N-METHYLMORPHOLINE

N-Methylmorpholine is used as a base catalyst for generation of polyurethanes and other reactions.
N-Methylmorpholine is produced by the reaction of methylamine and diethylene glycol as well as by the hydrogenolysis of N-formylmorpholine.
N-Methylmorpholine is the precursor to N-methylmorpholine N-oxide, a commercially important oxidant.

CAS Number: 109-02-4
EC Number: 203-640-0
Chemical formula: C5H11NO
Molar mass: 101.149 g·mol−1

N-Methylmorpholine is the organic compound with the formula O(CH2CH2)2NCH3.
N-Methylmorpholine is a colorless liquid.
N-Methylmorpholine is a cyclic tertiary amine.

Physical Description of N-Methylmorpholine:
N-Methylmorpholine appears as a water-white liquid with an ammonia-like odor.
N-Methylmorpholine is less dense than water and insoluble in water.

N-Methylmorpholine may be moderately toxic by ingestion, inhalation and skin absorption.
N-Methylmorpholine is very irritating to skin, eyes, and mucous membranes.
N-Methylmorpholine is used as a solvent and to make pharmaceuticals.

Applications of N-Methylmorpholine:
N-Methylmorpholine is used as a solvent for dyes, resins, waxes and pharmaceuticals.
N-Methylmorpholine acts as a crosslinker in the preparation of polyurethane foams, elastomers and adhesives.

N-Methylmorpholine is used as a precursor to prepare N-methylmorpholine N-oxide and morpholinium cation based ionic liquids.
N-Methylmorpholine is utilized as corrosion inhibitors and anti-scaling agents in industries.

Properties of N-Methylmorpholine:
Chemical formula: C5H11NO
Molar mass: 101.149 g·mol−1
Appearance : Liquid
Density: 0.92 g/cm3
Melting point: −66 °C (−87 °F; 207 K)
Boiling point: 115 to 116 °C (239 to 241 °F; 388 to 389 K)
Acidity (pKa): 7.38 (for the conjugate acid) (H2O)

N-Methylmorpholine (NMM) is an aliphatic, tertiary amine.
N-Methylmorpholine is a morpholine-containing compound used for protein sequencing analysis.

Coatings:
N-Methylmorpholine is used as a neutralizing amine for water reducible alkyd coatings

Pharmaceuticals:
N-Methylmorpholine serves mainly as a reagent in the synthesis of active pharmaceutical ingredients.

Applications of N-Methylmorpholine:
N-Methylmorpholine can be used as:
-A precursor to prepare N-methylmorpholine N-oxide and 1-butyl-1-methylmorpholinium bromide ([BMmo][Br]), a monocation ionic liquid.
-A reactant to synthesize quaternary ammonium complexes applicable as complexing agents in redox flow batteries.
-A basic catalyst in the synthesis of thiobenzamides via Willgerodt-Kindler′s reaction.
-An activating agent to synthesize hyaluronic acid-based biopolymer for cosmetic, pharmaceutical, and nutraceutical applications.

Chemical Properties of N-Methylmorpholine:
N-Methylmorpholine is colorless and transparent liquid with characteristic odor.
N-Methylmorpholine is soluble in organic solvents, miscible with water and ethanol.

Uses of N-Methylmorpholine:
N-Methylmorpholine is an excellent solvent, emulsifier, corrosion inhibitor, Catalyst in polyurethane foamsextraction solvent, stabilizing agent for chlorinated hydrocarbons, and also can be used as pesticide intermediates.
N-Methylmorpholine is widely used in the synthesis of pesticide compounds such as insecticide, fungicide, plant growth regulator, etc.
N-Methylmorpholine is also used in the synthesis of fine chemicals such as surfactant, lubricant coolant, metal antirust agent, fiber treatment agent, etc.

Uses of N-Methylmorpholine:
N-Methylmorpholine is used as a solvent for dyes, resins, waxes and pharmaceuticals.
N-Methylmorpholine acts as a crosslinker in the preparation of polyurethane foams, elastomers and adhesives.
N-Methylmorpholine is used as a precursor to prepare N-methylmorpholine N-oxide and morpholinium cation based ionic liquids.
N-Methylmorpholine is utilized as corrosion inhibitors and anti-scaling agents in industries.

Preparation of N-Methylmorpholine:
N-Methylmorpholine preparation method is to slowly add formaldehyde in morpholine drop by drop, under stirring add formic acid reaction, automatic reflux, and release carbon dioxide.
After adding formic acid, heating reflux 4 ~ 5h, cooling and adding sodium hydroxide immediately distillation, collect all the fraction before the boiling point of 99 ℃, and then add sodium hydroxide in the fraction to saturation, cooling the oil layer, drying, fractional distillation, to obtain N-methylmorpholine.

General Description of N-Methylmorpholine:
N-Methylmorpholine is a water-white liquid with an ammonia-like odor.
N-Methylmorpholine is less dense than water and insoluble in water.
Flash point 75°F.

Air & Water Reactions of N-Methylmorpholine:
Highly flammable.
N-Methylmorpholine is insoluble in water.

Reactivity Profile of N-Methylmorpholine:
Amines are chemical bases.
They neutralize acids to form salts plus water.
These acid-base reactions are exothermic.

The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base.
Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard:
Flammable, dangerous fire risk.
Skin irri-tant.

Health Hazard:
N-Methylmorpholine may cause toxic effects if inhaled or ingested/swallowed.
N-Methylmorpholine contact with substance may cause severe burns to skin and eyes.

Fire will produce irritating, corrosive and/or toxic gases.
Vapors may cause dizziness or suffocation.
Runoff from fire control or dilution water may cause pollution.

Fire Hazard:
Flammable/combustible material.
May be ignited by heat, sparks or flames.
Vapors may form explosive mixtures with air.

Vapors may travel to source of ignition and flash back.
Most vapors are heavier than air.
They will spread along ground and collect in low or confined areas (sewers, basements, tanks).

Vapor explosion hazard indoors, outdoors or in sewers.
Runoff to sewer may create fire or explosion hazard.
Containers may explode when heated.
Many liquids are lighter than water.

Flammability and Explosibility:
Flammable

Safety Profile:
Moderately toxic by ingestion and skin contact.
Mildly toxic by inhalation.

N-Methylmorpholine is an irritant to skin, eyes, and mucous membranes.
Flammable when exposed to heat or flame, can react vigorously with oxidizing materials.
When heated to decomposition it emits toxic fumes of NOx.

Purification Methods of N-Methylmorpholine:
Dry it by refluxing with BaO or sodium, then fractionally distil it through a helices-packed column.
The picrate has m 227o, the thiocyanate salt has m 103o (from butanone).

Identifiers of N-Methylmorpholine:
CAS Number: 109-02-4
Abbreviations: NMM
ChEMBL: ChEMBL2448839
ChemSpider: 7684
ECHA InfoCard: 100.003.310
EC Number: 203-640-0
PubChem CID: 7972
UNII: 11P91ANU5X
UN number: 2535
CompTox Dashboard (EPA): DTXSID9029146

N-Methylmorpholine is used as a base catalyst for generation of polyurethanes and other reactions.

KEYWORDS:
109-02-4, 203-640-0, Morpholine 4-methyl-, 1-Methylmorpholine, NSC, 9382, DSSTox_CID_9146, CCRIS 6691, Morpholinomethyl-polystyrene, UNII-11P91ANU5X

Physical State : Liquid
pH : 10.6
Storage : Store N-Methylmorpholine at room temperature
Boiling Point : 115-116° C (lit.) at 750
Density : 0.92 g/mL at 25° C (lit.)

Alternate Names: 4-methylmorpholin
Application: N-Methylmorpholine is a morpholine-containing compound used for protein sequencing analysis
CAS Number: 109-02-4
Purity: ≥99%
Molecular Weight: 101.15
Molecular Formula: C5H11NO
Supplemental Information: N-Methylmorpholine is classified as a Dangerous Good for transport and may be subject to additional shipping charges.

About N-Methylmorpholine:
N-Methylmorpholine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
N-Methylmorpholine is used in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses of N-Methylmorpholine:
ECHA has no public registered data indicating whether or in which chemical products N-Methylmorpholine might be used.
ECHA has no public registered data on the routes by which N-Methylmorpholine is most likely to be released to the environment.

Article service life of N-Methylmorpholine:
Other release to the environment of N-Methylmorpholine is likely to occur from: indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
N-Methylmorpholine can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones).

Widespread uses by professional workers of N-Methylmorpholine:
ECHA has no public registered data indicating whether or in which chemical products N-Methylmorpholine might be used.
ECHA has no public registered data on the types of manufacture using N-Methylmorpholine.
Other release to the environment of N-Methylmorpholine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).

Formulation or re-packing of N-Methylmorpholine:
ECHA has no public registered data indicating whether or in which chemical products N-Methylmorpholine might be used.
Release to the environment of N-Methylmorpholine can occur from industrial use: formulation of mixtures and formulation in materials.

Uses at industrial sites of N-Methylmorpholine:
N-Methylmorpholine is used in the following products: leather treatment products.
N-Methylmorpholine is used for the manufacture of: textile, leather or fur.
Release to the environment of N-Methylmorpholine can occur from industrial use: in the production of articles, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.

Manufacture of N-Methylmorpholine:
Release to the environment of N-Methylmorpholine can occur from industrial use: manufacturing of the substance.

Molecular Weight: 101.15
XLogP3: -0.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 101.084063974
Monoisotopic Mass: 101.084063974
Topological Polar Surface Area: 12.5 Å²
Heavy Atom Count: 7
Formal Charge: 0
Complexity: 50
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count   : 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Physico-chemical Properties of N-Methylmorpholine:
Molecular Formula: C5H11NO
Molar Mass: 101.15
Density: 0.92g/mLat 25°C(lit.)
Melting Point: −66°C(lit.)
Boling Point : 115-116°C750mm Hg(lit.)
Flash Point: 75°F
Water Solubility: >500 g/L (20 ºC)
Vapor Presure: 18 mm Hg ( 20 °C)
Vapor Density: >1 (vs air)
Appearance: Liquid
Specific Gravity: 0.920 (20/4℃)
Color: Clear
Merck: 14,6277
BRN: 102719
pKa: 7.38(at 25℃)
PH: 10.6 (50g/l, H2O, 20℃)
Storage Condition: Store N-Methylmorpholine below +30°C.
Explosive Limit: 2.1%(V)
Refractive Index: n20/D 1.435(lit.)

Physical and Chemical Properties of N-Methylmorpholine:
N-Methylmorpholine is a liquid with corrosive properties, slight toxicity and pungent odor, colorless transparent liquid.
viscosity (23 ℃): 2.3mPa · s
boiling range: 111~117 ℃
freezing point: -65 ~-66 ℃
refractive index (20 ℃): 1.4328~1.4337
vapor pressure (20 ℃): 2200Pa
solubility in water, pKa: = 7.5.
Explosion limit of: 2.2% ~ 11.8% in air, soluble in organic solvents, miscible with water and ethanol

Uses of N-Methylmorpholine:
N-Methylmorpholine is soluble in water, alcohol, ether, can be used as a solvent for rayon, corrosion inhibitors, but also for the synthesis of rubber accelerators and other fine chemicals, also used as a polyurethane catalyst, catalysts for the synthesis of aminobenzylpenicillin and hydroxypenicillin.
N-Methylmorpholine can be produced by double oxidation.

IUPAC name:
4-Methylmorpholine

Synonyms:
4-Methylmorpholine
N-METHYLMORPHOLINE
109-02-4
Morpholine, 4-methyl-
Methylmorpholine
1-Methylmorpholine
4-methylmorpholin
Morpholine, N-methyl-
N-methyl morpholine
4-Methylmorfolin
NSC 9382
4-methyl-morpholine
11P91ANU5X
NMM
NSC-9382
DSSTox_CID_9146
DSSTox_RID_78682
DSSTox_GSID_29146
4-Methylmorfolin [Czech]
N-Methylmorpholin
N-methyl morpholine hydrochloride
CAS-109-02-4
CCRIS 6691
EINECS 203-640-0
UN2535
Morpholinomethyl-polystyrene
UNII-11P91ANU5X
AI3-24289
4methylmorpholine
methyl-morpholine
N-methylmopholine
N-methylmorphline
N-methymorpholine
N-metylmorpholine
4-methlmorpholine
4-methylmopholine
4-methymorpholine
N-methyhnorpholine
N-methyimorpholine
Texacat NMM
4-methyimorpholine
4-Methyl-1-oxa-4-azacyclohexane
N-methyl morpholin
N-methyl-mopholine
N-methyl-morpholin
N-metyl-morpholine
4-methyl morpholin
N -methylmorpholine
N- methylmorpholine
N--methylmorpholine
N-mehtyl morpholine
N-methylmor-pholine
N-methylmorpho-line
p-Methyl morpholine
4 -methylmorpholine
4-methyl morpholine
MFCD00006175
4-N-methylmorpholine
N- methyl morpholine
N-methyl -morpholine
4-(methyl)morpholine
morpholine, 4-methyl
morphlinomethyl-polystyrene
Methylmorpholine (Related)
morpholinomethyl polystyrene
EC 203-640-0
SCHEMBL4622
WLN: T6N DOTJ A1
4-Methylmorpholine, redistilled
N-METHYLMORPHOLINE [MI]
CHEMBL2448839
DTXSID9029146
NSC9382
BCP31356
STR02354
Tox21_202412
Tox21_303402
STL294217
ZINC19230118
AKOS000118797
UN 2535
4-Methylmorpholine or n-methylmorpholine
NCGC00249222-01
NCGC00257448-01
NCGC00259961-01
BP-20398
4-Methylmorpholine, ReagentPlus(R), 99%
DB-059805
FT-0648820
FT-0658371
FT-0701320
M0370
4-Methylmorpholine, purum, >=98.0% (GC)
EN300-18961
N-Methyl morphofine pound>>Morpholine, 4-methyl-
N-Methylmorpholine, SAJ special grade, >=99.0%
J-002223
J-515790
Q2542075
F0001-0190
109-02-4 [RN]
11P91ANU5X
203-640-0 [EINECS]
4-Methylmorfolin [Czech]
4-Methylmorpholin [German] [ACD/IUPAC Name]
4-Methylmorpholine [ACD/IUPAC Name]
4-Méthylmorpholine [French] [ACD/IUPAC Name]
MFCD00006175 [MDL number]
Morpholine, 4-methyl- [ACD/Index Name]
Morpholine, N-methyl-
N-Methylmorpholine [Wiki]
NMM
QE5775000
[109-02-4] [RN]
138048-80-3 [RN]
1-Methylmorpholine
203-640-0MFCD00006175
211-678-4 [EINECS]
4/2/109
4-Methyl-1-oxa-4-azacyclohexane
4-Methylmorfolin
4-Methylmorfolin [Czech]
4-Methylmorpholine N-oxide
4-Methylmorpholine, redistilled
EINECS 203-640-0
MES
Methylmorpholine
morpholine, 4-methyl
N-methyl morpholine
N-Methyl-morpholine
N-Methylmorpholine (en)
NMM, N-Methylmorpholine
p-Methyl morpholine
STR02354
T6N DOTJ A1 [WLN]
Texacat NMM [Trade name]
UN 2535
UNII:11P91ANU5X
UNII-11P91ANU5X
WLN: T6N DOTJ A1
4-Methylmorpholine, purified by redistillation, >=99.5%
4-Methylmorpholine or n-methylmorpholine [UN2535] [Flammable liquid]
Morpholinomethyl-polystyrene, extent of labeling: ~3.5 mmol/g base loading
4-Methylmorpholine, BioXtra, suitable for protein sequencing, >=99.5% (GC)

Regulatory process names:
4-methylmorpholine
4-methylmorpholine
4-METHYLMORPHOLINE (N-METHYLMORPHOLINE)
Morpholine, 4-methyl-

CAS names:
Morpholine, 4-methyl-

IUPAC names:
1-Methylmorpholine
4-Methylmorpholin
4-Methylmorpholine
4-methylmorpholine
4-methylmorpholine
4-methylmorpholineN-methylmorpholine
n-Methyl morpholine
N-Methylmorpholine

Trade names:
N-Methylmorpholine
NMM

Other identifiers:
109-02-4
205657-43-8
205657-43-8