Oxazolidine

Structural formula
General
Surname	Oxazolidine
other names	Oxazolane 1,3-oxazolidine ( IUPAC )
Molecular formula	C 3 H 7 NO
External identifiers / databases
CAS number 504-76-7 EC number 610-533-6 ECHA InfoCard 100.127.875 PubChem 536683 ChemSpider 467457 Wikidata Q417695
properties
Molar mass	73.09 g mol −1
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-314 P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxazolidine , formerly also called oxazolane , is a chemical compound . The heterocyclic compound is a hydrogenation product of the oxazole and the basic structure of the group of oxazolidines . A structurally isomeric compound is 1,2-oxazolidine (isoxazolidine).

Occurrence and representation

In nature there are many derivatives of oxazolidine, mostly as oxazolidinones ; the parent compound oxazolidine itself has not yet been found.

The oxazolanes can be obtained by reducing oxazoles with alcohols and sodium . They can also be produced by reacting β- amino alcohols with aldehydes . So formed, on reaction of formaldehyde that used as an industrial biocide with 2-amino-2-methylpropanol 4,4-dimethyloxazolidine .

use

In the past, derivatives of oxazolidine, namely oxazolidine-2,4-diones such as paramethadione and trimethadione, were used as anti- epileptic drugs ; Due to the relatively high toxicity ( trimethadione embryopathy ) and the necessary high doses, its use has now been discontinued. Oxazolidinediones act on the synapses by extending their refractory period.

Oxazolidines are currently used as microbicides in lubricants . They work by splitting off formaldehyde when heated , which kills bacteria and fungi .

Oxazolidines are also used as so-called latent hardeners in moisture-curing polyurethane systems. Amino alcohols are released through hydrolysis , which react with isocyanates with polyaddition to form urethane and urea groups.

Web links

• Entry for oxazolidine in the ChemIDplus database of the United States National Library of Medicine (NLM)

Individual evidence

1. ↑ There is not yet a harmonized classification for this substance . A labeling of 1,3-oxazolidine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on May 25, 2020, is reproduced from a self-classification by the distributor .
2. ↑ External identifiers or database links for 1,2-oxazolidine : CAS number: 504-72-3, PubChem : 136333 , ChemSpider : 120107 , Wikidata : Q27122030 .
3. ↑ JJ Florio, DJ Miller, LJ Calbo: Handbook of coatings additives. 2nd edition, CRC Press, 2004, ISBN 978-0-8247-5626-0 , pp. 273-274.
4. ^ Wissenschaft-Online-Lexika: Entry on "Oxazolidin-Derivate" in the Lexikon der Neurologie , accessed May 10, 2008.
5. ^ UJ Möller, J. Nassar: Lubricants in operation , Springer-Verlag , 2002, ISBN 3-540-41909-8 .
6. ↑ Kittel: Textbook of lacquers and coatings , 2nd edition, Volume 2: Binder for solvent-based and solvent-free systems, Ed. Walter Krauß, s. Hirzel Verlag 1998, ISBN 3-7776-0886-6 .