Benzoin, sodium borohydride (NaBH4, ≥98.0%), 4-nitrobenzoyl chloride (4-NBC, 98%), methanol (MeOH, ≥99.8%), tetrahydrofuran (THF, ≥99.9%), N,N’-dimethylacetamide (DMAc, ≥99.8%), pyromellitic dianhydride (PMDA), and 4,4′-oxydianiline (ODA) were purchased from Sigma-Aldrich Korea (Seoul, Korea). Solvents such as N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), N-methyl pyrrolidone (NMP), chloroform (CHCl3), and ethanol were purchased from Junsei Chemical Co (Tokyo, Japan). As for 4,4-Diphthalic anhydride (6-FDA, ≥98.0%) and 10% palladium on carbon (Pd/C), they were purchased from Tokyo Chemical Industry Co. (TCI) (Tokyo, Japan). n-Hexane, ethyl acetate, and dichloromethane were purchased from Samchun Pure Chemicals (Pyeongtaek, Korea). Celite 545, which is a kind of diatomite whose main component is silica and is used to separate a catalyst from the reaction mixture, and γ-butyrolactone were purchased from Daejung (Siheung, Korea). The deionized water used in the experiments was purified by a Direct-Q®3 water purification system (EMD Millipore) (Busan, Korea). All purchased chemical reagents were used without further purification.
Benzoin
Manufactured by Merck Group
Sourced in United States
Benzoin is a laboratory equipment used for the preparation and purification of organic compounds. It is a type of heating device that uses an open flame or electric heating element to gently heat and evaporate solvents, facilitating the crystallization of desired substances.
Automatically generated - may contain errors
Lab products found in correlation
Methanol, by Merck Group (2 mentions)
Direct q3 water purification system, by Merck Group (1 mentions)
Tetrahydrofuran, by Merck Group (1 mentions)
Sodium borohydride, by Merck Group (1 mentions)
N n dimethylacetamide, by Merck Group (1 mentions)
4 nitrobenzoyl chloride, by Merck Group (1 mentions)
4 4 oxydianiline, by Merck Group (1 mentions)
N n dimethylformamide (dmf), by Junsei (1 mentions)
Ethyl acetate, by Samchun (1 mentions)
Ethanol, by Junsei (1 mentions)
Dichloromethane, by Samchun (1 mentions)
N hexane, by Samchun (1 mentions)
Salicylic acid, by Merck Group (1 mentions)
Vanillin, by Merck Group (1 mentions)
Thymol, by Merck Group (1 mentions)
4 hydroxybenzaldehyde, by Merck Group (1 mentions)
4 aminophenol, by Merck Group (1 mentions)
Dpph 2 2 diphenyl 1 picrylhydrazyl, by Merck Group (1 mentions)
Picric acid, by Merck Group (1 mentions)
Tyrosin, by Merck Group (1 mentions)
7 protocols using benzoin
1
Organic Synthesis of Aromatic Diamine Precursors
2
Synthesis and Characterization of Novel Organic Compounds
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All the chemicals and reactants used in this study were of analytical grade. Methanol, Benzoin, vanillin, picric acid, 4-amino phenol, dichlorophenol, 4-hydroxy benzaldehyde, tyrosin, thymol, alpha-naphthol, and beta-naphthol were purchased from Sigma Chemicals (St. Louis, MO, USA). DPPH (2, 2-diphenyl-1-picrylhydrazyl) and salicylic acid were purchased from Merck (Darmstadt, Germany). 2-(N-((2′-(2H-tetrazole-5-yl)-[1,1′-biphenyl]-4yl)-methyl)-pentanamido)-3-methyl butanoic acid (96%, USP grade) was obtained from Highnoon laboratories Pvt. Ltd., Lahore, Pakistan. Using the Gallen Kamp melting point apparatus, melting points were recorded. 1H and 13C nuclear magnetic resonance analysis was performed. The cary630 FTIR spectrophotometer was used to generate a Fourier transform infrared (FTIR) spectrum using the KBr pellet press technique. The glassware was dried in a UN55 (Memmert) oven at 200 °C. In 1.0 mM of each reactant, the % yields of derivatives are provided.
3
Synthesis of Benzoin-Biphenylsulfonyl Derivative
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Example 27
Benzoin (Sigma-Aldrich) (7.64 g, 0.036 mole) and 4,4′-biphenylsulfonyl chloride (TCI) (7.02 g, 0.02 mole) were suspended in methyl ethyl ketone (30 mL) and the contents were cooled in an ice/water bath. Sodium hydroxide (1.8 g, 0.045 mole) in water (4.2 g) was added drop wise. After the addition, the mixture was stirred in the ice bath for 3 hours and was then warmed to room temperature and stirred for 17 hours. The mixture was filtered through a filter paper and the filterate was placed in the refrigerator. The precipitated solid was filtered and washed with 3×100 mL DI water followed by 50 mL cold methyl ethyl ketone. The solid was suction dried overnight to give 1.66 grams of the crude product. This solid was then recrystallized from ethyl acetate. 1H NMR (400 MHz, Chloroform-d), delta (ppm): 8.00-7.92 (d, 4H), 7.92-7.85 (d, 4H), 7.65-7.58 (d, 4H), 7.58-7.52 (t, 2H), 7.45-7.35 (m, 8H), 7.35-7.30 (m, 6H), 6.82 (s, 2H).
4
Synthesis and Characterization of Thiosemicarbazone
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Thiosemicarbazides readily condense with carbonyl compounds to form thiosemicarbazones in an alcohol medium. Benzoin (2.1 g, 0.01 mol) (Sigma Aldrich) and MPTSC (1.8 g, 0.01 mol) in 50 cm3 ethanol were refluxed well for 2 h in the presence of 2 cm3 of p-toluene sulfonic acid as a catalyst on a water bath. The mixture was concentrated to reduce the volume to half and kept for half an hour. The yellow precipitate formed was filtered and washed with cold ethanol (m.p. 116 °C).
The follow-up of the reaction rates was performed by thin-layer chromatography (TLC) on glass sheets precoated with silica gel, and the spots were visualized by exposure to iodine vapors. The percentages of carbon, hydrogen, and nitrogen in the compound were determined using a Hitachi CHN rapid analyzer and that of sulfur by Kjeldahl’s method. The IR spectra of the compound using KBr disks were recorded on a Shimadzu FTIR-8101A spectrophotometer with a scanning range of 400–4000 cm−1. 1H NMR spectrum of the compound was recorded in DMSO-d6 by using 300 MHz Bruker Advanced DPX spectrometer. The data were recorded as chemical shifts expressed in δ (ppm) relative to tetramethylsilane (TMS) as the internal standard. 13C NMR spectrum of the compound was recorded in DMSO using a Bruker NMR spectrometer.
The follow-up of the reaction rates was performed by thin-layer chromatography (TLC) on glass sheets precoated with silica gel, and the spots were visualized by exposure to iodine vapors. The percentages of carbon, hydrogen, and nitrogen in the compound were determined using a Hitachi CHN rapid analyzer and that of sulfur by Kjeldahl’s method. The IR spectra of the compound using KBr disks were recorded on a Shimadzu FTIR-8101A spectrophotometer with a scanning range of 400–4000 cm−1. 1H NMR spectrum of the compound was recorded in DMSO-d6 by using 300 MHz Bruker Advanced DPX spectrometer. The data were recorded as chemical shifts expressed in δ (ppm) relative to tetramethylsilane (TMS) as the internal standard. 13C NMR spectrum of the compound was recorded in DMSO using a Bruker NMR spectrometer.
5
Polyester Resin Crosslinking Synthesis
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The 3-amino-1,2-propanediol (Aldrich, ≥99%), furan (Merck, Darmstadt, Germany stabilized, ≥99%) Maleic anhydride (Merck, Darmstadt, Germany) were used as received. Furfuryl alcohol (Merck, Darmstadt, Germany, ≥98%) was dried with Na2SO4 and distilled under reduced pressure before use. Ethyl acetate, toluene (Acros organics, Thermo Fisher Scientific, Geel, Belgium, ≥99.8%), ethanol absolute (VWR International, Darmstadt, Germany), petroleum ether (Honeywell, Charlotte, NC, USA), and tetrahydrofuran (Acros, organics, Thermo Fisher Scientific, Geel, Belgium, ≥99.6%) were all analytical grade and used as delivered. The hydroxyl functional polyester resin (Crylcoat 2839-0, Allnex, Frankfurt, Germany) and Vestagon BF1320 uretdione cross-linker (Evonik, Essen, Germany) was used without any further modification. The OH group value of polyester resin and the NCO (lat.) content of the cross-linker was measured to be 50 mg KOH/g and 14.17%, respectively. All the samples were prepared in a way that the NCO: OH ratio was 1:1. Resiflow 88 (Worlée, Hamburg, Germany) and benzoin (Sigma-Aldrich, St. Louis, MO, USA) were used as a flow agent and degassing agent, respectively.
6
Functionalization of Mono-(6-amino-6-deoxy)-β-Cyclodextrin
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Mono-(6-amino-6-deoxy)-β-cyclodextrin (NH2-β-CD, purity ≥98%) was purchased from Shandong Binzhou Zhiyuan Biotechnology Co (Binzhou, China). 4,4′-Thiobisbenzenethiol (purity ≥98%), 2,2′-azobis(2-methylpropionitrile) (AIBN, purity ≥98%), 3-isocyanatopropyltriethoxysilane (purity ≥98%), formic acid (FA), acetic acid (HOAc), and triethylamine (TEA) were purchased from Shanghai Aladdin Bio-Chem Technology Co (Shanghai, China). Allyl isocyanate (purity ≥98%) was obtained from Alfa Aesar (Tewksbury, MA, USA). Pyridine and acetone were provided by Sinopharm Chemical Reagent Co (Shanghai, China). Methanol (MeOH) and acetonitrile (ACN) (HPLC grade) purchased from Tedia (Shanghai, China). Sephadex C-25 was provided by Rui Da Heng Hui Science Technology Development Co (Beijing, China). Triazole racemic standards (purity ≥98%) were purchased from Shanghai Pesticide Research Institution (Shanghai, China). Flavanones, benzoin, praziquantel, 1,1-bi-2-naphthol, Tröger's base, and bicalutamide racemic standards were obtained from Sigma-Aldrich (St. Louis, MO, USA). Spherical silica gel (5 μm, 25 nm) was provided by Lanzhou Institute of chemical physics (Lanzhou, China). Pyridine was treated with calcium hydride and distilled before use. The water was of ultrapure grade.
7
Synthesis of Polymeric Materials with Varying AA Content
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Two different polymeric materials were synthesized with different proportions of EA(Sigma-Aldrich), EMA (Sigma-Aldrich) and AA (Scharlau). The first material, p(EA-EMA-0%AA), was composed of 50% EA, 50% EMA and 0% AA; and the second, p(EA-EMA-5%AA), of 47.5% EA, 47.5% EMA and 5% AA. The polymerization was a free radical reaction, achieved by mixing all the monomers in the desired proportion and using acetone 30 wt% (Scharlau) as solvent and benzoin 0.5 wt% (Sigma-Aldrich) as initiator. The resulting solution was polymerized for 24 hours in an ultraviolet oven. The polymeric blocks thus obtained underwent a thermal post-polymerization process for 24 hours at 90ºC in another oven (Memmert GmbH + Co.KG, Germany) to ensure total monomer conversion. After polymerization the remaining low molecular weight substances were extracted by repeated dissolution and precipitation, for which the copolymers were diluted in acetone, re-precipitated with deionized water and then dried for 3 days at 60ºC in oven, repeating the process three times.
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