2 ethyl 2 oxazoline etox

Manufactured by Merck Group

Sourced in United States

2-Ethyl-2-oxazoline (EtOx) is a cyclic imine compound. It is a colorless liquid with a boiling point of approximately 145°C. EtOx is used as a building block for the synthesis of various polymers and other chemical compounds.

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Lab products found in correlation

Porcine liver esterase, by Merck Group (2 mentions) Eosin b, by Merck Group (2 mentions) Methyl tosylate meots, by Merck Group (2 mentions) Lucirintpo l ethyl 2 4 6 trimethylbenzoylphenylphosphinate, by ABCR (2 mentions) Deuterated chloroform, by Merck Group (2 mentions) 2 2 ethylenedioxy diethanethiol deg dichloromethane, by Merck Group (2 mentions) Potassium phthalimide, by Merck Group (1 mentions) 2 5 dihydroxybenzoic acid dhb, by Merck Group (1 mentions) Barium oxide, by Thermo Fisher Scientific (1 mentions) Calcium hydride cah2, by Merck Group (1 mentions) 2 methyl 2 oxazoline meox, by Merck Group (1 mentions) Sodium trifluoroacetate natfa, by Merck Group (1 mentions) Triethylamine tea, by Merck Group (1 mentions) 1260 series hplc system, by Agilent Technologies (1 mentions) Avance 300 mhz spectrometer, by Bruker (1 mentions) Toluene, by Thermo Fisher Scientific (1 mentions) Pyridine, by Carl Roth (1 mentions) Tetramethylammonium hydroxide, by Thermo Fisher Scientific (1 mentions) Diethyl ether, by Carl Roth (1 mentions) Acetone, by Thermo Fisher Scientific (1 mentions)

Close spelling variants of this product

2-ethyl-2-oxazoline (5 citations)

6 protocols using 2 ethyl 2 oxazoline etox

Synthesis and Characterization of Degradable Oxazoline Polymers

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2-Ethyl-2-oxazoline (EtOx) and methyl tosylate (MeOTs) were purchased
from Sigma-Aldrich (Vienna, Austria), purified by distillation over sodium
sulfate and stored in inert atmosphere. 2,2′-(Ethylenedioxy)diethanethiol
(DEG), dichloromethane, ethanol and deuterated chloroform were acquired from
Sigma-Aldrich (Vienna, Austria) and used without purification. Glycol
dimercaptoacetate (GDMA) was kindly provided by Bruno Brock (Marschacht,
Germany) and used without any further purification. The photoinitiator Lucirin
TPO-L^®, ethyl-2,4,6-trimethylbenzoylphenylphosphinate, was
purchased from abcr GmbH (Karlsruhe, Germany). Deionized water was produced
through reverse osmosis. 2-But-3′-enyl-2-oxazoline (Bu⁼Ox),
2-nonyl-2-oxazoline (NonOx) and 2-dec-9′-enyl-2-oxazoline (Dc⁼Ox)
were synthesized according to literature protocols [22 –24 (link)],
purified by distillation and flash chromatography using chloroform as an eluent.
For the degradation studies, the enzymes (namely porcine liver esterase and
rabbit liver esterase), Eosin B, and the buffer solutions (pH = 4, 6, 8, and 10)
were acquired from Sigma-Aldrich (Vienna, Austria) and used as received.

Luef K.P., Petit C., Ottersböck B., Oreski G., Ehrenfeld F., Grassl B., Reynaud S, & Wiesbrock F. (2016). UV-mediated thiol-ene click reactions for the synthesis of drug-loadable and degradable gels based on copoly(2-oxazoline)s. European polymer journal, 88, 701-712.

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Synthesis and Characterization of Degradable Oxazoline Polymers

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Synthesis of Functionalized Polymers

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Barium oxide (BaO, 90%, ACROS), calcium hydride (CaH₂, Sigma-Aldrich), triethylamine (TEA, Sigma-Aldrich), potassium phthalimide (Sigma-Aldrich), hydrazine monohydrate (N₂H₂, 64 to 66% N₂H₄, Sigma-Aldrich), sodium trifluoroacetate (NaTFA, 98%, Sigma-Aldrich), 2,5-dihydroxybenzoic acid (DHB, 98%, Sigma-Aldrich) were used as purchased. Prior to use, 2-ethyl-2-oxazoline (EtOx, Sigma-Aldrich) and 2-methyl-2-oxazoline (MeOx, Sigma-Aldrich) were stirred over BaO overnight, distilled and stored under argon atmosphere. Methyl p-tosylate (MeTos, Sigma-Aldrich) was pre-dried over CaH₂, distilled under reduced pressure and stored under argon atmosphere. Acetonitrile was obtained from a solvent purification system (SPS; Pure solv EN, InnovativeTechnology). HPLC and MS grade acetonitrile and water for HPLC measurements were obtained from VWR. All other chemicals and solvents were received from common commercial sources and used without further purification unless otherwise stated.

Engel N., Dirauf M., Czaplewska J.A., Nischang I., Gottschaldt M, & Schubert U.S. (2024). Determination of ω-end functionalities in tailored poly(2-alkyl-2-oxazoline)s by liquid chromatography and mass spectrometry. Royal Society Open Science, 11(2), 231008.

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Synthesis and Characterization of Functional Polymers

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Materials. Acetonitrile and triethylamine (Aldrich) were dried in a solvent purification system (J. C. Meyer). 2-Ethyl-2-oxazoline (EtOx; Aldrich) was distilled over barium oxide and stored under argon. Methyl tosylate (MeOTs) was distilled and stored under argon. Piperazine was purified by sublimation and stored under argon. (1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate (BCN-PNP) was purchased from SynAffix and stored at -20°C. All other chemicals were purchased from Sigma-Aldrich or Acros Organics and used as received.
Instrumentation. Polymerizations were performed in a capped vial in a microwave reactor (Biotage Initiator Sixty) equipped with an IR temperature sensor. 1 H NMR spectra were recorded in CDCl 3 on a Bruker Avance 300 MHz spectrometer. Size-exclusion chromatography (SEC) was performed on a Agilent 1260-series HPLC system equipped with a 1260 online degasser, a 1260 ISO-pump, a 1260 automatic liquid sampler (ALS), a thermostatted column compartment (TCC) at 50°C equipped with two PLgel 5 µm mixed-D columns and a precolumn in series, a 1260 diode array detector (DAD) and a 1260 refractive index detector (RID) using N,Ndimethylacetamide containing 50 mM of LiCl (flow rate of 0.59 mL min -1 ) as solvent. Molar masses were calculated against polymethylmethacrylate standards.

Glassner M., Palmieri L., Monnery B.D., Verbrugghen T., Deleye S., Stroobants S., Staelens S., Wyffels L, & Hoogenboom R. (2017). The Label Matters: μPET Imaging of the Biodistribution of Low Molar Mass ⁸⁹Zr and ¹⁸F-Labeled Poly(2-ethyl-2-oxazoline). Biomacromolecules, 18(1).

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Synthesis and Characterization of Oxazoline Polymers

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Maleic anhydride (99%, Bernd Kraft), furan (99%, Acros), ethanolamine (99%, Acros), 4-toluenesulfonyl chloride (99%, Acros), 4-nitrobenzenesulfonyl chloride (97%, Sigma-Aldrich), pyridine (99%, Roth), tetramethylammonium hydroxide (25 wt% in methanol, Acros), bovine serum albumin (BSA; Sigma), toluene (Fisher), petroleum ether (Acros), ethanol (99.8%, Acros), acetone (Fisher), tetrahydrofuran (THF; VWR), diethyl ether (99.5%, Roth), and dichloromethane (DCM; VWR) were used as received. Acetonitrile (MeCN; Sigma-Aldrich) was dried in a solvent purification system (JC Meyer) before use as a polymerization solvent. 2-Ethyl-2-oxazoline (EtOx; Aldrich) was distilled over barium oxide and stored under argon.

Gil Alvaradejo G., Glassner M., Hoogenboom R, & Delaittre G. (2018). Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route: synthesis and (bio)conjugation. RSC Advances, 8(17), 9471-9479.

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Purification and Functionalization of Solvents

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Dichloromethane (DCM, 99.9%, Molar Chemicals, Halásztelek, Hungary), tetrahydrofuran (THF, 99.9%, VWR Chemicals, West Chester, PA, USA), benzotrifluoride (BTF, ≥99%, Sigma-Aldrich, St. Louis, MO, USA) and 2-ethyl-2-oxazoline (EtOx, 99+%, Aldrich, St. Louis, MO, USA) were refluxed on CaH₂ for a couple of hours and distilled over it under N₂ atmosphere freshly before use. Triethylamine (TEA, ≥99.0%, TCI Chemicals, Tokyo, Japan) and 1-methylimidazole (1-MI, ≥99%, Sigma-Aldrich, St. Louis, MO, USA) was distilled under N₂ atmosphere freshly before use. Glissopal 1000 (BASF SE, Ludwigshafen, Germany), p-toluenesulfonyl chloride (tosyl chloride, TsCl, ≥99.0%, TCI Chemicals, Tokyo, Japan), p-nitrobenzenesulfonyl chloride (nosyl chloride, NsCl, 97%, Sigma-Aldrich, St. Louis, MO, USA) and 4-dimethylaminopyridine (DMAP, ≥99.9%, Sigma-Aldrich, St. Louis, MO, USA) were used as receive.

Pásztói B., Trötschler T.M., Szabó Á., Szarka G., Kerscher B., Mülhaupt R, & Iván B. (2020). Synthesis of Tosyl- and Nosyl-Ended Polyisobutylenes with High Extent of Functionalities: The Effect of Reaction Conditions. Polymers, 12(11), 2504.

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