World Library  
Flag as Inappropriate
Email this Article


Article Id: WHEBN0006737874
Reproduction Date:

Title: Isoxazolidine  
Author: World Heritage Encyclopedia
Language: English
Subject: Heterocyclic compound
Publisher: World Heritage Encyclopedia


CAS number 504-76-7 YesY
Jmol-3D images Image 1
Molecular formula C3H7NO
Molar mass 73.0938 g/mol
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

An Oxazolidine is a five-membered ring compound consisting of three carbons, a nitrogen, and an oxygen. The oxygen and NH are the 1 and 3 positions, respectively. In oxazolidine derivatives, there is always a carbon between the oxygen and the nitrogen (or it would be an isoxazolidine).[1][2] All of the carbons in oxazolidines are reduced (compare to oxazole and oxazoline). Some of their derivatives, the oxazolidinediones, are used as anticonvulsants.


Bisoxazolidines are chemical compounds that contain two oxazolidine rings, they are used as performance modifiers in polyurethane coatings and paints. The rings hydrolyze in the presence of moisture to give amine and hydroxyl groups, these can then react with diisocyanates to form a coating.[3] The use of a bisoxazolidine in a polyurethane systems can prevent the unwanted reaction between isocyanate and moisture resulting in coating defects, a result of carbon dioxide release. This moisture triggered curing route is preferential to moisture cure.

The choice of linker between the two oxazolidine rings has a large impact on the performance when used to cure isocyanates. A rigid linker group increases a polyurethanes toughness. A flexible linker group imparts flexibility and increases elongation of a coating. These differences are the reason why bisoxazolidines are used to enhance the performance of polyurethane systems.


In an isoxazolidine nitrogen and oxygen occupy positions 1 and 2 in the ring:

It is the saturated relative of Isoxazole.

See also

  • Imidazole, an analog with the oxygen replaced by a nitrogen.
  • Thiazole, an analog with the oxygen replaced by a sulfur.
  • Benzoxazole, where the oxazole is fused to another aromatic ring.
  • Pyrrole, an analog without the oxygen atom.
  • Furan, an analog without the nitrogen atom.
  • Oxazoline, which has only one double bond reduced.
  • Oxazolidinedione, which has two in-cycle keto groups (a carbamate and a lactam).
  • Oxazolidinone, which has an in-cycle carbamate.


This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from World eBook Library are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.