Methyl morpholine oxide
NMO · 4-METHYLMORPHOLINE 4-OXIDE · N-Methylmorpholine oxide · Morpholine, 4-methyl-, 4-oxide · 4-methyl-morpholin4-oxide · MMNO · 4-methyl-4-oxidomorpholin-4-ium · 4-methylmorpholine n-oxide solution
Identifiers & Physical Properties
| CAS No. | 7529-22-8 |
|---|---|
| Molecular formula | C5H11NO2 |
| Average molar mass | 117.15 g/mol |
| Monoisotopic mass | 117.07897859 g/mol |
| SMILES | C[N+]1([O-])CCOCC1 |
| InChIKey | LFTLOKWAGJYHHR-UHFFFAOYSA-N |
| PubChem CID | 82029 |
| ChEMBL | CHEMBL3184330 |
| ChEBI | CHEBI:52093 |
| EC No. | 231-391-8 |
| DTXSID | DTXSID3029287 |
Chemical & Physical Properties
| XLogP | -0.7 |
|---|---|
| Topological polar surface area | 27.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 78.5 |
| Chemical classes | Nitrogen Compounds -> Amine Oxides |
| Cosmetics | CleansingFoam boostingSurfactant |
| Physical Description | LiquidWhite hygroscopic solid[Merck Index] Light yellow crystalline solid[Sigma-Aldrich MSDS] |
| Melting point | 180-184 °C(lit.) |
| Boiling point | 118-119°C |
| Density | 1,14 g/cm3 |
| Vapor pressure | 1.41hPa at 20℃ |
| Refractive index | n20/D 1.43 |
| Flash point | 118-119°C |
| Storage conditions | 2-8°C |
| Solubility | DMSO (Soluble), Methanol (Slightly)Soluble in water, methanol, ethanol, acetone, ethers and dimethylsulfoxide. |
| Physical state | Liquid |
| pKa (acidity coefficient) | 4.93±0.20(Predicted) |
| Color | Clear colorless to yellow |
| pH | 9.00 ( in neat) |
| BRN | 507437 |
| Stability | Hygroscopic |
| Cosmetics Ingredients Functions | SURFACTANT - FOAM BOOSTINGSURFACTANT - CLEANSINGCLEANSING |
| InChI | 1S/C5H11NO2/c1-6(7)2-4-8-5-3-6/h2-5H2,1H3 |
| InChIKey | LFTLOKWAGJYHHR-UHFFFAOYSA-N |
| SMILES | C[N+]1([O-])CCOCC1 |
| LogP (partition coefficient) | -1.2 at 25℃ |
| CAS DataBase Reference | 7529-22-8(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | ARC64PKJ0F |
| NIST Chemistry Reference | N-Methylmorpholine-N-oxide(7529-22-8) |
| EPA Substance Registry System | Morpholine, 4-methyl-, 4-oxide (7529-22-8) |
| UNSPSC Code | 12352119 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS03,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H228-H272-H361f |
| GHS precautionary statements | P202-P210-P220-P240-P241-P308+P313 |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36/37 |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| Customs code | 29349990 |
| Storage class | 4.1B - Flammable solid hazardous materials |
| Hazard class | Flam. Sol. 1Repr. 2 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.5% (1 of 202) of reports.DangerH228 (66.8%): Flammable solid [Danger Flammable solids]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, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 202 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Morpholine, 4-methyl-, 4-oxideMorpholine, 4-methyl-, 4-oxide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Morpholine, 4-methyl-, 4-oxide are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 12-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15946Morpholine, 4-methyl-, 4-oxide: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | An irritant[Merck Index] An oxidizer that may intensify fire[ECHA REACH Registrations] A skin and strong eye irritantMay cause allergic reactions in sensitive individuals, based on QSAR modeling[Sigma-Aldrich MSDS] Search for (7529-22-8[EC/RN Number]) AND (allergic OR sensitizer OR sensitization OR dermatitis): no results[PubMed] |
| Hazard Classes and Categories | Flam. Sol. 1 (66.8%) |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| Customs code | 29349990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS03,GHS08 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36/37 |
| Storage class | 4.1B - Flammable solid hazardous materials |
| GHS hazard statements | H228-H272-H361f |
| REACH registrations | Active |
| Hazard class | Flam. Sol. 1Repr. 2 |
| GHS precautionary statements | P202-P210-P220-P240-P241-P308+P313 |
Applications & Uses
Uses
4-Methylmorpholine N-Oxide is a metabolite of Morpholine (M723725). N-Methylmorpholine N-Oxide is commonly used to dissolve cellulose as well as in the dissolution of of scleroproteins.
Uses
4-Methylmorpholine N-oxide acts as a non-metallic catalyst for the cyanosilylation of ketones. It is also employed as a co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids. It serves as a solvent in the Lyocell process to produce tencel fiber. Further, it is used in the preparation of aldehydes from primary alcohols in the presence of tetrapropylammonium perruthenate.
Uses
Non-metallic catalyst for the cyanosilylation of ketones. Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.
General Description
4-MethylmorpholineN-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis. In recent studies, it has been used as a catalyst in silylcyanation of aldehydes and ketones. Lyocell, a regenerated cellulose fiber, can be prepared using 4-methylmorpholineN-oxide in an eco-friendly manner.