morpholin-3-one Chemical Properties

Melting point:

103.0 to 107.0 °C

Boiling point:

142°C/7mmHg(lit.)

Density 

1.122±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

14.37±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C4H7NO2/c6-4-3-7-2-1-5-4/h1-3H2,(H,5,6)

InChIKey

VSEAAEQOQBMPQF-UHFFFAOYSA-N

SMILES

N1CCOCC1=O

CAS DataBase Reference

109-11-5(CAS DataBase Reference)

EPA Substance Registry System

3-Morpholinone (109-11-5)

Safety Information

Safety Statements 

24/25

HS Code 

29349990

morpholin-3-one Usage And Synthesis

Description

3-ketomorpholine is also known as morpholin-3-one. It is useful pharmacological intermediate. Recent studies have shown that some morpholin-3-one derivatives could effectively cause cell cycle arrest at G1 phase, increase the levels of P53 and Fas, and induce A549 cell apoptosis in lung cancer. This indicates it might be a useful tool for elucidating the molecular mechanism of lung cancer cell apoptosis and might also be potential anti-cancer drugs. Some of its derivatives have been proven to be useful for the prevention and treatment of arteriosclerosis and hypertriglyceridemia.

Uses

3-Morpholinone is used as a reactant in the synthesis of 3-Morpholinone derivates. An example of this is 4-(4-Aminophenyl)-3-morpholinone, the key intermediate in the synthesis of Rivaroxaban (an anticoagulant).

Synthesis

To a solution of 2-aminoethanol (197 mmol, 1.1 eq.) in isopropanol (100 mL) was added sodium metal (197 mmol, 1.1 eq.) in batches. The reaction mixture was heated and stirred at 50 °C for 5 h to give a yellow solution, which was subsequently cooled to 0 °C in an ice-water bath. Ethyl chloroacetate (179 mmol, 1.0 eq.) was added slowly and dropwise at 0 °C and the yellow suspension formed was heated and stirred at 80 °C for 2 hours. After completion of the reaction, insoluble impurities were removed by filtration through filter paper and the filtrate was washed with isopropanol. The filtrate and washings were combined and concentrated under reduced pressure to give a brown solid. Finally, the crude product was recrystallized using mixed isopropanol/ethyl acetate solvent to give 3-morpholinone in 52% yield.

References

He, Q., et al. "Novel morpholin-3-one derivatives induced apoptosis and elevated the level of P53 and Fas in A549 lung cancer cells." Bioorganic & Medicinal Chemistry 15.11(2007): 3889.
Murai, Hiromu, et al. "Morpholinone derivatives and method of use." US, US4237132. 1980.
Gonzalez-garcia, Maria Rosario, and Fernandez, Maria Carmen. "Morpholinyl derivatives useful as MOGAT-2 inhibitors." (2015).

morpholin-3-one(109-11-5)Related Product Information

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• 3-Morpholinone, 4-phenyl-
• 6-[4-(Trifluoromethyl)phenyl]morpholin-3-one,6-(α,α,α-Trifluoro-p-tolyl)morpholin-3-one
• thiomorpholin-3-one
• R-5-PHENYL-MORPHOLIN-2-ONE
• 4-METHYLBENZO[B]MORPHOLIN-3-ONE
• 5,6-Diphenyl-2-morpholinone
• BENZO[B]MORPHOLIN-3-ONE
• 5-MORPHOLINO-2-NITROPHENOL
• 5-Phenyl-2-morpholinone
• 4-(4-NITROPHENYL)MORPHOLIN-3-ONE
• lateritin
• 4-T-BOC-(5S)-5-[(1S)-METHYLPROPYL]-MORPHOLIN-3-ONE