Morpholin-3-one

Base Information

• Chemical Name: Morpholin-3-one
• CAS No.: 109-11-5
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• Hs Code.: 29349990
• European Community (EC) Number: 203-647-9
• NSC Number: 11688
• UNII: V6P29M33NG
• DSSTox Substance ID: DTXSID3074444
• Nikkaji Number: J193.575E
• Wikidata: Q72486957
• Mol file: 109-11-5.mol

Synonyms:Morpholin-3-one;109-11-5;3-Morpholinone;3-Ketomorpholine;morpholinone;MFCD00631009;V6P29M33NG;EINECS 203-647-9;NSC-11688;3-oxomorpholine;3-oxo-morpholine;NSC11688;UNII-V6P29M33NG;SCHEMBL77344;DTXSID3074444;3-Oxomorpholine;UPCMLD00WGW006:001;BCP21660;CS-D1427;STR09474;NSC 11688;AKOS005261878;PB29100;NCGC00165408-01;SY003974;AM20080044;BB 0261379;FT-0647730;M2788;EN300-98969;J-002233;J-522712;F8889-4140

Chemical Property of Morpholin-3-one

Chemical Property:

• Vapor Pressure: 0.000512mmHg at 25°C
• Melting Point: 104-106℃
• Refractive Index: 1.435
• Boiling Point: 313 °C at 760 mmHg
• PKA: 14.37±0.20(Predicted)
• Flash Point: 143.1 °C
• PSA: 38.33000
• Density: 1.122 g/cm³
• LogP: -0.53840
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 101.047678466
• Heavy Atom Count: 7
• Complexity: 81.8

Purity/Quality:

99.0%min ^*data from raw suppliers

3-Morpholinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCC(=O)N1
• 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.

Technology Process of Morpholin-3-one

There total 17 articles about Morpholin-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.6%

tert-butyl 2-(2-aminoethoxy)acetate (1155811-37-2) → morpholine-3-one (109-11-5)

Guidance literature:

With trifluoroacetic acid; In toluene; for 3h; Reflux; Large scale;

Reference yield: 94.0%

C4H8N4O2 (1366074-90-9) → morpholine-3-one (109-11-5)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; for 48h; Reflux;

DOI:10.5012/bkcs.2012.33.2.739

Reference yield: 75.5%

C4H8ClNO2 → morpholine-3-one (109-11-5)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol; at 80 - 85 ℃; for 12h; Reagent/catalyst; Temperature;

upstream raw materials:

2-chloroethyl cyanomethyl ether

potassium phtalimide

butyl glycolate

ethanolamine

Downstream raw materials:

4-methyltetrahydro-1,4-oxazin-3-one

2-(2-aminoethoxyl)acetic acid

1-cyclohexyl-2-{2-fluoro-4-[5-nitro-2-(3-oxomorpholin-4-yl)benzyloxy]phenyl}-1H-benzimidazole-5-carboxylic acid methyl ester

4-(4-nitrophenyl)-3-morpholinone

Refernces

Applications of Stevens [1,2]-shifts of cyclic ammonium ylides. A route to morpholin-2-ones

10.1021/jo00099a041

The study explores the synthesis of morpholin-2-ones via the Stevens [1,2]-shift mechanism. The researchers prepared 2-(N,N-dialkylamino)ethyl diazoacetoacetates (compounds 2) from readily available ethanolamines (compounds 1) in a two-step process. These diazoacetoacetates were then heated in the presence of catalytic copper to form morpholinones (compounds 3), presumably via the intermediacy of copper carbenoids and cyclic ammonium ylides. The study found that benzylic or allylic migrating groups typically underwent the [1,2]-shift in good yield (55-80%), while simple alkyl groups, except for tert-butyl, failed to rearrange. The study also investigated the use of different copper catalysts and their impact on the yield of the desired morpholinone products. The findings suggest that this method provides a straightforward route to morpholinones, which can serve as precursors to various amino acid derivatives, thus contributing to the development of synthetic methods for a-amino acids and their derivatives.