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Anhydrous dioxane

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Anhydrous dioxane is a colorless, volatile organic compound used as a laboratory solvent. It is a cyclic ether with the chemical formula C4H8O2. Anhydrous dioxane is primarily used in chemical synthesis and analysis, where it serves as a versatile solvent due to its ability to dissolve a wide range of organic compounds.

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Lab products found in correlation

Lc tof mass spectrometer, by Waters Corporation (2 mentions) 500 mhz fourier transform nmr spectrometer, by Bruker (2 mentions) Toluene, by Merck Group (1 mentions) 2 methf, by Merck Group (1 mentions) Silica gel, by Silicycle (1 mentions) Tetrahydrofuran thf, by Chem-Supply (1 mentions) Cdcl3, by Merck Group (1 mentions) Tin 2 2 ethylhexanoate, by Merck Group (1 mentions) Methanol, by Chem-Supply (1 mentions) Dichloromethane dcm, by Chem-Supply (1 mentions) Formaldehyde, by Thermo Fisher Scientific (1 mentions) Nupage 4 12 bis tris gel, by Thermo Fisher Scientific (1 mentions) Mes buffer, by Thermo Fisher Scientific (1 mentions) Lds buffer, by Thermo Fisher Scientific (1 mentions) 2 2 azobis 2 methylpropionitrile, by Merck Group (1 mentions) Dulbecco s modified eagle s medium dmem, by American Type Culture Collection (1 mentions) Alexa fluor 488 tetrafluorophenyl ester, by Thermo Fisher Scientific (1 mentions) Phalloidin conjugated to alexa flour 594, by Thermo Fisher Scientific (1 mentions) Deuterated dmso dmso d6, by Cambridge Isotopes (1 mentions) Vectashield mounting medium with dapi, by Vector Laboratories (1 mentions)

7 protocols using anhydrous dioxane

1

Hydrophilic Solvent Purification Protocols

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All reactions were carried out under an atmosphere of dry nitrogen. Anhydrous dioxane, CPME, and toluene were purchased from Sigma-Aldrich and used without further purification. THF was dried through activated alumina columns. Unless otherwise stated, all reagents were commercially available and used without further purification. Flash chromatography was performed with silica gel (300–400 mesh). The NMR spectra were obtained using a Brüker 500 MHz Fourier-transform NMR spectrometer. High-resolution mass spectrometry (HRMS) data were obtained on a Waters LC-TOF mass spectrometer (model LCT-XE Premier) using chemical ionization (CI) or electrospray ionization (ESI) in positive or negative mode, depending on the analyte.
Zheng B., Li M., Gao G., He Y, & Walsh P.J. (2016). Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides. Advanced synthesis & catalysis, 358(13), 2156-2162.
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2

Synthesis of N,N-diethylacetamide under Inert Conditions

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All reactions were conducted under an inert atmosphere of dry nitrogen. Anhydrous dioxane, CPME, and 2-MeTHF were purchased from Sigma-Aldrich and used without further purification. Dichloromethane and toluene were dried through activated alumina columns under nitrogen. Unless otherwise stated, reagents were commercially available and used as received without further purification. Chemicals were purchased from Sigma-Aldrich, Acros, or Matrix Scientific and solvents were obtained from Fisher Scientific. Flash chromatography was performed with Silica gel (230–400 mesh, Silicycle). NMR spectra were obtained using a Brüker 500 MHz Fourier-transform NMR spectrometer. The infrared spectra were obtained with KBr plates using a Perkin-Elmer Spectrum 1600 Series spectrometer. High resolution mass spectrometry (HRMS) data were obtained on a Waters LC-TOF mass spectrometer (model LCT-XE Premier) using chemical ionization (CI) or electrospray ionization (ESI) in positive or negative mode, depending on the analyte. Melting points were determined on a Unimelt Thomas-Hoover melting point apparatus and are uncorrected. N,N-diethylacetamide was purchased from Sigma-Aldrich and stored under nitrogen.
Zheng B., Jia T, & Walsh P.J. (2014). A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides. Advanced synthesis & catalysis, 356(1), 165-178.
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3

Synthesis and Characterization of Lactide-Glycolide Copolymer

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3,6-Dimethyl-1,4-dioxane-2,5-dione (lactide, 95%) and 1,4-dioxane-2,5-dione (glycolide, 97%) were purchased from BLDpharm (BLD Pharmatech Ltd., Shanghai, China). Tin (II) 2-ethylhexanoate (92.5–100%), tartrazine trisodium salt (95%), anhydrous dioxane and CDCl3 were obtained from Sigma-Aldrich, St. Louis, MO, USA. Alendronate sodium trihydrate (ALN·3H2O), fluorescamine (>98%) and EDTA were obtained from Carbosynth Ltd., Berkshire, United Kingdom. Methanol, dichloromethane (DCM), tetrahydrofuran (THF), acetonitrile (ACN) and 1-octanol were purchased from ChemSupply, Gillman, Australia. GPC PEG standards were purchased from PSS Polymer Standards Service GmbH, Mainz, Germany. Natureworks 4043D PLA pellets (Mw(GPC) = 200 kDa) were purchased from Filabot, Barre, VT, USA. All chemicals were used as received unless otherwise specified.
Dharmayanti C., Gillam T.A., Williams D.B, & Blencowe A. (2020). Drug-Eluting Biodegradable Implants for the Sustained Release of Bisphosphonates. Polymers, 12(12), 2930.
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4

Polymer Synthesis and Protein Labeling

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Triethylene glycol monomethyl ether (mTEG), 1,8-diazabicylo[5.4.0]undec-7-ene (DBU), 2,2′-azobis(2-methylpropionitrile) (AIBN), 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid (DDMAT), ovotransferrin (OTF), 4-iodoanisole, and anhydrous dioxane were purchased from Sigma-Aldrich and used without further purification unless otherwise noted. The monomer 2-vinyl-4,4-dimethylazlactone (VDMA) was synthesized as previously described.69 Fluorescein cadaverine (FC) was purchased from Biotium. Alexa Fluor 488 tetrafluorophenyl ester, NuPAGE 4–12% Bis-Tris gels, MES buffer, and LDS buffer were purchased from ThermoFisher Scientific. Inhibitor removal resin was purchased from Alfa Aesar. Holo-transferrin (HTf, Cat. No. 616397) was purchased from CalBiochem. PBS (10×) was purchased from Fisher Scientific. THF was purified using alumina drying columns. All other solvents were purchased from Pharmco-AAPER (Brookfield, CT). Deuterated DMSO (DMSO-d6) and deuterated chloroform (CDCl3) were purchased from Cambridge Isotope Laboratories, Inc. Dulbecco’s Modified Eagle’s Medium (DMEM) was purchased from ATCC, and all other cell culture reagents were obtained from Gibco. Phalloidin conjugated to Alexa Flour 594 was purchased from Thermo Fisher, formaldehyde as a 3.7% solution in PBS was from Fisher Scientific, and Vectashield mounting medium with DAPI was from Vector Labs.
Kim J.S., Sirois A.R., Cegla A.J., Jumai’an E., Murata N., Buck M.E, & Moore S.J. (2019). Protein–Polymer Conjugates Synthesized Using Water-Soluble Azlactone-Functionalized Polymers Enable Receptor-Specific Cellular Uptake toward Targeted Drug Delivery. Bioconjugate chemistry, 30(4), 1220-1231.
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5

Anhydrous Solvent Handling and NMR Analysis

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All air- and moisture-sensitive reactions were conducted under a dry nitrogen atmosphere in oven-dried glassware, using standard syringe/cannula transfer techniques unless otherwise reported. Anhydrous dioxane (Sigma Aldrich) was used directly from a Sure/Seal bottle. Unless otherwise stated, all commercial reagents were purchased from Sigma Aldrich and used without further purification. 1H NMR spectra were recorded on a Bruker 400 MHz spectrometer in either CDCl3 or DMSO-d6. Chemical shifts (δ) are reported in parts per million (ppm) after calibration to the internal reference solvent peak (CDCl3: 7.26 ppm and DMSO-d6: 2.50 ppm). Coupling constants (J) are reported in Hz. Exact mass was calculated for M+Na using electrospray ionization unless reported otherwise. Using a Hewlett Packard 8453 UV-Vis spectrophotometer, solubility was obtained either by measuring the increase in light scatter upon increasing precipitation via absorbance at 700 nm, or by using absorbance calibration curves at the noted wavelength and then extrapolating concentration from saturated sample absorbance [33 (link)].
Lewis T.R., Smith J., Griffin K., Aguiar S., Rueb K.F., Holmberg-Douglas N., Sampson E.M., Tomasetti S., Rodriguez S., Stachura D.L, & Arpin C.C. (2020). NHD2-15, a novel antagonist of Growth Factor Receptor-Bound Protein-2 (GRB2), inhibits leukemic proliferation. PLoS ONE, 15(8), e0236839.
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6

Lignin Modification Protocol

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Dimethyl sulfate (DMS), sodium
hydroxide (NaOH), sulfuric acid (95.0–98.0%), anhydrous methanol
(99.8%), anhydrous dioxane (99.8%), p-toluene sulfonic
acid, sodium borohydride (NaBH4), ethanol (99.9%), acetone
(≥99.5%), hydrochloric acid (HCl), acetic anhydride, deuterated
chloroform (CDCl3), pyridine, deuterated dimethyl sulfoxide
(DMSO-d6), endo-n-hydroxy-5-norbornene-2,3-dicarboximide
(e-HNDI), chromium(III) acetylacetonate (Cr(acac)3), and
2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (TMDP; all analytical
grades) were purchased from Sigma-Aldrich. 1,1-Diphenyl-2-picrylhydrazyl
stable radical was purchased from Thermo Fisher. Softwood Kraft lignin
(Indulin AT) is a commercially available technical lignin. Prior to
conducting the experiments, Indulin AT (Ind-AT) was dried under a
vacuum overnight with the aid of P2O5. Modifications
of the lignin were carried out using reported protocols.34 ,37 (link)
Diment D., Tkachenko O., Schlee P., Kohlhuber N., Potthast A., Budnyak T.M., Rigo D, & Balakshin M. (2023). Study toward a More Reliable Approach to Elucidate the Lignin Structure–Property–Performance Correlation. Biomacromolecules, 25(1), 200-212.
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7

Synthesis of Terpolymer-Based Nanoparticles

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α-tocopherol (Sigma-Aldrich, Saint Louis, MO, USA), methacryloyl chloride (Sigma-Aldrich, Saint Louis, MO, USA), triethylamine (Scharlau, Barcelona, Spain), tetrabutylammonium iodide (Sigma-Aldrich, Saint Louis, MO, USA), dichloromethane (Sigma-Aldrich, Saint Louis, MO, USA), hexane (Sigma-Aldrich, Saint Louis, MO, USA), hydrochloric acid (VWR, Rochester, NY, USA), sodium hydroxide (Sigma-Aldrich, Saint Louis, MO, USA), 1,4-dioxane (Panreac, Barcelona, Spain), anhydrous dioxane (Sigma-Aldrich, Saint Louis, MO, USA), N-vinylcaprolactam (VC, Sigma-Aldrich), 1-vinyl-2-pyrrolidone (VP, Sigma-Aldrich) and 2,2′-azobisisobutyronitrile (AIBN, Sigma-Aldrich) were used for the preparation of a terpolymer (poly(MVE-co-VP-co-VC)), as described in a previous work [40 (link)].
Celecoxib (CLX, Sigma-Aldrich), dexamethasone (DEX, Sigma-Aldrich), tenoxicam (TNX, Alfa Aesar, Kandel, Germany) and ethanol (VWR, Matsonford Road, Radnor, PA, USA) were used as received for the synthesis of the NPs. Sodium chloride (NaCl, Sigma-Aldrich, Saint Louis, MO, USA) and sodium phosphate dibasic (Na2HPO4, Sigma-Aldrich, Saint Louis, MO, USA) were used for the preparation of a phosphate buffered saline (PBS) solution in which NPs were synthesized and diluted.
Pontes-Quero G.M., Benito-Garzón L., Pérez Cano J., Aguilar M.R, & Vázquez-Lasa B. (2021). Modulation of Inflammatory Mediators by Polymeric Nanoparticles Loaded with Anti-Inflammatory Drugs. Pharmaceutics, 13(2), 290.
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