2 2 ethylenedioxy bis ethylamine

Manufactured by Merck Group

Sourced in United States, France

2,2'-(ethylenedioxy)bis(ethylamine) is a chemical compound used in various laboratory applications. It serves as a versatile reagent and building block for the synthesis of other compounds. The core function of this product is to provide a source of the ethylenedioxy and ethylamine moieties for chemical reactions and formulations.

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Ethylamine (20 citations)

8 protocols using 2 2 ethylenedioxy bis ethylamine

Graphene Oxide Synthesis and Characterization

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GO was synthesized following a modified Hummers’ method (Morimoto et al., 2016 (link)) and obtained as an aqueous dispersion with a concentration of 3 mg/mL. The solvents were obtained from commercial suppliers and used without purification. Water was purified using a Millipore MilliQ^® filter system equipped with the free endotoxin Polisseur Biopak. When stated, the suspensions were sonicated in a water bath Elmasonic P sonicator with settings at 20 W and 40 kHz. MWCO 12,000-14,000 Da dialysis membranes were purchased from Spectrum Laboratories, Inc. Polymyxin B sulfate salt (mixture of polymyxin B1 and B2) and 2,2′-(ethylenedioxy)bis(ethylamine) were purchased from Sigma Aldrich. Depending on the types of containers employed, either 50 mL conical tubes or 1.5 mL microtubes, two centrifuges (Eppendorf Centrifuge 5804R or Eppendorf Centrifuge 5415R) were used.

Pandit S., Jacquemin L., Zhang J., Gao Z., Nishina Y., Meyer R.L., Mijakovic I., Bianco A, & Pang C. (2023). Polymyxin B complexation enhances the antimicrobial potential of graphene oxide. Frontiers in Cellular and Infection Microbiology, 13, 1209563.

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Synthesizing Poly(epoxide-valerolactone) Nanoparticles

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Poly(α-allyl-valerolactone, valerolactone) containing 4% allyl groups was epoxidized with meta-chloroperoxybenzoic acid (mcpba, 1.2 eq per alkene, Sigma) in CH₂Cl₂ (0.065 M alkene) for 48 hours and washed with saturated sodium bicarbonate (15 ). The resulting polymer was dried under reduced pressure. 2,2′-ethylenedioxy-bis(ethylamine) (7.5 μL, 0.51 mmol, Sigma) was added to a solution of poly(epoxide-valerolactone, valerolactone) (0.173 g, M_n = 3,644 Da) dissolved in CH₂Cl₂ (21.1 mL). The reaction mixture refluxed for 12 hours at 46° C. Residual bisamine was removed by dialyzing with Snakeskin Pleated Dialysis Tubing (MWCO = 10,000) against CH₂Cl₂ to yield nanoparticles (NP).

de la Croix Ndong J., Stevens D.M., Vignaux G., Uppuganti S., Perrien D.S., Yang X., Nyman J.S., Harth E, & Elefteriou F. (2015). Combined MEK inhibition and BMP2 treatment promotes osteoblast differentiation and bone healing in Nf1Osx−/− mice. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 30(1), 55-63.

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Targeted Quantum Dot Conjugates for Imaging

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Poly(D,L-lactide-co-glycolide) (Resomer^® RG 504 H, 50:50 lactide:glycolide, acid terminal, MW 38.000–54.000 g/mol); Poly-vinyl alcohol (PVA, MW 9.000–10.000 g/mol, 80% hydrolyzed); N,N’-dicyclohexylcarbodiimide (DCC, MW 206.33 g/mol, 99%); Dimethylamino pyridine (DMAP, MW 122.17 g/mol, 99%); N,N-Diisopropylethylamine (DIPEA, 129.24 g/mol); Ninhydrin (MW 178.14 g/mol); Ethanolamine (MW 61.08 g/mol, ≥98%); N,N-Dimethylformamide (DMF, anhydrous ≥99.8%); 2,2 (Ethylenedioxy)bis(ethylamine) (EDBE, 98%); and Dimethyl sulfoxide 148.20 g/mol (DMSO, ≥ 99.9%) were purchased from Sigma-Aldrich Co. (St Louis, MO, USA). Quantum Dot 800 ITK (QDs, Invitrogen) were obtained from Thermo Fisher Scientific. Chloroform (≥99.8%) was purchased from Honeywell Riedel-de-Haën™ (Germany). ɑ-Maleinimidohexanoic-ω-NHS PEG (Malhex-NH-PEG-O-C₃H₆-CONHS, PEG-Mal, 3000 Da) was obtained from Rapp Polymer GmbH, Germany. Anti-MAdCAM1 antibody (AP-MAB0842, Rat Monoclonal, IgG2) was supplied by Abcam (Cambridge, UK).

Truffi M., Sevieri M., Morelli L., Monieri M., Mazzucchelli S., Sorrentino L., Allevi R., Bonizzi A., Zerbi P., Marchini B., Longhi E., Sampietro G.M., Colombo F., Prosperi D., Colombo M, & Corsi F. (2020). Anti-MAdCAM-1-Conjugated Nanocarriers Delivering Quantum Dots Enable Specific Imaging of Inflammatory Bowel Disease. International Journal of Nanomedicine, 15, 8537-8552.

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Synthesis of Graphite-Based Nanomaterials

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Flake graphite was purchased from Barnwell. All solvents and analytical grade H₂SO₄ were purchased from Fisher Scientific (UK). All other chemicals including KMnO₄, NaNO₃, H₂O₂, 2,2′-(ethylenedioxy)bis(ethylamine), and DOTA were purchased from Sigma-Aldrich. 2-(4-isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA–NCS) was purchased from Macrocyclics. The filtration and dialysis membranes were purchased from Millipore and Spectrum Laboratories, Inc., respectively.

Jasim D.A., Ménard-Moyon C., Bégin D., Bianco A, & Kostarelos K. (2015). Tissue distribution and urinary excretion of intravenously administered chemically functionalized graphene oxide sheets †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc00114e. Chemical Science, 6(7), 3952-3964.

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Synthetic Procedures for Molecular Probes

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IrCl₃·3H₂O (99%, I111008), 2‐(2‐pyridyl) benzothiophene (97%, P121516), 2‐ethoxyethanol (>99%, E110822), β‐CD (98%, C104384) were purchased from Aladdin, 4,6‐dioxoheptanoic acid was purchased from Huateng Pharma Co., Ltd., 2,2’‐(ethylenedioxy)bis(ethylamine) and p‐toluene sulfonylchloride (p‐TsCl) were purchased from Sigma‐Aldrich, and Cy7‐NHS was purchased from GE healthcare. Other analytical grade chemicals, such as methanol, n‐hexane, diethyl ether, acetone, tetrahydrofuran (THF), and DMSO were purchased from Sinopharm Chemical Reagent Beijing, Co., Ltd. All chemicals mentioned above were used as received without any further purification.

Xiao P., Liu C., Ma T., Lu X., Jing L., Hou Y., Zhang P., Huang G, & Gao M. (2021). A Cyclodextrin‐Hosted Ir(III) Complex for Ratiometric Mapping of Tumor Hypoxia In Vivo. Advanced Science, 8(8), 2004044.

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Thermoset Polymer Synthesis and Characterization

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Vanillin
(V) (99%), ethylene carbonate (EC)
(98%), potassium carbonate (K₂CO₃) (≥99%), N,N-dimethylformamide (DMF) (≥99%),
methacrylic anhydride (MAA) (94%), ethylenediamine (ED) (≥99%),
2,2′-(ethylenedioxy)bis(ethylamine) (Dom) (>97%), phenylbis(2,4,6-trimethylbenzoyl)phosphine
oxide (BAPO) (97%), and deuterium dimethyl sulfoxide (DMSO-d₆) (99.9% atom % D) were purchased from Sigma-Aldrich
and used without any additional purification. 4-(Dimethylamino)pyridine
(DMAP) (≥99.0%, Fluka), magnesium sulfate (99%, VWR), sodium
bicarbonate (≥99%, Merck), sodium hydroxide (NaOH) (≥99%,
Fisher Scientific), ethyl acetate (EtOAc) (≥99%, VWR), dichloromethane
(DCM) (≥99%, Fisher Scientific), hydrochloric acid (HCl) (37%),
and acetone (≥99.5%, VWR) were all used as received. Sodium
lignosulfonate for the coating of the thermosets and 2,2-diphenyl-1-picrylhydrazyl
(DPPH°) for the antioxidant assay were acquired from Tokyo Chemical
Industry Co., Ltd.

Liguori A., Xu H., Hazarika D, & Hakkarainen M. (2023). Simple Non-Equilibrium Atmospheric Plasma Post-Treatment Strategy for Surface Coating of Digital Light Processed 3D-Printed Vanillin-Based Schiff-Base Thermosets. ACS Applied Polymer Materials, 5(10), 8506-8517.

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Synthesis of Metal-Organic Complexes

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All the chemicals used were analytical reagent grade (AR) and of the highest purity. The chemicals used were imidazole-2-carboxaldehyde (Sigma-Aldrich), 2,2-(ethylenedioxy)bis(ethylamine) (Sigma-Aldrich), CrCl₃·6H₂O, MnCl₂·4H₂O, and FeCl₃·6H₂O (Sigma-Aldrich), CoCl₂·6H₂O, NiCl₂·6H₂O, CuCl₂·2H₂O, and CdCl₂ (Merck). Ethyl alcohol (95%) and N,N-dimethylformamide were used as organic solvents (DMF). In all the preparations, double-distilled water was widely used.

Ahmed Y.M., Omar M.M, & Mohamed G.G. (2021). Synthesis, spectroscopic characterization, and thermal studies of novel Schiff base complexes: theoretical simulation studies on coronavirus (COVID-19) using molecular docking. Journal of the Iranian Chemical Society, 19(3), 901-919.

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Graphite-Based Oxidation and Reduction Assays

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Graphite powder (size < 150 µm, 99.99%, Sigma, Saint-Quentin Fallavier, France), potassium permanganate KMnO₄ (>99%, Sigma), hydrogen peroxide H₂O₂ (30%, VWR Chemicals, Briare, France), sodium nitrate NaNO₃ (>99%, Sigma), sulfuric acid H₂SO₄ (reagent grade), 2,2’-(ethylenedioxy)bis(ethylamine) (98%, Sigma), ferrous chloride FeCl₂ (99.9%, Sigma), ferrozine (>99%, Sigma), potassium ferricyanide K₃Fe(CN)₆ (>99%, Sigma), ethylenediaminetetraacetic acid (EDTA) (>99%, Sigma), L-carnosine (99%, Sigma), murexide (ACS reagent, Sigma), copper sulphate CuSO₄ (>99%, Sigma), Trolox^® (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, >98%, Sigma), potassium persulfate K₂S₂O₈ (>99%, Sigma), trichloroacetic acid (>99%, ThermoFisher Scientific, Illkirch-Graffenstaden, France), and 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) (99%, Sigma) were used as received without further purification. All of the solutions were prepared while using Milli-Q water (18.2 MΩ.cm, Millipore) as solvent.

El-Hnayn R., Canabady-Rochelle L., Desmarets C., Balan L., Rinnert H., Joubert O., Medjahdi G., Ben Ouada H, & Schneider R. (2020). One-Step Synthesis of Diamine-Functionalized Graphene Quantum Dots from Graphene Oxide and Their Chelating and Antioxidant Activities. Nanomaterials, 10(1), 104.

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