136476-53-4

Basic information

• Product Name: 5,5-dimethyl-4-ethyl-2-oxomorpholine
• Synonyms: 5,5-dimethyl-4-ethyl-2-oxomorpholine
• CAS NO: 136476-53-4
• Molecular Weight: 157.213
• Mol File: 136476-53-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5,5-dimethyl-4-ethyl-2-oxomorpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-4-ethyl-2-oxomorpholine(136476-53-4)
• EPA Substance Registry System: 5,5-dimethyl-4-ethyl-2-oxomorpholine(136476-53-4)

Safety Data

• Hazardous Substances Data: 136476-53-4(Hazardous Substances Data)

Upstream product

• 26985-31-9 methyl viologen cation radical 
• 143984-03-6 5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl 

Relevant articles and documents

Equilibrium between 2-oxomorpholin-3-yl radicals and viologen radicals. Determination of reduction potentials

Bi(3,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3 dimer) undergoes bond homolysis to yield 3,5,5-trimethyl-2-oxomorpholin-3-yl (TM-3), which reduces propyldiquat (PDQ2+) to its radical cation PDQ+. The byproduct is 5,6-dihydro-3,5,5-trimethyl-1,4-oxazin-2-one (8). Similarly, bi(5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl) (DEM-3 dimer) cleaves to 5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl (DEM-3), which reduces paraquat (PQ2+) to its radical cation PQ+. The byproduct, 5,5-dimethyl-4-ethyl-3-methoxy-2-oxomorpholine (10), results from rapid addition of methanol solvent to the transient 5,6-dihydro-4-ethyl-5,5-dimethyl-1,4-oxazin-2-onium cation (11). Concentration versus time data for the respective viologen radical cations together with reduction potentials for the viologens place the reduction potentials for TM-3 dimer and DEM-3 dimer at -0.56 and -0.33 V versus NHE, respectively, in Tris/Tris·H+ buffered methanol. The kinetics of reduction are analyzed using numerical integration, and the two reducing agents are compared with dithionite.