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.

solubility 

Chloroform (Soluble), Ethyl Acetate, Methanol (Slightly)

form 

Liquid

pka

7.38(at 25℃)

color 

Clear

Specific Gravity

0.920 (20/4℃)

PH

10.6 (50g/l, H2O, 20℃)

explosive limit

2.1%(V)

Water Solubility 

>500 g/L (20 ºC)

Merck 

14,6277

BRN 

102719

Stability:

Volatile

InChIKey

SJRJJKPEHAURKC-UHFFFAOYSA-N

LogP

-0.32 at 25℃

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)

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

F 

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

• Language:English Provider:4-Methyl-1-oxa-4-azacyclohexane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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.

Flammability and Explosibility

Flammable

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 (109-02-4)Related Product Information

• 1-Methylpyrrolidine
• 1-Methylimidazole
• Thiophanate-methyl
• Methyl salicylate
• Moroxydine
• Morpholine
• N-Methyl-2-pyrrolidone
• Pirimiphos-methyl
• N,N-Dimethylformamide
• Moroxydine hydrochloride
• Tridemorph
• Tribenuron methyl
• Kresoxim-methyl
• Dimethomorph
• N-Formylmorpholine
• Methyl acetate
• METSULFURON METHYL
• Sodium carboxymethyl cellulose