Benzyl ether

Manufactured by Merck Group

Sourced in United States, Germany, Spain, Belgium

Benzyl ether is a chemical compound used in laboratory settings. It is a colorless liquid with a characteristic odor. Benzyl ether serves as a solvent and intermediate in various organic synthesis reactions.

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Lab products found in correlation

Oleic acid, by Merck Group (41 mentions) Oleylamine, by Merck Group (31 mentions) 1 2 hexadecanediol, by Merck Group (21 mentions) Iron 3 acetylacetonate, by Merck Group (18 mentions) Iron acetylacetonate, by Merck Group (10 mentions) Chloroform, by Merck Group (9 mentions) Ethanol, by Merck Group (8 mentions) Hexane, by Merck Group (7 mentions) Toluene, by Merck Group (5 mentions) 1 octadecene, by Merck Group (5 mentions) Acetone, by Merck Group (5 mentions) Manganese acetylacetonate, by Merck Group (4 mentions) Tetrahydrofuran, by Merck Group (4 mentions) Acetonitrile, by Merck Group (4 mentions) Dimethyl sulfoxide (dmso), by Merck Group (4 mentions) N hydroxysuccinimide, by Merck Group (3 mentions) 1 2 tetradecanediol, by Merck Group (3 mentions) Hydrochloric acid (hcl), by Merck Group (3 mentions) Doxorubicin hydrochloride, by Merck Group (3 mentions) Lauric acid, by Merck Group (3 mentions)

66 protocols using benzyl ether

Nanoparticle Synthesis and Characterization

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1-Octadecene, MTT reagent, 4′-6-diamidino-2-phenylindole (DAPI, Thermo Fisher Scientific), acetone (≥99.9%) and acetonitrile (ACN; 99.8%), hexane (95%), iron pentacarbonyl (Fe(CO)₅), oleic acid (90%), PTX (Scinopharm), LST (Fluka), PBS (UniRegion Bio-tech), oleylamine (>70%), pluronic F-127 (Sigma-Aldrich Co., St Louis, MO, USA), sodium dodecyl sulfate gel, acrylamide/bis-acrylamide (40% solution, 29:1), N,N,N′,N′-tetramethylethylenediamine (~99%), trimethylamine N-oxide and ammonium persulfate (≥98%) were purchased from Sigma-Aldrich Co. Benzyl ether (99%), gelatin type A (from porcine skin), MMP-2 (≥98%), chloroform, N-hydroxysuccinimide (NHS) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) were purchased from Sigma-Aldrich Co. Formaldehyde was purchased from Riedel de Haen and Tri-ton X-100 from J.T. Baker. CdSe/ZnS core/shell QDs were obtained from Ocean Nanotech (Springdale, AR, USA). All chemicals and solvents were of analytical reagent grade.

Lai Y.H., Chiang C.S., Kao T.H, & Chen S.Y. (2018). Dual-drug nanomedicine with hydrophilic F127-modified magnetic nanocarriers assembled in amphiphilic gelatin for enhanced penetration and drug delivery in deep tumor tissue. International Journal of Nanomedicine, 13, 3011-3026.

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Synthesis of Fluorescent Nanoparticles

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Iron acetylacetonate (Fe(acac)₃ 99%), 1,2-tetradecanediol (technical grade, 90%), oleic acid (technical grade, 90%), oleylamine (technical grade, 70%), benzyl ether (98%), and 1,1′-dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate (DiI) were purchased from Sigma-Aldrich. 1,2-Distearoyl-snglycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (ammonium salt) (DSPE-PEG2000) were purchased from Avanti Polar Lipids. All chemicals were used as received.

Sifford J., Walsh K.J., Tong S., Bao G, & Agarwal G. (2019). Indirect magnetic force microscopy. Nanoscale Advances, 1(6), 2348-2355.

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Synthesis of Cobalt-Doped Superparamagnetic Iron Oxide Nanoparticles

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To enhance the magnetic properties of the SPION-loaded micelles, cobalt-doped superparamagnetic iron oxide nanoparticles (SPIONs) were synthesized, as previously described.^{58 (link)} The 10 nm cobalt-doped SPIONs could be readily synthesized in one step (i.e., vs. sequential seed growth) and efficiently loaded into the micelles. Briefly, 1 mmol cobalt chloride (Alfa Aesar), 2 mmol iron (III) acetylacetonate (Sigma), 2 mmol oleic acid (Chem-Impex International), 6 mmol oleylamine (Sigma), and 5 mmol 1, 2-hexadecanediol (Sigma) were reacted in 20 mL benzyl ether (Sigma) in a two-neck flask while stirred under nitrogen. The reaction was heated to 200°C for 30 minutes, followed by heating to reflux for 75 minutes. The product was cooled to room temperature and washed with 100% ethanol by centrifugation at 5,500 g × 15 minutes. The pellet was resuspended in toluene and large aggregates were removed by centrifugation at 3,000 g × 15 minutes.

Liu J.F., Lan Z., Ferrari C., Stein J.M., Higbee-Dempsey E., Yan L., Amirshaghaghi A., Cheng Z., Issadore D, & Tsourkas A. (2019). Use of Oppositely-Polarized External Magnets to Improve the Accumulation and Penetration of Magnetic Nanocarriers into Solid Tumors. ACS nano, 14(1), 142-152.

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Synthesis of Fluorescent Iron Oxide Nanoparticles

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Dextran T40 (Mw = 40 000 Da) and sodium periodate (NaIO₄, AR, 99.5%) were purchased from Aladdin CO. Ltd. (Shanghai, China). Sulfo-Cyanine 5 amine (sulfo-Cy5-NH₂) and Sulfo-Cyanine 5.5 amine (sulfo-Cy5.5-NH₂) were purchased from Xi’an Ruixi Biological Technology CO. Ltd (Xi’an, China). Iron (III) acetylacetonate (Fe(acac)₂, AR, 97%), 1,2-hexadecanediol (AR, 90%), benzyl ether (AR, 98%), potassium ferrocyanide (AR, 99%), oleic acid (AR, 70%) and oleylamine (OA, AR, 70%) were purchased from Sigma-Aldrich Corporation. All solvents and reagents were used as received. Dulbecco’s modified Eagle medium and fetal bovine serum were purchased from Invitrogen (California). The human liver cancer cell line HepG2 was obtained from the American Type Culture Collection.

Jiang L., Zheng R., Zeng N., Wu C, & Su H. (2022). In situ self-assembly of amphiphilic dextran micelles and superparamagnetic iron oxide nanoparticle-loading as magnetic resonance imaging contrast agents. Regenerative Biomaterials, 10, rbac096.

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Synthesis of Functionalized Nanoparticles

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Iron (III) acetylacetonate (99%), oleic acid (technical grade 90%), benzyl ether (98%), and BSA (98%) were purchased from Sigma-Aldrich (St. Louis, MO, USA) and used as received; 4-biphenylcarboxylic acid (99%, Acros Organics, Belgium, WI, USA), acetone (99.5%), hexanes (98.5%), sodium bicarbonate (99.7%), nitric acid (70%), and hydrogen peroxide (30%) were purchased from Fisher Scientific (Waltham, MA, USA). The BSA Cy5.5 conjugate (BSA Cy5.5, 10 mg·mL^‒1 in saline) was purchased from Protein Mods (Burlington, ON, Canada).

Cho M., Cervadoro A., Ramirez M.R., Stigliano C., Brazdeikis A., Colvin V.L., Civera P., Key J, & Decuzzi P. (2017). Assembly of Iron Oxide Nanocubes for Enhanced Cancer Hyperthermia and Magnetic Resonance Imaging. Nanomaterials, 7(4), 72.

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Synthesis of Magnetic Nanoparticles

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Iron (III) acetylacetonate (97%), 1,2-hexadecanediol (90%), benzyl ether (98%), oleic acid (OA, 70%) and oleylamine (OAm, 70%) were purchased from Sigma-Aldrich Corporation. Diethylenetriaminepentaacetic dianhydride (98%) was purchased from TCI Chemical Industry Development Corporation. NH₂-PEG-dopamine (Mw 1 k and 2 k) were purchased from Shanghai Ponsure Biotech, Inc. (Shanghai, China). Gadolinium (III) chloride (GdCl₃) and ethylenediaminetetraacetic acid disodium salt (EDTA2Na) were purchased from Aladdin Industrial Corporation. All other chemicals and solvents were of analytical grade and used without further purification.

Yang L., Fu S., Cai Z., Liu L., Xia C., Gong Q., Song B, & Ai H. (2021). Integration of PEG-conjugated gadolinium complex and superparamagnetic iron oxide nanoparticles as T1–T2 dual-mode magnetic resonance imaging probes. Regenerative Biomaterials, 8(6), rbab064.

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Synthesis of Multifunctional Magnetic Nanoparticles

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The chemicals used include
iron(III) chloride hexahydrate (FeCl₃·6H₂O) (≥98%, Aldrich), iron(III) acetylacetonate (Fe(acac)₃, 97%), manganese(II) acetylacetonate (Mn(acac)₂), sodium oleate (99%, TGI), oleic acid (90%, Aldrich), oleylamine
(70%, Sigma), 1,2-dodecanediol (90%, Sigma), Igepal CO-520 (Sigma),
tri-n-octylamine (95%, Fisher), benzyl ether (98%),
tetraethyl orthosilicate (TEOS) (≥99%, Sigma), 1H,1H,2H,2H-perfluorooctyltriethoxysilane
(PFOTES, 97%, Sigma), 1H,1H,2H,2H-perfluorodecyltriethoxysilane (PFDTES,
97%, Sigma), 1H,1H,2H,2H-perfluorodecyltrimethoxysilane (PFPE, 20% in
fluorinated hydrocarbon, MW = 4000–8000 g/mol, 22–46
repeat units, Gelest), silane PFPE_NH (MW = 989 g/mol, Surfactis
Technologies), ammonia solution (NH₄OH, 28–30%),
hexane (≥98.5%, Fisher), cyclohexane, and chloroform (99.9%,
EMD), HFE-7700, HFE-7200, HFE-7100, perfluorohexane (PFH, 3M), and
perfluorooctane (PFO, 3M).

Lin F.C., van de Wouw H.L., Campàs O., Sletten E.M, & Zink J.I. (2023). Synthesis of Fluorous Ferrofluids and Effects of the Nanoparticle Coatings on Field- and Temperature-Dependent Magnetizations. Chemistry of Materials, 35(19), 7957-7966.

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Synthesis of Monodisperse Nanoparticles

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In this study was used: iron (III) acetylacetonate (99%) from Sigma Aldrich (St. Louis, MO, USA), oleic acid (90%) from Panreac (Barcelona, Spain), benzyl ether (99%) from Sigma Aldrich (Madrid, Spain), 4-biphenylcarboxylic acid (99%) from Sigma Aldrich (Madrid, Spain), toluene (99.8%) from Panreac (Barcelona, Spain), hexane (99%) from Panreac (Barcelona, Spain), chloroform (99.9%) from Panreac (Barcelona, Spain), and nitrogen (99%) from Air Liquide (Paris, France). All solutions were made with distilled water.

Sánchez O.S., Castelo-Grande T., Augusto P.A., Compaña J.M, & Barbosa D. (2021). Cubic Nanoparticles for Magnetic Hyperthermia: Process Optimization and Potential Industrial Implementation. Nanomaterials, 11(7), 1652.

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Synthesis of Monodisperse Iron Oxide Nanoparticles

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All reactants used were commercially available: hexadecylamine (HDA) 98% purity, oleic acid (OA) 99% purity, iron pentacarbonyl, di benzyl ether 98% purity, ethyl acetate (99.5% purity), tetramethylammonium hydroxide (TMAH) solution in water (25% wt), and benzyl ether (98% purity) were purchased from Sigma-Aldrich Saint Louis, MO, USA and were used as received. Absolute ethanol and n-hexane 99% reagent grade were supplied by Scharlau, Cham Germany.

Reyes-Ortega F., Delgado Á.V, & Iglesias G.R. (2021). Modulation of the Magnetic Hyperthermia Response Using Different Superparamagnetic Iron Oxide Nanoparticle Morphologies. Nanomaterials, 11(3), 627.

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Nanoparticle-Encapsulated Tetrandrine Delivery

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Iron(iii) acetylacetonate, chloroform, oleic acid and oleylamine were purchased from Strem Chemicals, Inc. Postfach, Kehl, Germany. 1,2-Hexadecanediol and benzyl ether were obtained from Sigma-Aldrich, St. Louis, MO, USA. PLGA (Resomer RG 503, MW: 24 000–38 000 Da) was purchased from Evonik Industries, Germany. Tetrandrine (Tet, >98%) was obtained from Wuhan Dinghui Chemical Co., Ltd, China. Polyvinyl alcohol (PVA, Mowiol 4-88) was obtained from Kuraray Specialties Europe GmbH, Frankfurt, Germany. The PromoKine Annexin V-FITC Detection Kit was purchased from PromoCell GmbH, Heidelberg, Germany. BCA protein assay kits were purchased from BioRad, Hercules, USA. The antibodies for Cathepsin B, Bcl-2, Smac/Diablo, XIAP, Cytochrome C, Caspase 3, β-actin and GAPDH were obtained from Cell Signaling Technology, Danvers, MA, USA.

Wu T., Zhang Q., Hu H., Yang F., Li K., Zhang Y, & Shi C. (2020). Enhancing cellular morphological changes and ablation of cancer cells via the interaction of drug co-loaded magnetic nanosystems in weak rotating magnetic fields. RSC Advances, 10(25), 14471-14481.

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