Phenylboronic acid

Manufactured by Thermo Fisher Scientific

Sourced in United States

Phenylboronic acid is a chemical compound with the formula C6H7BO2. It is a crystalline solid that is used as a building block in organic synthesis and as a reagent in various chemical reactions.

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11 protocols using phenylboronic acid

Polymer-Mediated Synthesis of Substituted Aromatics

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Poly(methyl
vinyl ether-alt-maleic anhydride) (PMVEMA) (average M_w ∼ 216 kDa, average M_n ∼
80 kDa), polyethyleneimine (PEI)–branched (average M_w ∼ 800 Da, average M_n ∼ 600 Da), 4-iodotoluene (99%), 4-iodoanisole
(99%), 4-bromoanisole (99%), and bromobenzene (99%) were used as received
from Sigma-Aldrich. Ethanol (200 proof, 100%, bioreagent grade), potassium
carbonate (99%), sodium borohydride (98%; granules ca. 3 mm), potassium
tetrachloropalladate(II) (99.99% metals basis), 4-bromotoluene (99%),
phenyl boronic acid (98%+), dimethyl sulfoxide (DMSO) (99.7%+), 4-bromophenol
(98 + %), 4-bromobenzotrifluoride (98%+), 4-bromobenzonitrile (97%+),
4-methylbenzeneboronic acid (98%), 4-(trifluoromethoxy)phenylboronic
acid (98%), 4-nitrophenol (99%), 4-chloronitrobenzene (98%+), 2,6-dimethylnitrobenzene
(99%+), 4-nitrobenzonitrile (97%), 4-(2-fluoro-4-nitrophenyl)morpholine
(98%), 3-fluoro-4-morpholinoaniline (98%+), 2,6-dimethylaniline (99%),
4-aminobenzonitrile (98%+), 4-aminophenol (98%), 4-chloroaniline (98%),
4-methylbiphenyl (98%+), 4-methoxybiphenyl (98%+), 4-phenylphenol
(97%), 4-cyanobiphenyl (95%), 4,4′-dimethylbiphenyl (99%),
4,4′-biphenol (97%), and biphenyl-4,4′-dicarbonitrile
(98%) were used as received from Fisher Scientific. Water (18.2 MΩ)
was filtered, purified, and deionized using a PURELAB Flex 3.

Davis B.A., Genzer J., Efimenko K, & Abolhasani M. (2023). Continuous Ligand-Free Catalysis Using a Hybrid Polymer Network Support. JACS Au, 3(8), 2226-2236.

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Synthesis of Gold Nanoparticles

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Gold salt (HAuCl₄·3H₂O), trisodium citrate dihydrate, N,N’-methylene-bis-acrylamide (BIS), ammonium persulfate (APS), potassium carbonate (K₂CO₃), phenylboronic acid, cetyltrimethylammonium bromide solution (CTAB), L-ascorbic acid (ASA), and ethanol (EtOH) were purchased from Fisher Scientific. N-isopropylacrylamide (NIPAM) was purchased from Sigma-Aldrich and recrystallized in hexanes prior to use. Water used in all reactions was obtained from a Nanopure water system equipped with a 0.2 µm membrane filter (Barnstead/Thermolyne). All glassware was cleaned with a strong acid (3:1 ratio of HCl:HNO₃) and a base (KOH in isopropanol).

Hou J., Lartey J.A., Lee C.Y, & Kim J.H. (2024). Light-enhanced catalytic activity of stable and large gold nanoparticles in homocoupling reactions. Scientific Reports, 14, 1352.

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Synthesis of Gold Nanoparticles

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Ammonium persulfate (APS, >98%), potassium persulfate (KPS, >99%), N,N’-methylenebis-acrylamide (BIS, 99%), nitric acid, hydrochloric acid (HCl), trisodium citrate dehydrate (99%), potassium carbonate (K₂CO₃, >99%), potassium hydroxide (KOH, 99.98%), phenylboronic acid (>98%), biphenyl (99%), absolute ethanol (EtOH), and hydrogen tetrachloroaurate trihydrate (HAuCl₄∙3H₂O, 99.995%) were obtained from Fisher Scientific. N-isopropylacrylamide (NIPAM, 99%, Aldrich) was recrystallized in hexanes and dried under vacuum prior to use. All glassware was cleaned with a strong acid solution and a base bath. The water used in all reactions was obtained from a Nanopure water system (Barnstead/Thermolyne).

Hou J., Li B., Jang W., Yun J., Eyimegwu F.M, & Kim J.H. (2023). Integration of Gold Nanoparticles into Crosslinker-Free Polymer Particles and Their Colloidal Catalytic Property. Nanomaterials, 13(3), 416.

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Fluorescent Lipid Nanoparticle Formulation

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PFP (99%, Exfluor Research Corporation, Round Rock, TX, USA) was used as the US contrast agent. Monostearoyl-2-hydroxy-sn-glycero-3-phosphocholine (MSPC), 1,2-dipalmitoylsn-glycero-3-phosphocholine (DPPC), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy (PolyEthylene glycol)2000] (DSPE-mPEG2000 ) were obtained from Corden Pharma Corporation (Boulder, CO, USA). 1,2-Dihexadecanoyl-sn-Glycero-3-Phosphoethanolamine, Triethylammonium Salt (Lissamine^™ Rhodamine B) was obtained from Thermo Fisher Scientific Inc., and PKH67 Green Fluorescent Cell Linker was obtained from Sigma Aldrich (Milwaukee WI, USA). Dox was obtained from LC Laboratory (Woburn, MA, USA). Acetonitrile (high performance liquid chromatography (HPLC) grade) was obtained from Pharmco-AAPER (Brookfield, CT, USA). Ethylene glycol (99%, spectrophotometric grade), phenylboronic acid (98%), and 2,2-dimethoxypropane (98%) were purchased from Alpha Aesar (Ward Hill, MA, USA). The PD-10 column was obtained from GE Healthcare Life Sciences, (Buckinghamshire, United Kingdom, UK). C26 cells were kindly provided by the National Cancer Institute.

VanOsdol J., Ektate K., Ramasami S., Maples D., Collins W., Malayer J, & Ranjan A. (2016). Sequential HIFU heating and nanobubble encapsulation provide efficient drug penetration from stealth and temperature sensitive liposomes in colon cancer. Journal of controlled release : official journal of the Controlled Release Society, 247, 55-63.

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Development of Perfluoropentane Contrast Agent

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Perfluoropentane (99%, Exfluor Research Corporation, Texas, USA) was used as the US contrast agent. Monostearoyl-2-hydroxy-sn-glycero-3-phosphocholine (MSPC), 1,2-dipalmitoylsn-glycero-3-phosphocholine (DPPC), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy (PolyEthylene glycol)2000] (DSPEPEG2000) were obtained from Corden Pharma Corporation (Colorado, USA). Dox was obtained from LC laboratory (MA, USA). Agarose and psyllim fiber were purchased from BDH (Pennsylvania, USA) and Konsyl Pharmaceuticals, (Maryland, USA), respectively. Graphite was purchased from Alpha Aesar, Ward Hill, MA. Acetonitrile (HPLC grade) was obtained from Pharmco-AAPER (Connecticut, USA). Ethylene glycol (99%, spectrophotometric grade), phenylboronic acid (98%), and 2,2-dimethoxypropane (98%) were purchased from Alpha Aesar (Massachusetts, USA). C26 cells were kindly provided by the National Cancer Institute. PC3 prostate and A549 lung cancer cells were kindly provided by Dr. Elankumaran Subbiah (Virginia Tech), and Dr. Lin Lin (Oklahoma State University).

Maples D., Mclean K., Sahoo K., Newhardt R., Venkatesan P., Wood B, & Ranjan A. (2015). Synthesis and characterization of ultrasound imageable heat-sensitive liposomes for HIFU therapy. International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group, 31(6), 674-685.

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Deuterated Compound Synthesis and NMR Analysis

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d-(+)-Xylose (>99%), D₂O (99.9% atom D), toluene-d₈ (99% atom D), 3-(trimethylsilyl)propionic-2,2,3,3-d₄ acid sodium salt (TMSP, 98% atom D), 1-methylnaphthalene (98%), sodium sulfate (99%), sulfolane (99%) were purchased from Sigma-Aldrich, while phenylboronic acid (PBA, 99%), dioxane (99%) and tetramethylsilane (TMS) were obtained from Alfa Aesar.

Ricciardi L., Verboom W., Lange J.P, & Huskens J. (2022). Kinetic model for the dehydration of xylose to furfural from a boronate diester precursor. RSC Advances, 12(49), 31818-31829.

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Formulation and Characterization of Doxorubicin-Loaded Nanoparticles

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PFP (99%, Exfluor Research Corporation, TX, USA) was used as the US contrast agent. Monostearoyl-2-hydroxy-sn-glycero-3-phosphocholine (MSPC), 1,2-dipalmitoylsn-glycero-3-phosphocholine (DPPC), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy (polyEthylene glycol)2000] (DSPE-mPEG2000) were obtained from Corden Pharma Corporation (CO, USA). Dox was obtained from LC laboratory (MA, USA). Agarose and psyllim fiber were purchased from BDH (PA, USA) and Konsyl Pharmaceuticals, (MD, USA), respectively. Graphite was purchased from Alpha Aesar (Ward Hill, MA, USA). Acetonitrile (HPLC grade) was obtained from Pharmco-AAPER (CT, USA). Ethylene glycol (99%, spectrophotometric grade), phenylboronic acid (98%), and 2,2-dimethoxypropane (98%) were purchased from Alpha Aesar. The PD-10 column was obtained from GE Healthcare Life Sciences (Buckinghamshire, UK). C26 cells were kindly provided by the National Cancer Institute.

Ektate K., Kapoor A., Maples D., Tuysuzoglu A., VanOsdol J., Ramasami S, & Ranjan A. (2016). Motion Compensated Ultrasound Imaging Allows Thermometry and Image Guided Drug Delivery Monitoring from Echogenic Liposomes. Theranostics, 6(11), 1963-1974.

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Palladium-Catalyzed Suzuki-Miyaura Coupling

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Palladium-(II) chloride (PdCl₂, 99.99%), phenylboronic acid (C₆H₇BO₂, >98%), and 4-iodotoluene (C₇H₇I, 98%) were purchased from Alfa Aesar. Polyvinylpyrrolidone (PVP, M_W = 40 000), 4-nitrophenol (O₂NC₆H₄OH, ≥99%), substituted nitroarenes, and sodium borohydride (NaBH₄, >99%) were purchased from Sigma Aldrich. Ethanol (ACS grade), ethylene glycol (ACS grade), and isopropanol (ACS grade) were purchased from Merck. Ethyl acetate (LR) and hexane (LR) were purchased from Rankem. Anhydrous potassium carbonate (K₂CO₃, 99%) was purchased from Loba Chemie. Hydrochloric acid (HCl, 35% AR) was purchased from Himedia. Ultrapure water with a resistivity of 18.2 MΩ cm⁻¹ was used for all experiments. All chemicals were used without further purification.

Sahoo L., Dhindsa P.K., P N.C, & Gautam U.K. (2021). ‘Pre-optimization’ of the solvent of nanoparticle synthesis for superior catalytic efficiency: a case study with Pd nanocrystals. Nanoscale Advances, 3(8), 2366-2376.

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Synthesis of Phosphonium Salts

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All procedures associated with the preparation of the starting reagents, synthesis, and isolation of products were carried out under inert atmosphere using the standard Schlenk technique. Tri-tert-butylphosphine (Dal-Chem, Nizhny Novgorod, Russia), ethyl iodide and n-alkyl bromide (Sigma-Aldrich, St. Louis, MO, USA), phenylboronic acid (Alfa Aesar, Heysham, Lancashire, UK), 1,3,5-tribromobenzene (Alfa Aesar), Pd(OAc)₂ (Alfa Aesar), KOH (Himreaktiv, Nizhny Novgorod, Russia), NaBF₄ (Himreaktiv, Nizhny Novgorod, Russia) analytical grade, without additional purification were used in the work. Detailed synthesis and characterization of the phosphonium salts described in Supplementary Materials.

Arkhipova D.M., Ermolaev V.V., Miluykov V.A., Gubaidullin A.T., Islamov D.R., Kataeva O.N, & Ananikov V.P. (2020). Sterically Hindered Phosphonium Salts: Structure, Properties and Palladium Nanoparticle Stabilization. Nanomaterials, 10(12), 2457.

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Suzuki-Miyaura Coupling of Aryl Halides

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A test tube with a magnetic stirring bar was loaded with 1-bromo-4-nitrobenzene 1 (202 mg, 1.0 mmol, Sigma-Aldrich, 99%), phenylboronic acid 2 (146 mg, 1.2 mmol, Acros Organics, 99%), potassium carbonate (166 mg, 1.2 mmol, Acros Organics, >99%), 0.1 mol% Pd/C (10.6 mg, 1 μmol, Acros Organics), 1.6 mL of ethanol (Ferain, 95%) and 0.4 mL of H₂O. The reaction mixture was stirred for 5 hours at 70°C and was analyzed by ¹H NMR (Fig 7). The diameter of Pd nanoparticles at the commercial catalyst was 2.8 ± 0.7 nm, and the surface area of the catalyst was 1157 m²/g [49 ]. Commercially available reagents were used in the reaction.

Gordeev E.G., Galushko A.S, & Ananikov V.P. (2018). Improvement of quality of 3D printed objects by elimination of microscopic structural defects in fused deposition modeling. PLoS ONE, 13(6), e0198370.

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