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4-Methylmorpholine

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4-Methylmorpholine Basic information

Product Name:
4-Methylmorpholine
Synonyms:
  • NMM
  • N-Methyl morphofine
  • N-METHYLMORPHOLINE
  • 4-METHYL-1-OXA-4-AZACYCLOHEXANE
  • 4-METHYLMORPHOLINE
  • AKOS 89985
  • LUPRAGEN(R) N 105
  • 1-Methylmorpholine
CAS:
109-02-4
MF:
C5H11NO
MW:
101.15
EINECS:
203-640-0
Product Categories:
  • Building Blocks
  • Heterocyclic Building Blocks
  • Morpholines
  • Protein Sequencing
  • Protein Structural Analysis
  • Reagents for Protein Sequencing
  • MorpholinesEssential Chemicals
  • Reagent Plus
  • Routine Reagents
  • Building Blocks
  • Chemical Synthesis
  • proteins
  • Organic solvents
  • Indazoles
  • Heterocyclic Building Blocks
  • Morpholines/Thiomorpholines
Mol File:
109-02-4.mol
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4-Methylmorpholine Chemical Properties

Melting point:
−66 °C(lit.)
Boiling point:
115-116 °C750 mm Hg(lit.)
Density 
0.92 g/mL at 25 °C(lit.)
vapor density 
>1 (vs air)
vapor pressure 
18 mm Hg ( 20 °C)
refractive index 
n20/D 1.435(lit.)
Flash point:
75 °F
storage temp. 
Store below +30°C.
pka
7.38(at 25℃)
form 
Liquid
Specific Gravity
0.920 (20/4℃)
color 
Clear
PH
10.6 (50g/l, H2O, 20℃)
explosive limit
2.1%(V)
Water Solubility 
>500 g/L (20 ºC)
Merck 
14,6277
BRN 
102719
InChIKey
SJRJJKPEHAURKC-UHFFFAOYSA-N
CAS DataBase Reference
109-02-4(CAS DataBase Reference)
NIST Chemistry Reference
Morpholine, 4-methyl-(109-02-4)
EPA Substance Registry System
4-Methylmorpholine (109-02-4)
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Safety Information

Hazard Codes 
F,C
Risk Statements 
11-20/21/22-34-10-22
Safety Statements 
16-26-36/37/39-45-25
RIDADR 
UN 2535 3/PG 2
WGK Germany 
1
RTECS 
QE5775000
10-23
Autoignition Temperature
165 °C DIN 51794
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29349990
Toxicity
LD50 orally in Rabbit: 1960 mg/kg LD50 dermal Rabbit 1240 mg/kg

MSDS

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4-Methylmorpholine Usage And Synthesis

Chemical Properties

colorless and transparent liquid. with characteristic odor. soluble in organic solvents, miscible with water and ethanol.

Uses

4-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. 4-Methylmorpholine is widely used in the synthesis of pesticide compounds such as insecticide, fungicide, plant growth regulator, etc. It is also used in the synthesis of fine chemicals such as surfactant, lubricant coolant, metal antirust agent, fiber treatment agent, etc.

Uses

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

Preparation

4-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.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 4881, 1995 DOI: 10.1016/0040-4039(95)00875-D

General Description

A water-white liquid with an ammonia-like odor. Less dense than water and insoluble in water. Flash point 75°F. May be moderately toxic by ingestion, inhalation and skin absorption. Very irritating to skin, eyes, and mucous membranes. Used as a solvent and to make pharmaceuticals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

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

May cause toxic effects if inhaled or ingested/swallowed. 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.

Safety Profile

Moderately toxic by ingestion and skin contact. Mildly toxic by inhalation. 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

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). [Hall J Phys Chem 60 63 1956, Beilstein 27 I 203, 27 III/IV 22.]

4-Methylmorpholine Supplier

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