Methyl morpholine oxide

HCID 82029CAS 7529-22-8
Substructure searchFind similar structures

Basic information

Standard SMILES
C[N+]1([O-])CCOCC1
InChIKey
LFTLOKWAGJYHHR-UHFFFAOYSA-N
Molecular formula
C5H11NO2
Average molar mass
117.15 g/mol
Monoisotopic mass
117.07897859

Overview

N-methylmorpholine N-oxide is a morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine.

Names & identifiers

Preferred name
Methyl morpholine oxide
IUPAC
4-methyl-4-oxidomorpholin-4-ium
English name
4-Methylmorpholine N-oxide
Molecular formula
C5H11NO2
Molecular weight
117.15

Names & synonyms

7529-22-84-Methylmorpholine 4-oxideN-Methylmorpholine oxideN-Methylmorpholine N-oxideMorpholine, 4-methyl-, 4-oxideMethyl morpholine oxide4-Methylmorpholine-4-oxide4-Methylmorpholine Oxide4-methylmorpholine-N-oxideN-Methylmorpholine 4-oxideNSC 73198NSC 82153
Show more names
NMO4-methyl-morpholin4-oxideMMNO4-methyl-4-oxidomorpholin-4-ium4-methylmorpholine n-oxide solution4-MethylMorpholin-4-iuM-4-olate
DTXSID3029287EINECS 231-391-8NSC-73198NSC-821534-methylmorpholine 4-oxide, monohydrateDTXCID509287CHEBI:52093EC 231-391-8

Database identifiers

CAS
7529-22-8
PubChem CID
82029
DTXSID
DTXSID3029287
ChEMBL
CHEMBL3184330
ChEBI
CHEBI:52093
UNII
ARC64PKJ0F
EC Number
231-391-8
Nikkaji
J256.599D

Properties

Computed structural properties

XLogP
-0.7
Topological polar surface area
27.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amine Oxides
CosmeticsCleansing; Foam boosting; Surfactant
Physical Description · 2 items

Liquid

White hygroscopic solid; [Merck Index] Light yellow crystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
180 · 180-184 °C(lit.)
Boiling point
118 · 118-119°C
Density
1 · 1,14 g/cm3
vapor pressure
1.41 hPa · 1.41hPa at 20℃
refractive index
20 · n20/D 1.43
Flash point
118 · 118-119°C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.5% (1 of 202) of reports.

Danger

H228 (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.

Hazard information

Regulatory Information · 4 items

Chemical: Morpholine, 4-methyl-, 4-oxide

Morpholine, 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/15946

Morpholine, 4-methyl-, 4-oxide: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

An irritant; [Merck Index] An oxidizer that may intensify fire; [ECHA REACH Registrations] A skin and strong eye irritant; May 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 CategoriesFlam. Sol. 1 (66.8%)

Safety data

wgk
1
tsca
TSCA listed
hs_code
29349990
risk_code
36/37/38
Signal word
Danger
Symbol(GHS)
GHS02,GHS03,GHS08

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as a reagent in synthetic organic chemistry and commercially for swelling and dissolution of cellulose; [Merck Index] Used as an intermediate, to make flexible and rigid polyurethane foams, as a solvent in synthetic fiber production, and in industrial and professional coatings, adhesives, and sealants; [ECHA REACH Registrations]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

U.S. Production2023: 500,000 - <1,000,000 lb
Industry UsesOther
Use ClassificationCosmetics -> Cleansing; Foam boosting; Surfactant
General Manufacturing Information · 2 items

Organic Fiber Manufacturing

Morpholine, 4-methyl-, 4-oxide: ACTIVE

Applications · 4 items

Uses4-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.

Uses4-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.

UsesNon-metallic catalyst for the cyanosilylation of ketones. Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.

General Description4-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.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南氟泽新材料有限公司00-15169181 15169181281 · [email protected]

Additional notes

DefinitionChEBI: N-methylmorpholine N-oxide is a morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine.

Related reactions

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Linked notes

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