commercial boronic acids using bis(triphenylphosphine)palladium (II) dichloride as the palladium source and potassium carbonate as the base. Compounds Br-Clm-2, Br-Clm-4, and Br-Clm-6 were obtained after halogenation of Coelenteramines Br-Clm-1, Br-Clm-3, and Br-Clm-5 in standard conditions, respectively. Synthetic Coelenteramide Br-Clmd was synthesized through N-acetylation of Br-Clm using pyridine as the base to avoid the formation of the disubstituted subproduct. Precursors of the initial Coelenterazine derivatives Br-Cla-1/2/3, OH-Cla, and Br-Clm-1 were synthesized from pyrazin-2-amine in a similar manner, following the procedures described in [12 (link),13 (link),14 (link)]. Then, the imidazopyrazinone core was formed after condensation of the corresponding Coelenteramines with a 1,2-dicarbonylic fragment (methyl glyoxal) [12 (link),13 (link),14 (link)]. This route has been repeatedly used as the main synthetic path for the obtention of Coelenterazine analogs and derivatives since it goes through stable intermediates, provides the desired compounds in high yields, and is compatible with a great variety of functional groups. The structural characterization was performed using 1H- and 13C-NMR spectroscopy as well as FT-MS spectrometry. Br-Cla-1/2/3, OH-Cla, and Br-Clm-1/3 have already been described in the literature [12 (link),13 (link),14 (link)], Br-Clm-9 and Br-Clm-10 are commercially available, and further details for the compounds Br-Clmd and Br-Clm-1/2/4/5/6/7/8/11 can be found in the Supplementary Materials.
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Publication 2022
Acetylation Amines Boronic Acids Bromine Bromosuccinimide Carbon-13 Magnetic Resonance Spectroscopy coelenteramide coelenterazine derivatives Ethanol Halogenation Homo Iodine Palladium palladium chloride potassium carbonate pyridine Pyruvaldehyde Spectrometry Spectroscopy, Nuclear Magnetic Resonance Spectrum Analysis triphenylphosphine
A 4-step synthetic strategy was developed for the preparation of the chloride precursor and LW223 (Supplemental Fig. 1; supplemental materials are available at http://jnm.snmjournals.org). Initially, the starting material, 3-methyl-4-phenylquinoline-2-carboxylic acid, was prepared as previously reported by us (14 (link)). This was converted to the (R)-sec-butylamide by coupling with (R)-sec-butylamine using the coupling agent hexafluorophosphate benzotriazole tetramethyl uronium. Under standard basic conditions, the amide was subjected to an N-methylation. The key step then involved a radical-mediated bromination of the 3-methyl substituent using N-bromosuccinimide and the radical initiator benzoyl peroxide. The resulting bromide intermediate was then converted to the chloride or LW223 using lithium chloride or sodium fluoride, respectively. All intermediates and final compounds were purified by column chromatography and characterized using a combination of nuclear magnetic resonance spectroscopy and mass spectrometry (organic chemistry section within supplemental materials (14 (link),15 (link))). The 2 amide rotamers of LW223 were separated and characterized by liquid chromatography–mass spectrometry (Supplemental Fig. 2).
18F-LW223 was prepared as shown in Figure 1, using the GE Healthcare TRACERlab FXFN synthesizer. The radiotracer was purified by semipreparative high-performance liquid chromatography using the following conditions: C18 Synergi Hydro-RP 80 Å, 150 × 10 mm, 4-μm column (Phenomenex), acetonitrile/water (70:30 v/v), and flow rate of 3 mL/min. 18F-LW223 was formulated in 10% ethanol in saline. The average radioactivity yield was 50% ± 4% (starting from 22 ± 3 GBq of 18F-fluoride, n = 34) after a total synthesis time of 55 min. The identity of 18F-LW223, radiochemical purity (>99%), and molar activity (89 ± 12 GBq/μmol, n = 34) were determined by high-performance liquid chromatography analysis at the end of synthesis.
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Publication 2021
acetonitrile Amides Anabolism benzotriazole Bromides Bromination Bromosuccinimide Carboxylic Acids Chloride, Lithium Chlorides Chromatography Ethanol Fluorides High-Performance Liquid Chromatographies Liquid Chromatography Mass Spectrometry Methylation methyl radical Molar Peroxide, Benzoyl Radioactivity Radiopharmaceuticals Saline Solution Sodium Fluoride Spectroscopy, Nuclear Magnetic Resonance
Labeling kinetics of HaloTag7 and HaloTag9 with TMR-CA were measured by recording fluorescence anisotropy changes over time using a BioLogic SFM-400 stopped-flow instrument (BioLogic Science Instruments) in single mixing configuration at 37 °C. Monochromator wavelengths for excitation was set to 555 nm and a 570-nm long pass filter was used for detection. Protein and substrates were mixed in a 1:1 stoichiometry in activity buffer supplemented with 0.5 mg ml−1 BSA. Concentrations were varied from 0.125 µM to 0.5 µM. The anisotropy of the free substrate was measured to obtain a baseline. The dead time of the instrument was measured according to the manufacturer’s protocol (BioLogic Technical note no. 53) by recording the fluorescence decay during the pseudo first-order reaction of N-acetyl-l-tryptophanamide with a large excess of N-bromosuccinimide and fitting the data to the first-order reaction rate law. Recorded data were processed removing pretrigger time points and averaging replicates. The data were fit to a two-stage kinetic model (equations (4) and (5)) using the DynaFit software45 . Baseline anisotropy of the free fluorophore, substrate concentrations and dead time of the instrument were taken into account. The s.d. (normal distribution verified) and confidence intervals of fitted parameters were estimated with the Monte Carlo method46 (link) with standard settings (N = 1,000, 5% worst fits discarded). The derived parameters KD (dissociation constant) and kapp (apparent second-order rate constant) were calculated according to equations (6) and (7). P+Sk1k1PS* PS*k2PS KD=k1k1 kapp=k1k2k2+k1
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Publication 2021
Anisotropy Anisotropy, Fluorescence Biopharmaceuticals Bromosuccinimide Buffers Fluorescence Kinetics Proteins Seizures tryptophanamide
Bromide 11d was synthesized from (−)-nopol via reaction with NBS–PPh3, as described in [32 (link)].
Triphenylphosphine (2.0 equiv., 6.1 g, 23 mmol) was dissolved in dry DCM (23 mL) under argon. N-bromosuccinimide (NBS) (2.0 equiv., 4.2 g, 23 mmol) was added to this solution in small portions over 5 min in an ice-water bath. Subsequently, the resulting deep red mixture was stirred at room temperature for 30 min. Then, pyridine (1 mL) was added, and the color turned reddish-brown. (–)-Nopol (1.0 equiv., 2.0 mL, 12 mmol) was added to the mixture dropwise over 10 min. The reaction mixture was stirred overnight at room temperature. Later, the mixture was diluted with hexane (40 mL) and filtered through a silica gel plug. Then, the reaction flask was stirred with EtOAc–hexane (1:1, 40 mL) and filtered through the silica gel plug. Later, it was concentrated in vacuo and the crude residue was purified by chromatography on SiO2 (hexane) to obtain bromide 11d (2.3 g, 70% yield).
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Publication 2021
Argon Bath Bromides Bromosuccinimide Chromatography n-hexane nopol Pyridines Silica Gel triphenylphosphine

Most recents protocols related to «Bromosuccinimide»

Example 1

Reagents for peptide synthesis were purchased from Chem-Impex (Wood Dale, IL), NovaBiochem (La Jolla, CA), or Anaspec (San Jose, CA). Rink amide resin LS (100-200 mesh, 0.2 mmol/g) was purchased from Advanced ChemTech. Cell culture media, fetal bovine serum, penicillin-streptomycin, 0.25% trypsin-EDTA, and DPBS were purchased from Invitrogen (Carlsbad, CA). Methyl 3,5-dimethylbenzoiate, N-bromosuccinimide, diethyl phosphite, 2,2′-dipyridyl disulfide, and other organic reagents/solvents were purchased from Sigma-Aldrich (St. Louis, MO). Anti-GST-Tb and streptavidin-d2 were purchased from Cisbio (Bedford, MA). The NF-κB reporter (Luc)-HEK293 cell line and One-Step™ luciferase assay system were purchased from BPS Bioscience (San Diego, CA).

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Patent 2024
Anabolism Biological Assay Bromosuccinimide Cell Culture Techniques Cells Culture Media Disulfides Edetic Acid Fetal Bovine Serum HEK293 Cells Luciferases Penicillins Peptide Biosynthesis Phosphite RELA protein, human Rink amide resin Solvents Streptavidin Streptomycin Trypsin
In a 50 mL round-bottom
flask, compound 4 (0.15 g; 0.25 mmol) was dissolved in
30 mL of dichloromethane. N-Bromosuccinimide (0.2
g; 0.64 mmol) was dissolved in 10 mL of DCM and added to the reaction
mixture dropwise. After the addition, the reaction mixture was stirred
at room temperature for 3 h. The reaction mixture was extracted with
water (200 mL, three times) and the organic layer was dried over anhydrous
Na2SO4 and concentrated on a rotary evaporator
until the solvent was removed. Compound 5 was isolated
from column chromatography on silica gel (230–400 mesh) with
dichloromethane as the eluent (yield: 64%).
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Publication 2023
Bromosuccinimide Chromatography Gel Chromatography Methylene Chloride Silica Gel Silicon Dioxide Solvents
The
deuterated solvent (CDCl3)
used for NMR spectroscopy, silica gel 60 (230–400 mesh) for
column chromatography, trifluoroacetic acid, p-chloranil,
MB, DPBF, triethylamine, benzene, acetonitrile, sodium ascorbate,
copper sulfate pentahydrate, cresyl violet, and boron trifluoride
diethyl etherate were provided by Merck. The following chemicals were
obtained from Sigma-Aldrich: ethanol, methanol tetrahydrofuran, sodium
thiosulfate, dimethyl sulfoxide, 2,4-dimethylpyrrole, N,N-dimethylformamide, acetone, dichloromethane,
iodic acid, iodine, hexane, sodium sulfate, N-bromosuccinimide, and glacial acetic acid. n-Butylamine was purchased from Alfa Aesar. The following
chemicals were obtained from Acros Organics: piperidine and 4-hydroxybenzaldehyde.
Bromo-1,8-naphthalic anhydride was purchased from TCI. Zinc phthalocyanine
and 1-azido-1-deoxy-β-d-glucopyranoside tetraacetate
were purchased from ABCR. The rest of the chemicals used in the synthesis
were of reagent grade unless otherwise specified.
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Publication 2023
1,8-naphthalenedicarboxylic acid anhydride 4-hydroxybenzaldehyde Acetic Acid Acetone acetonitrile Benzene Boron Bromosuccinimide Chloranil Chromatography cresyl violet Dimethylformamide Ethanol Hexanes iodic acid Iodine Methanol Methylene Chloride oxytocin, 1-desamino-(O-Et-Tyr)(2)- piperidine Silica Gel Sodium Ascorbate sodium sulfate Solvents Spectroscopy, Nuclear Magnetic Resonance Sulfate, Copper Sulfoxide, Dimethyl tetrahydrofuran triethylamine Trifluoroacetic Acid Zinc
Azide-functionalized tetraphenylethene (TPE-N3) was synthesized in two steps with an 80% total yield. (1) Synthesis of 1-(4-methylphenyl)-1,2,2-triphenylethene. To a 250 mL two-necked round-bottom flask equipped with a stirring bar, 5.05 g (30 mmol) of diphenylmethane was added and dissolved in 100 mL of anhydrous THF. Then, the mixture was cooled down to 0 °C, and 15 mL (2.5 M in hexane, 37.5 mmol) of n-butyllithium was slowly added by a syringe. The mixture was stirred at 0 °C for 1 h. Next, 4.91 g (25 mmol) of 4-methylbenzophenone was added into the flask, and the mixture was warmed to room temperature and stirred overnight. The reaction mixture was then quenched with saturated NH4Cl solution and subsequently extracted with DCM (three times). Organic layers were collected and concentrated on a rotary evaporator under reduced pressure. The crude product with 0.20 g of p-toluenesulfonic acid was dissolved in 100 mL of toluene. The mixture was heated and refluxed for 4 h. After cooling to room temperature, the mixture was extracted with DCM (three times). The organic layers were collected and concentrated. The crude product was analyzed with LC–MS (purity > 95%) and was used in the next step without purification (4.08 g, 95% yield). HR-MS (MALDI-TOF): m/z 346.1701 [(M)+, calc. 346.1722]. (2) Synthesis of 1-[(4-bromomethyl)phenyl]-1,2,2-triphenylethene. In a 250 mL round-bottom flask, a mixture of 3.04 g (8.77 mmol) of 1, 1.80 g (9.77 mmol) of freshly recrystallized N-bromosuccinimide, and 0.025 g of benzoyl peroxide in 60 mL of CCl4 was refluxed for 12 h. After this time, the mixture was extracted with water and DMC (3×). The organic layers were combined and dried over magnesium sulfate, and the DCM was removed under reduced pressure. The crude product was purified by silica-gel chromatography using hexane as the eluent to yield 2 as a white solid (2.42 g, 65% yield).
Publication 2023
4-methylbenzophenone Acids Anabolism Azides Bromosuccinimide CCL4 protein, human Chromatography diphenylmethane Gel Chromatography n-butyllithium n-hexane Peroxide, Benzoyl Pressure Silica Gel Silicon Dioxide Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Sulfate, Magnesium Syringes Toluene
The compound was prepared using a reported protocol52 (link) with minor modifications. N,N-Bis(2-hydroxyethyl)aniline (500 mg, 2.8 mmol)
and N-bromosuccinimide (534 mg, 3.0 mmol) were dissolved
in dichloromethane (30 mL), and the mixture was stirred at room temperature
overnight. The solution was washed with a saturated aqueous solution
of sodium bicarbonate (3 × 20 mL) and dried over magnesium sulfate.
The solvent was removed under reduced pressure, and the crude product
purified by silica column chromatography with a linear gradient (0%/100%
to 100%/0% dichloromethane/hexane). The fractions containing the product
were combined, and the compound was dried under vacuum. Yield: 640
mg (2.5 mmol, 88%). 1H NMR (500 MHz, CD2Cl2): δ 7.27 (d, J = 9.1 Hz, 2H), 6.56
(d, J = 9.1 Hz, 2H), 3.77 (t, J =
4.9 Hz, 4H), 3.51 (t, J = 4.9 Hz, 4H). 13C{1H} NMR (125 MHz, CD2Cl2): δ
147.3, 132.1, 114.4, 108.5, 60.7, 55.6. HR-MS (m/z): [M + H]+ calcd for C10H15BrNO2, 260.0281; found, 260.0276.
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Publication 2023
1H NMR aniline Bicarbonate, Sodium Bromosuccinimide Carbon-13 Magnetic Resonance Spectroscopy Chromatography Methylene Chloride n-hexane Pressure Silicon Dioxide Solvents Sulfate, Magnesium Vacuum

Top products related to «Bromosuccinimide»

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N-bromosuccinimide is a chemical compound used as a laboratory reagent. It is a source of electrophilic bromine and is commonly utilized in organic synthesis reactions, such as bromination and substitution reactions.
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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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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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Dichloromethane is a clear, colorless, and volatile liquid commonly used as a laboratory solvent. It has a molecular formula of CH2Cl2 and a molar mass of 84.93 g/mol. Dichloromethane is known for its high solvent power and low boiling point, making it suitable for various laboratory applications where a versatile and efficient solvent is required.
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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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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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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.
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Chloroform is a colorless, volatile liquid with a characteristic sweet odor. It is a commonly used solvent in a variety of laboratory applications, including extraction, purification, and sample preparation processes. Chloroform has a high density and is immiscible with water, making it a useful solvent for a range of organic compounds.
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N-bromosuccinimide is a chemical reagent commonly used in organic synthesis. It is a source of electrophilic bromine and acts as a halogenating agent. N-bromosuccinimide is used in a variety of organic reactions, such as allylic bromination, benzylic bromination, and radical bromination.

More about "Bromosuccinimide"

Bromosuccinimide (BSN, NBS) is a versatile organic reagent used in a variety of chemical transformations, including halogenation, oxidation, and electrophilic substitution reactions.
It is a mild, selective, and efficient brominating agent that can be used to introduce bromine atoms into a wide range of organic compounds.
Bromosuccinimide is particularly useful in the synthesis of complex molecules, medicinal and pharmaceutical compounds, and natural products.
It is an essential tool in the chemist's toolkit, enabling the efficient and selective functionalization of organic substrates.
N-Bromosuccinimide (NBS) is a closely related compound that is often used interchangeably with Bromosuccinimide.
Both reagents share similar chemical properties and can be used in similar reactions.
Acetonitrile (ACN), Tetrahydrofuran (THF), N,N-Dimethylformamide (DMF), Dichloromethane (DCM), Methanol (MeOH), Triethylamine (TEA), Toluene, and Chloroform are common solvents and additives used in Bromosuccinimide-mediated reactions.
Researchers can optimize their Bromosuccinimide protocols using PubCompare.ai's AI-driven tools for literature search, protocol comparisons, and product identification.
This ensures reproducible and accurate results in their chemical transformations.
PubCompare.ai's cutting-edge AI tools enable researchers to locate protocols from literature, preprints, and patents, and use intelligent comparisons to identify the best protocols and products for their specific needs.