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8 protocols using n butylamine

1

In-Situ Silica-Reinforced SSBR Composites

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Solution styrene butadiene rubber (SSBR) BUNA 2525-2 VSL HM containing 25% vinyl content and 25% styrene content was supplied by Lanxess, Cologne, Germany. Tetrahydrofuran (THF), N-butyl amine, sulfur, zinc oxide, and stearic acid were acquired from Acros Organics, Germany. The vulcanizing accelerators N-cyclohexyl 2-benzothioazolesulfonamide (CBS-Vulkacit CZ) and diphenyl guanidine (DPG) were delivered by Lanxess, Germany. The precursor for the in-situ silica generation tetraethoxyorthosilicate (TEOS) was obtained from Sigma Aldrich (Munich, Germany) with a purity of 90%. The precipitated silica (Ultrasil VN-3) exhibiting a BET surface of 175 m2/g and a purity of 99% and the silane coupling agent bis[3-(triethoxysilyl)propyl]tetrasulfide (TESPT) were kindly provided by Evonik Industries, Essen, Germany.
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2

Synthesis and Characterization of Ionic Liquids

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Zinc nitrate hexahydrate (98%), 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (≥98% HPLC) and deuterated NMR solvents: DMSO-d 6 (99.9 atom% D) with 0.03% (v/v) TMS and 35 wt% DCl in D 2 O (≥99 atom% D) were all purchased from Sigma Aldrich. 2-Methylimidazole (99%), n-butylamine (99+%) and sodium bis(trifluoromethanesulfonyl)imide (98%) were purchased from Acros Organics. The solvents methanol (certified AR for analysis) and chloroform (for HPLC, stabilised with Amylene) were purchased from Fisher
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3

Synthesis of Vanillin-Based Macromolecules

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Commercial grade ethyl acetate (≥98%), hexanes (≥98%), dichloromethane (≥99%) and ethanol (≥96%) were obtained from RCI Labscan (Bangkok, Thailand) and used as received from commercial suppliers without further purification. Boron oxide (≥98%), acetyl acetone (≥99%), vanillin (99%), tributyl borate (≥99%), 4-(N,N-dimethylamino)pyridine (DMAP) and succinic acid monoethyl ester chloride (95%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). n-Butylamine (99.5%) was procured from ACROS Organics (Geel, Belgium ). n-Octanol was obtained from Merck (Darmstadt, Germany). Water was produced in-house using a Milli-Q water purification system (Millipore S.A.S, Molsheim, France)
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4

Organic Synthesis Reagent Characterization

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Vanillin (99%, Acros Organics), 2,4-pentanedione (99.5%, Acros Organics), Boron oxide (99%, Acros Organics) and n-butylamine (99.5%, Acros Organics) were used as received. N,N-dimethylacetamide (DMAC, 99.5%, Fisher), chloroform (CT, 99.8%, Fisher), isopropanol (iPr, 99.5%, Acros Organics), nhexane (HEX, 99.8%, Fisher) and n-butyl acetate (BuAc, 99.8%, Fisher) used as solvents and stored in 2.5 L glass bottles stored under nitrogen atmosphere.
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5

Synthesis and Characterization of mPEG-Peptide Conjugates

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Triphosgene, n-butyl amine, diethylenetriamine, and β-benzyl L-aspartate (BLA) were purchased from Alfa Aesar (Tewksbury, MA, USA). Enhanced green fluorescent protein (EGFP) mRNA and firefly luciferase (Fluc) mRNA were purchased from TriLink BioTechnologies (San Diego, CA, USA). mPEG-succinimidyl carboxymethyl ester (mPEG(2k)-SCM) was obtained from Biopharma PEG Scientific Inc (Watertown, MA, USA). Calcein AM fluorescent dye was purchased from BD Biosciences (San Jose, CA, USA). NucBlue Live ReadyProbes Reagent, D-luciferin sodium salt monohydrate, Quant-it RiboGreen RNA Assay Kit, and HEPES buffer solution were purchased from Thermo Fisher Scientific (Waltham, MA, USA). BDP TR NHS ester and Cyanine7.5 NHS ester were obtained from Lumiprobe (Hunt Valley, MD, USA). All other reagents were of analytical grade and were obtained from Sigma-Aldrich Inc (Milwaukee, WI, USA) or Fisher Scientific Inc. (Hampton, NH, USA).
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6

Heterogeneous Catalytic Synthesis Protocol

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As received, ethyl acetoacetate, n-butylamine, resorcinol, acetonitrile, pyridine, cesium nitrate (CsNO3), ammonium hydroxide (NH4OH), zirconium oxynitrate (ZrO(NO3)2), 12-tungstophosphoric acid (H3PW12O40:PW), methylene blue (MB), and sulfuric acid (H2SO4) were obtained from Alfa Aeser. Both cetyltrimethylammonium bromide (N-cetyl-N,N,N-trimethyl ammonium bromide, CTAB) and tetraethyl orthosilicate (TEOS) were analytical-grade reagents.
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7

Fluorinated Amino Acid Synthesis

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4‐Benzyl‐L‐aspartate, 4‐nitrophenyl chloroformate, dithiothreitol, trifluoromethanesulfonic acid, and trifluoroacetic acid were obtained from TCI (Eschborn, Germany). L‐phenylalanine was purchased from Carl Roth (Karlsruhe, Germany). S‐carbobenzoxy‐L‐cysteine was obtained from BLD Pharmatech GmbH. Anhydrous dimethylacetamide (DMAc) was obtained from Acros (Geel, Belgium). S‐Benzyl‐L‐cysteine, hydrogen peroxide, and n‐butylamine were purchased from Alfa Aesar (Kandel, Germany). PFD was obtained from Fluorochem Chemicals (Derbyshire, UK). Methanol, ethyl acetate and diethyl ether were purchased from Fisher Scientific (Schwerte, Germany). Finally, n‐hexane and dichloromethane were obtained from VWR International (Darmstadt, Germany) and acetonitrile was purchased from Carl Roth (Karlsruhe, Germany).
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8

Synthesis of Fluorescent Probes

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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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