4-Methylmorpholine N-oxide
[CAS# 7529-22-8]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: 4-Methylmorpholine N-oxide
• Synonyms: N-Methyl morpholine-N-oxide; NMO
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 117.15
• CAS Registry Number: 7529-22-8
• EC Number: 231-391-8
• SMILES: C[N+]1(CCOCC1)[O-]

Properties

• Density: 1.14 g/mL
• Melting point: -20 °C
• Boiling point: 118-119 °C

Safety Data

• Hazard Symbols: GHS02;GHS03;GHS07;GHS08 Danger
• Risk Statements: H228-H272-H315-H319-H335-H361-H361?
• Safety Statements: P203-P210-P220-P240-P241-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable solids	Flam. Sol.	1	H228
Oxidising solids	Ox. Sol.	2	H272
Reproductive toxicity	Repr.	2	H361f
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	2	H361
Oxidising liquids	Ox. Liq.	2	H272
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	5	H303
Flammable solids	Flam. Sol.	2	H228

Discovery and Applications

4-Methylmorpholine N-oxide is an important chemical compound with the molecular formula C₅H₁₁NO₂. It is a derivative of morpholine, a six-membered heterocyclic compound containing both nitrogen and oxygen atoms. 4-Methylmorpholine N-oxide has been widely studied and utilized due to its unique chemical properties and versatile applications.

The discovery of 4-methylmorpholine N-oxide can be traced back to the early 20th century when researchers were investigating the oxidation of morpholine derivatives. This compound is typically synthesized through the oxidation of 4-methylmorpholine using oxidizing agents such as hydrogen peroxide or peracids. The resulting product, 4-methylmorpholine N-oxide, is a white crystalline solid that is soluble in water and many organic solvents.

One of the most notable applications of 4-methylmorpholine N-oxide is in the field of organic synthesis as an oxidizing agent. It is commonly used in various oxidation reactions to convert alcohols into carbonyl compounds, such as aldehydes and ketones. This makes it a valuable reagent in both laboratory research and industrial processes. Its utility in these reactions is due to its ability to selectively oxidize substrates under mild conditions, which is advantageous in the synthesis of complex organic molecules.

In addition to its role as an oxidizing agent, 4-methylmorpholine N-oxide has significant applications in the textile and polymer industries. It is used as a catalyst in the polymerization of certain monomers, contributing to the production of high-performance polymers and fibers. Its catalytic properties enable the efficient formation of polymers with desired structural and functional properties, making it valuable for producing materials with specific characteristics.

The compound also finds applications in the field of environmental science. It is employed in processes for the treatment of industrial wastewater and the removal of pollutants. Its ability to facilitate oxidative reactions makes it useful in breaking down organic contaminants and improving the quality of effluents.

In the pharmaceutical industry, 4-methylmorpholine N-oxide is used in the synthesis of various drugs and pharmaceutical intermediates. Its role in the oxidation of organic compounds is essential for the production of active pharmaceutical ingredients and other medicinal products.

Overall, 4-methylmorpholine N-oxide is a versatile chemical with a wide range of applications across different industries. Its role as an oxidizing agent, catalyst, and environmental treatment agent underscores its significance in advancing chemical processes and technologies.

References

2009. Enhanced enzymatic hydrolysis of sugarcane bagasse by N-methylmorpholine-N-oxide pretreatment. Bioresource Technology, 100(2).
DOI: 10.1016/j.biortech.2008.07.001

2021. Optimization of biogas yield from lignocellulosic materials with different pretreatment methods: a review. Biotechnology for Biofuels and Bioproducts, 14(1).
DOI: 10.1186/s13068-021-02012-x

2012. Kinetic modeling of rapid enzymatic hydrolysis of crystalline cellulose after pretreatment by NMMO. Journal of Industrial Microbiology and Biotechnology, 39(3).
DOI: 10.1007/s10295-011-1048-y