2-Ethyl-2-oxazoline

2-Ethyl-2-oxazoline structure01.svg 150px 2-Ethyl-4,5-dihydro-1,3-oxazole 2-Ethyloxazoline 10431-98-8 correct CAS B8CD92T4P5 correct FDA 66412 CCC1=NCCO1 59786 1S/C5H9NO/c1-2-5-6-3-4-7-5/h2-4H2,1H3 NYEZZYQZRQDLEH-UHFFFAOYSA-N 5 9 1 1 0.982 g/mL http://www.sigmaaldrich.com/catalog/product/aldrich/137456?lang=en 2-Ethyl-2-oxazoline Sigma-Aldrich −62 128.4 2-Ethyl-2-oxazoline (EtOx) is an oxazoline which is used particularly as a monomer for the cationic ring-opening polymerization to poly(2-alkyloxazoline)s.T. Kagiya S. Narisawa T. Maeda K. Fukui J. Polym. Chem., Polym. Lett. Ring-opening polymerization of 2-substituted 2-oxazolines 4 7 441–445 10.1002/pol.1966.110040701 1966 This type of polymers are under investigation as readily water-soluble and biocompatible materials for biomedical applications.R. Hoogenboom Angew. Chem. Int. Ed. Poly(2-oxazoline)s: A polymer class with numerous potential applications 48 43 7978–7994 10.1002/anie.200901607 19768817 2009 Production From propionic acid and derivatives Carboxylic acids, carboxylic esters, carboxylic amides and nitriles can react with 2-amino alcohols at 200 °C upon dehydration to the corresponding N-(2-hydroxy)carbamide, which react further at 260–280 °C upon dehydration to the 2-alkyl-2-oxazoline. 350px|center|Synthese von 2-Ethyl-2-oxazolin aus Carbonsäurederivaten For example, N-(2-hydroxyethyl)propionamide is first formed from propionic acid and ethanolamine in 74% yield which can be dehydrated to give 2-ethyl-2-oxazoline in about 75% yield.H. Wenker J. Am. Chem. Soc. The synthesis of Δ2-oxazolines and Δ2-thiazolines from N-acyl-2-aminoethanols 57 6 1079–1080 10.1021/ja01309a034 1935 600px|center|Synthese von 2-Ethyl-2-oxazolin über N-(2-Hydroxyethyl)propionamid Less drastic reaction conditions require the dehydration of the N-(2-hydroxyethyl)propionamide in vacuo in the presence of iron(III)chloride, which delivers the product in 90% yield. US 4203900 Process for preparing 2-oxazolines 1980-05-20 1977-01-03 M.E. Kaiser The Dow Chemical Co. An even higher yield of 96.2% is obtained by heating with zinc acetate. US 4354029 Preparation of 2-substituted 2-oxazolines with organic zinc salt catalysts 1982-10-12 1981-11-30 M.E. Kaiser, D.L. Larson The Dow Chemical Co. An economic one-pot reaction is heating the salt of propionic acid with ethanolamine at 200 °C in vacuo in the presence of zinc chloride yielding 82% 2-ethyl-2-oxazoline. From the water-containing distillate pure 2-ethyl-2-oxazoline can be isolated by extraction with diethylbenzene and subsequent distillation or by distillation only after addition of diethyl phosphite or dimethyldichlorosilane. The product can be dried to a residual water content of 10 ppm. US 4281137 Purification of 2-oxazolines 1981-07-28 1980-02-20 J.W. Sanner, P.W. Owen The Dow Chemical Co. In another one-pot reaction propionic acid is converted first with 2-aminoethanol to 2-hydroxyethylamide, than reacted with boric acid at 130 °C yielding a boric acid ester which is finally thermolyzed at 280 °C in 92% yield to 2-ethyl-2-oxazoline.B. Ilkgul D. Gunes O. Sirkecioglu N. Bicak Tetrahedron Lett. Synthesis of 2-oxazolines via boron esters of N-(2-hydroxyethyl) amides 2010 51 40 5313–5315 10.1016/j.tetlet.2010.07.167 600px|center|Synthese von 2-Ethyl-2-oxazolin über Boratester From propionic acid and thionyl chloride can be obtained propanoyl chloride, which reacts with ethanolamine in the presence of an acid scavenger (for example pyridine) to N-propionyl-2-aminoethanol. With further thionyl chloride this reacts further to 2-chloroethylamide. With the chloride ion as a better leaving group, this intermediate is cyclized by simple heating to the oxazoline. Water must be excluded due to the tendency of oxazolines towards ring-opening by chloride ions during protonation of the imine nitrogen.M.N. Holerca V. Percec Eur. J. Org. Chem. 1H NMR Spectroscopic Investigation of the Mechanism of 2-Substituted-2-Oxazoline Ring Formation and of the Hydrolysis of the Corresponding Oxazolinium Salts 2000 12 2257–2263 10.1002/1099-0690(200006)2000:12<2257::AID-EJOC2257>3.0.CO;2-2 2000 600px|center|Synthese von 2-Ethyl-2-oxazolin über Propionsäureäurechlorid The direct reaction of propanoyl chloride with 2-chloroethylamine hydrochloride in the presence of triethylamine avoids the formation of water. 600px|center|Synthese von 2-Ethyl-2-oxazolin mit Chlorethylamin From propanal Propanal reacts with 2-aminoethanol in t-butanol to 2-ethyl-2-oxazoline in the presence of the iodinating reagent 1,3-diiodo-5,5-dimethylhydantoin (DIH) and potassium carbonate.S. Takahashi H. Togo Synthesis An Efficient Oxidative Conversion of Aldehydes into 2-Substituted 2-Oxazolines Using 1,3-Diiodo-5,5-dimethylhydantoin 2009 2329–2332 10.1055/s-0029-1216843 14 2009 400px|center|Synthese von 2-Ethyl-2-oxazolin aus Propionaldehyd Properties 2-Ethyl-2-oxazoline is a readily water-soluble, colorless liquid which is also soluble in a variety of organic solvents and possesses an amine-like smell.B23287 2-Ethyl-2-oxazoline 5. Juni 2016 Aqueous solutions react alkaline. The compound is stable in alkaline but hydrolyses under acid action. Applications In anhydrous form, 2-ethyl-2-oxazoline is mostly used as a monomer. The cationic ring-opening polymerization of 2-ethyl-2-oxazolineB.L. Rivas S.I. Ananias Polym. Bull. Ring-opening polymerization of 2-ethyl-2-oxazoline 18 3 189–194 10.1007/BF00255109 1987 94946485 can be initiated by alkylation with e.g. methyl tosylate or triflates (in particular methyl triflate) and leads to the water-soluble poly(2-ethyl-2-oxazoline) which is a propionyl-substituted linear polyethylenimine and can also be seen as a pseudo-polypeptide.H. Schlaad R. Hoogenboom Macromol. Chem. Rapid Commun. Poly(2-oxazoline)s and Related Pseudo-Polypeptides 33 19 1599 10.1002/marc.201200571 2012 22965791 free 550px|center|Kationische lebende Polymerisation von 2-Ethyl-2-oxazolin The polymerization of 2-ethyl-2-oxazoline can also be carried out as living cationic polymerization.Guerrero-Sanchez Carlos Hoogenboom Richard Schubert Ulrich S. 2006 Fast and “green” living cationic ring opening polymerization of 2-ethyl-2-oxazoline in ionic liquids under microwave irradiation http://xlink.rsc.org/?DOI=B608364A Chem. Commun. en 36 36 3797–3799 10.1039/B608364A 1359-7345 16969461 subscription Copolymers with other 2-alkyl-2-oxazolinesGlassner Mathias Lava Kathleen de la Rosa Victor R. Hoogenboom Richard November 2014 Tuning the LCST of poly(2‐cyclopropyl‐2‐oxazoline) via gradient copolymerization with 2‐ethyl‐2‐oxazoline https://onlinelibrary.wiley.com/doi/10.1002/pola.27364 Journal of Polymer Science Part A: Polymer Chemistry en 52 21 3118–3122 10.1002/pola.27364 0887-624X subscription and other monomersMotokucho Suguru Furukawa Mutsuhisa Kawashima Masahiro Kojio Ken Yoshinaga Kohji November 2013 Physical properties of poly(tetrahydrofuran)-block-poly(2-ethyl-2-oxazoline) triblock copolymer https://www.nature.com/articles/pj201339 Polymer Journal en 45 11 1115–1119 10.1038/pj.2013.39 0032-3896 free 10069/40210 free allow the preparation of random copolymers and block copolymers. The copolymers obtained can be used as biocompatible drug carriers,de la Rosa Victor R. May 2014 Poly(2-oxazoline)s as materials for biomedical applications http://link.springer.com/10.1007/s10856-013-5034-y Journal of Materials Science: Materials in Medicine en 25 5 1211–1225 10.1007/s10856-013-5034-y 0957-4530 23975334 1766066 subscription in coatings and adhesives, and in many other applications.Etox, 2-Ethyl-2-Oxazoline, Product Information Sheet Polymer Chemistry Innovations, Inc. https://www.polychemistry.com/etox/ 2016-07-19 The elimination of the propionyl group from poly (2-ethyl-2-oxazoline) yields linear polyethyleneimine. US 20100197888 Method for manufacturing linear polyethyleneimine (PEI) for transfection purpose and linear PEI obtained with such method 2010-08-05 2008-07-31 A. Adib, F. Stock, P. Erbacher Polyplus TransfectionLambermont-Thijs Hanneke M. L. van der Woerdt Friso S. Baumgaertel Anja Bonami Lies Du Prez Filip E. Schubert Ulrich S. Hoogenboom Richard 2010-01-26 Linear Poly(ethylene imine)s by Acidic Hydrolysis of Poly(2-oxazoline)s: Kinetic Screening, Thermal Properties, and Temperature-Induced Solubility Transitions https://pubs.acs.org/doi/10.1021/ma9020455 Macromolecules en 43 2 927–933 10.1021/ma9020455 0024-9297 subscription 400px|center|Herstellung von Linearem Polyethylenimin aus Poly(2-ethyloxazolin) References Category:Imines Category:Oxazolines