141-91-3

Basic information

• Product Name: Dimethylmorpholine
• Synonyms: 2,6-Dimethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine;2,6-Dimethylmorfolin;2,6-dimethyl-morpholin;2,6-Dimethylmorpholine,c&t;AKOS BBS-00004469;2，6-Dimethyl-2，3，5，6-thtrahydro-4H-oxazine;2，6-Dimethyl morphaline;2,6-DIMETHYLMORPHOLINE
• CAS NO: 141-91-3
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• EINECS: 205-509-3
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Morpholines;Building Blocks;C4 to C10;Chemical Synthesis;Heterocyclic Building Blocks;Morpholines/Thiomorpholines
• Mol File: 141-91-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: −85 °C(lit.)
• Boiling Point: 147 °C(lit.)
• Flash Point: 120 °F
• Appearance: colourless liquid
• Density: 0.935 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.128mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• PKA: 9.04±0.60(Predicted)
• Water Solubility: >=0.01 g/100 mL at 19 ºC
• Stability: Stable. Incompatible with oxidizing agents, strong acids. Flammable.
• BRN: 103036
• CAS DataBase Reference: Dimethylmorpholine(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethylmorpholine(141-91-3)
• EPA Substance Registry System: Dimethylmorpholine(141-91-3)

Safety Data

• Hazard Codes: Xn
• Statements: 10-21-41
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 1992 3/PG 3
• WGK Germany: 2
• RTECS: QE1750000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 141-91-3(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

cis-2,6-Dimethylmorpholine (DMMP) has been used in the preparation of microporous material composed of hybrid T2 and T3 supertetrahedral clusters.

General Description

Clear liquid.

Air & Water Reactions

Highly flammable. Very slightly water soluble.

Reactivity Profile

Dimethylmorpholine reacts with oxidizing agents . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

Dimethylmorpholine is combustible.

Flammability and Explosibility

Flammable

InChI:InChI=1/C6H13NO/c1-6(2)5-7-3-4-8-6/h7H,3-5H2,1-2H3

Synthetic route

2,2'-oxydipropanol (108-61-2) → 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
With ammonia; hydrogen at 200℃; under 150015 Torr; Reagent/catalyst; Temperature;	95%

bis(1-chloro-2-propyl) ether (108-60-1) → 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
With ammonium hydroxide at 120℃;
With ammonium hydroxide at 120℃;

toluene-4-sulfonamide (70-55-3) + 1-Chloro-2-propanol (127-00-4) → 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
With sodium hydroxide Erhitzen des Reaktionsprodukts mit H2SO4 auf 180grad;

diisopropanolamine (110-97-4) → 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
With sulfuric acid at 170℃;

diallylamine (124-02-7) → 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
Reaktion ueber mehrere Stufen;

sulfuric acid (7664-93-9) + diisopropanolamine (110-97-4) → 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
at 160 - 170℃;

2,6-dimethyl-N-(2-hydroxypropyl)-morpholine (63295-51-2) → 2,6-dimethyl morpholine (141-91-3) + N-(2-propenyl-2,6-dimethylmorpholine

Conditions	Yield
With nitrogen In water; SiO2

2,6-dimethyl-N-(2-hydroxypropyl)-morpholine (63295-51-2) + Al2 O3 → 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
In water

2,2'-oxydipropanol (108-61-2) → 2,6-dimethyl morpholine (141-91-3) + C6H15NO2

Conditions	Yield
With ammonia; hydrogen at 180℃; under 150015 Torr; Temperature; Overall yield = 66.3 %;

morpholine (110-91-8) + methanol (67-56-1) → 4-methyl-morpholine (109-02-4) + 2,6-dimethyl morpholine (141-91-3)

Conditions	Yield
With Iridium(II)-coordinated mesoporous (4-[5-(4-aminophenyl)-4'-methyl-[1,1'-biphenyl]-3-yl]aniline)-modified Tröger’s base-functionalized polymer at 110℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature;	A 89 %Chromat. B n/a

2,6-dimethyl morpholine (141-91-3) + trimethylsilyl isocyanate (1118-02-1) → 2,6-dimethyl-morpholine-4-carboxylic acid amide (139994-85-7)

Conditions	Yield
In isopropyl alcohol at 20℃;	100%

2,6-dimethyl morpholine (141-91-3) + benzyl 3-nitro-1H-1,2,4-triazole-1-carboxylate (1001067-06-6) → benzyl 2,6-dimethylmorpholine-4-carboxylate (1001067-13-5)

Conditions	Yield
In dichloromethane at 20℃; for 0.0833333h;	100%

2,6-dimethyl morpholine (141-91-3) + 9-fluorenylmethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate (1001067-08-8) → (9H-fluoren-9-yl)methyl 2,6-dimethylmorpholine-4-carboxylate (1001067-15-7)

Conditions	Yield
In dichloromethane at 20℃; for 0.0833333h;	100%

2,6-dimethyl morpholine (141-91-3) + 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate (1001067-09-9) → 2-(trimethylsilyl)ethyl 2,6-dimethylmorpholine-4-carboxylate (1001067-16-8)

Conditions	Yield
In dichloromethane at 20℃; for 0.0833333h;	100%

2,6-dimethyl morpholine (141-91-3) + 4-(3-bromopropoxy)-3-methoxybenzaldehyde (148433-00-5) → C17H25NO4

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	100%
With potassium carbonate In acetonitrile Reflux;

2,6-dimethyl morpholine (141-91-3) + Ethylchlor<4-(3-chlorphenyl)-piperazin-1-ylamido>phosphat (98183-26-7) → Ethyl<4-(3-chlorphenyl)-piperazin-1-ylamido>-(2,6-dimethylmorpholin-4-ylamido)phosphat

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	99%

2,6-dimethyl morpholine (141-91-3) + Ethylchlor<4-(2-chlorphenyl)-piperazin-1-ylamido>phosphat (98156-28-6) → Ethyl<4-(2-chlorphenyl)-piperazin-1-ylamido>-(2,6-dimethylmorpholin-4-ylamido)phosphat

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	99%

2,6-dimethyl morpholine (141-91-3) + Ethylchlor<4-(3-trifluormethylphenyl)-piperazin-1-ylamido>phosphat (98156-50-4) → Ethyl<4-(3-trifluormethylphenyl)-piperazin-1-ylamido>-(2,6-dimethylmorpholin-4-ylamido)phosphat

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	99%

2,6-dimethyl morpholine (141-91-3) + (4-chlorophenyl)(3-chloropropyl)methylpropylsilane (191926-73-5) → 4-{3-[(4-Chloro-phenyl)-methyl-propyl-silanyl]-propyl}-2,6-dimethyl-morpholine

Conditions	Yield
With sodium iodide 90-100 deg C, 2 h, then toluene, reflux, 48 h;	99%

2,6-dimethyl morpholine (141-91-3) + formaldehyd (50-00-0) + C11H12N4O2 → 1-(2,6-dimethylmorpholino-4-yl-methyl)-3-ethyl-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one

Conditions	Yield
In ethanol for 3h; Reflux;	99%

2,6-dimethyl morpholine (141-91-3) + (benzyloxy)benzene (946-80-5) → 4-cyclohexyl-2,6-dimethylmorpholine (1774-04-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In m-xylene at 90℃; under 7500.75 Torr; for 6h; Autoclave; Green chemistry;	99%

2,6-dimethyl morpholine (141-91-3) + Ethylchlor<<2-(2,6-dichlorphenoxy)-ethyl>-propylamido>phosphat (98156-25-3) → Ethyl<<2-(2,6-dichlorphenoxy)-ethyl>-propylamido>(2,6-dimethyl-morpholin-4-ylamido)phosphat

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	98%

2,6-dimethyl morpholine (141-91-3) + isatoic anhydride (118-48-9) → (2-aminophenyl)(2,6-dimethylmorpholino)methanone

Conditions	Yield
With dmap In N,N-dimethyl-formamide 1) 0 deg C, 2-3 h, 2) room temperature, 20-24 h;	98%
With dmap In acetonitrile at 0 - 20℃; for 26h; Schlenk technique; Inert atmosphere;

2,6-dimethyl morpholine (141-91-3) + 1-Bromo-3-phenylpropane (637-59-2) → 1-N-(2',6'-dimethyl-morpholino)-3-phenyl-propane (415957-91-4)

Conditions	Yield
Heating;	98%

2,6-dimethyl morpholine (141-91-3) + 4-Fluoronitrobenzene (350-46-9) → 2,6-dimethyl-4-(4-nitrophenyl)morpholine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃;	98%

2,6-dimethyl morpholine (141-91-3) + methyl 4-((((4-nitrophenoxy)carbonyl)(6-(trifluoromethyl)pyridin-2-yl)amino)methyl)benzoate → methyl 4-((2,6-dimethyl-N-(6-(trifluoromethyl)pyridin-2-yl)morpholine-4-carboxamido)methyl)benzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 0.5h; Microwave irradiation;	97.7%

2,6-dimethyl morpholine (141-91-3) + cyclododecanone (830-13-7) → dodemorph (1593-77-7, 91269-47-5, 91269-48-6)

Conditions	Yield
With hydrogen; ZrO2-containing catalyst at 220 - 240℃; under 37503.8 Torr;	97%

2,6-dimethyl morpholine (141-91-3) + 7-chloro-1-(2,4-difluorophenyl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinolone-3-carboxylic acid (1146300-32-4) → 1-(2,4-difluorophenyl)-1,4-dihydro-7-(2,6-dimethylmorpholin-4-yl)-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid (1146300-57-3)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide Microwave irradiation;	97%

2,6-dimethyl morpholine (141-91-3) + (4-chlorobutyl)(4-chlorophenyl)(3-chloropropyl)methylsilane (191926-75-7) → (4-chlorophenyl)[4-(2,6-dimethylmorpholin-4-yl)butyl][3-(2,6-dimethylmorpholin-4-yl)propyl]methylsilane

Conditions	Yield
With sodium iodide 90-100 deg C, 2xh, then toluene, reflux, 48 h;	96%

2,6-dimethyl morpholine (141-91-3) + Bis-(4-chloro-phenyl)-(3-chloro-propyl)-methyl-silane (191926-72-4) → 4-{3-[Bis-(4-chloro-phenyl)-methyl-silanyl]-propyl}-2,6-dimethyl-morpholine

Conditions	Yield
With sodium iodide 90-100 deg C, 2 h, then reflux, 48 h;	96%

2,6-dimethyl morpholine (141-91-3) + Ethylchlor<<2-(2,4,6-trichlorphenoxy)-ethyl>-propylamido>phosphat (98156-27-5) → Ethyl<<2-(2,4,6-trichlorphenoxy)-ethyl>-propylamido>(2,6-dimethyl-morpholin-4-ylamido)phosphat

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	95%

2,6-dimethyl morpholine (141-91-3) → 2,3,3,4,5,5,6-Heptafluoro-2,6-bis-trifluoromethyl-morpholine (131968-14-4)

Conditions	Yield
With fluorine at -100 - 25℃;	95%

2,6-dimethyl morpholine (141-91-3) + 4-methyl-N-2-propen-1-yl-N-[2-[tris(1-methylethyl)silyl]ethynyl]-benzenesulfonamide (945536-26-5) → C24H42N2O3SSi

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran at 80℃; Inert atmosphere;	95%

2,6-dimethyl morpholine (141-91-3) + 2,2,2-trichloroethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate (1001067-07-7) → 2,2,2-trichloroethyl 2,6-dimethylmorpholine-4-carboxylate (1001067-14-6)

Conditions	Yield
In dichloromethane at 20℃; for 0.0833333h;	94%

2,6-dimethyl morpholine (141-91-3) + ethyl 4,5-dimethyl-2-(1H-tetrazol-1-yl)thiophene-3-carboxylate (332163-80-1) → 2-(2,6-dimethylmorpholin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one

Conditions	Yield
In neat (no solvent) at 80 - 90℃; for 0.5h;	94%

2,6-dimethyl morpholine (141-91-3) + 2-trifluoromethylphenyl-4-chlorobutylvinylmethylsilane → 2-trifluoromethylphenyl-4-(2,6-dimethylmorpholino)butylvinylmethylsilane

Conditions	Yield
With potassium iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; ethyl acetate	93%

2,6-dimethyl morpholine (141-91-3) + 3-chloro-1,2-dimethyl-5-phenylpyrazolium iodide (59803-61-1) → 5-(2,6-Dimethyl-morpholin-4-yl)-1,2-dimethyl-3-phenyl-2H-pyrazol-1-ium; iodide

Conditions	Yield
In ethanol Heating;	92%

2,6-dimethyl morpholine (141-91-3) + (4-chlorophenyl)(3-chloropropyl)methyl(prop-2-en-1-yl)silane (191926-74-6) → 4-{3-[Allyl-(4-chloro-phenyl)-methyl-silanyl]-propyl}-2,6-dimethyl-morpholine

Conditions	Yield
With sodium iodide 90-100 deg C, 2 h, then toluene, reflux, 48 h;	92%

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 127-00-4 1-Chloro-2-propanol 
• 7664-93-9 sulfuric acid 
• 110-97-4 diisopropanolamine 
• 63295-51-2 2,6-dimethyl-N-(2-hydroxypropyl)-morpholine 
• 108-61-2 2,2'-oxydipropanol 
• 110-91-8 morpholine 
• 67-56-1 methanol 
• 124-02-7 diallylamine 
• 108-60-1 bis(1-chloro-2-propyl) ether 

Downstream Products

• 107779-03-3 2-(2,6-dimethyl-morpholino)-1-phenyl-ethanol 
• 102-78-3 2-(2,6-dimethyl-morpholin-4-ylsulfanyl)-benzothiazole 
• 102165-78-6 4-[2-(2,6-dimethyl-morpholino)-acetylamino]-benzoic acid isobutyl ester 
• 61636-30-4 4-benzyl-2,6-dimethylmorpholine 
• 90950-33-7 4-<2,3-Epoxy-propyl>-2,6-dimethyl-morpholin 
• 64568-28-1 2,6-dimethyl-4-(4-nitro-thiobenzoyl)-morpholine 
• 76492-90-5 fenpropimorph 
• 84145-73-3 3-(2,6-Dimethyl-morpholin-4-yl)-propionitrile 
• 131968-14-4 2,3,3,4,5,5,6-Heptafluoro-2,6-bis-trifluoromethyl-morpholine 
• 66840-50-4 1-ethoxy-perfluoropropane 
• 83935-39-1 bis(perfluoroisopropyl) ether 

Relevant articles and documents

Preparation method of high-purity cis-2,6-dimethylmorpholine

The invention relates to the technical field of chemical synthesis of medicines, and discloses a preparation method of high-purity cis-2,6-dimethylmorpholine. The method comprises the following steps:subjecting a cis-2,6-dimethylmorpholine-rich mixture of cis-2,6-dimethylmorpholine, trans-2, 6-dimethylmorpholine, cis-2,5-dimethylmorpholine and trans-2,5-dimethylmorpholine to salt formation with micromolecular aliphatic carboxylic acid in an ester solvent, and carrying out recrystallizing to obtain cis-2,6-dimethylmorpholine carboxylate; and dissociating the cis-2,6-dimethylmorpholine carboxylate by using a strong alkaline substance to obtain the high-purity cis-2,6-dimethylmorpholine. According to the method disclosed by the invention, environment-friendly ethyl acetate, isopropyl acetateand butyl acetate are used as reaction solvents and also used as recrystallization solvents, so realization of green production is facilitated which reduction of pollution is realized, impurity content is effectively controlled, finished product purity reaches 99.9% or above, used acids and solvents are friendly to environment, and the method is suitable for industrial production.

Ionic liquid/H2O-mediated synthesis of mesoporous organic polymers and their application in methylation of amines

Mesoporous Tr?ger's base-functionalized polymers (Meso-TBPs) were prepared using a sulfonic acid group functionalized ionic liquid/H2O system, with surface areas up to 431 m2 g-1 and pore sizes of 3-15 nm. Ir(ii) coordinated Meso-TBPs exhibited extraordinary catalytic performance in the N-methylation of amines using methanol.

A concise and efficient synthesis of substituted morpholines

A simple and efficient method has been developed for the synthesis of substituted morpholines by a sequence of coupling, cyclization, and reduction reactions of easily available amino alcohols and α-halo acid chlorides. Various mono-, di-, and trisubstituted morpholines, spiro morpholines, and ring-fused morpholines, as well as morpholine homologues, were synthesized in good to excellent yields by a single methodology under similar reaction conditions. The method was also used in a multigram synthesis of (3S)-3-methylmorpholine.