N,N'-Dimorpholinomethane supplier

Name
N,N'-Dimorpholinomethane
EINECS 227-062-3
CAS No. 5625-90-1
Article Data44
CAS DataBase
Density 1.09 g/cm³
Solubility Soluble in water.
Melting Point
Formula C₉H₁₈N₂O₂
Boiling Point 265.1 °C at 760 mmHg
Molecular Weight 186.254
Flash Point 77.6 °C
Transport Information
Appearance Colorless Liquid
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi,F
Synonyms Morpholine,4,4'-methylenedi- (6CI,7CI,8CI);4,4'-Methylenebis[morpholine];4,4'-Methylenedimorpholine;Bis(morpholino)methane;Dimorpholinomethane;Methylenebismorpholine;N,N'-Methylenebismorpholine;
PSA 24.94000
LogP -0.51590

Synthetic route

: 110-91-8
morpholine

: 50-00-0
formaldehyd

: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
at 100℃; for 0.166667h; Microwave irradiation; Neat (no solvent);	98%
at 0 - 20℃; for 2.5h;	92%
In 1,4-dioxane at 20 - 70℃;	89.6%

: 52853-19-7
N-(methylene)morpholinium chloride

: 41316-44-3
3-methyl-3-ethyloxaziridine

A: 5625-90-1
4-(morpholinomethyl)morpholine

B: 5824-79-3
methylene-morpholin-4-yl-amine

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane for 5h;	A 0.7 g B 93%

...Expand

: 110-91-8
morpholine

: 51-80-9
bis-(dimethylamino)methane

: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
With samarium(III) nitrate hexahydrate at 60℃; for 10h; Reagent/catalyst; Temperature; Time;	90%
With samarium nitrate hexahydrate at 80℃; for 6h; Under argon;	89%

: 110-91-8
morpholine

: 50-00-0
formaldehyd

: 39648-74-3, 65355-00-2, 65355-14-8
(S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol

A: 5625-90-1
4-(morpholinomethyl)morpholine

: 758698-16-7
(S)-3,3'-bis(morpholinomethyl)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

Conditions

Conditions	Yield
Stage #1: morpholine; formaldehyd at 60℃; for 13h; Cooling with ice; Stage #2: (S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol In 1,4-dioxane at 60℃; for 18h; Inert atmosphere;	A n/a B 90%

...Expand

: 110-91-8
morpholine

: 39082-53-6
1,1-bis(phenylsulfonyl)ethylene

A: 5625-90-1
4-(morpholinomethyl)morpholine

B: 3406-02-8
bis(phenylsulfonyl)methane

C: 3561-68-0
1,1,3,3,-tetrakis(phenylsulfonyl)propane

D: 85523-51-9
4-(2,2-Bis-benzenesulfonyl-ethyl)-morpholine

Conditions

Conditions	Yield
In benzene at 80℃; for 2h; Product distribution;	A n/a B n/a C 81% D 5%

...Expand

: 13368-42-8
4-(trimethylsilyl)morpholine

: 85413-82-7
trimethyl(morpholinomethoxy)silane

A: 5625-90-1
4-(morpholinomethyl)morpholine

B: 107-46-0
Hexamethyldisiloxane

Conditions

Conditions	Yield
at 30℃; for 1h;	A 70% B 70%

...Expand

: 13368-42-8
4-(trimethylsilyl)morpholine

: 50-00-0
formaldehyd

A: 5625-90-1
4-(morpholinomethyl)morpholine

B: 107-46-0
Hexamethyldisiloxane

C: 85413-82-7
trimethyl(morpholinomethoxy)silane

Conditions

Conditions	Yield
at 25 - 30℃; for 1h;	A 40% B 40% C 60%

...Expand

: 110-91-8
morpholine

: 75-09-2
dichloromethane

: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
In methanol at 30℃; under 6750540 Torr; for 96h;	54%
In acetonitrile for 65h; Heating;	25%

: 22630-09-7
trimorpholylmethane

: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
With tetra-n-propyl-diborane	53%

: 110-91-8
morpholine

: 4432-43-3
N-hydroxymethylmorpholine

: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
at 25℃; Equilibrium constant;
With water; potassium carbonate

: 110-91-8
morpholine

: 50-00-0
formaldehyd

A: 7309-48-0
4-methoxymethyl-morpholine

B: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
With methanol; benzene

...Expand

: 7309-48-0
4-methoxymethyl-morpholine

: 41316-44-3
3-methyl-3-ethyloxaziridine

A: 5625-90-1
4-(morpholinomethyl)morpholine

B: 5824-79-3
methylene-morpholin-4-yl-amine

Conditions

Conditions	Yield
1) ether, benzene, 10 deg C, 24 h 2) evacuation, -10 deg C, one week;

...Expand

: 110-91-8
morpholine

: 50-00-0
formaldehyd

A: 4432-43-3
N-hydroxymethylmorpholine

B: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
at 70 - 80℃; for 2.33333h; Title compound not separated from byproducts.;
at 60℃; for 13h; Cooling with ice;
at 20 - 65℃; for 13h;

...Expand

: 110-91-8
morpholine

paraformaldehyde: paraformaldehyde

A: 4432-43-3
N-hydroxymethylmorpholine

B: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
at 70 - 80℃; for 2h;

...Expand

: 7529-22-8
4-methylmorpholine N-oxide

: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
With magnesium bis(N,N-diisopropylamide) In tetrahydrofuran for 1.25h; Inert atmosphere;

: 110-91-8
morpholine

: 50-00-0
formaldehyd

A: 4394-85-8
4-morpholinecarboxaldehyde

B: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
With sodium hydroxide In water at 25℃; for 6h; Concentration; Reagent/catalyst;

...Expand

: 110-91-8
morpholine

: 50-00-0
formaldehyd

A: 7309-48-0
4-methoxymethyl-morpholine

B: 4394-85-8
4-morpholinecarboxaldehyde

C: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
In water at 25℃; for 6h; Concentration; Reagent/catalyst;

...Expand

: 110-91-8
morpholine

: 124-38-9
carbon dioxide

A: 109-02-4
4-methyl-morpholine

B: 4394-85-8
4-morpholinecarboxaldehyde

C: 5625-90-1
4-(morpholinomethyl)morpholine

Conditions

Conditions	Yield
With diphenylsilane; [(2,6-(2,4,6-Me3C6H2)2C6H3)Ge(O)(1,3,4,5-tetramethylimidazol-2-ylidene)2]Cl In [D3]acetonitrile at 20℃; under 750.075 Torr; for 10h; Time; Reagent/catalyst; Temperature; Inert atmosphere;	A 35 %Spectr. B 22 %Spectr. C 32 %Spectr.

...Expand

: 5625-90-1
4-(morpholinomethyl)morpholine

: 52853-19-7
N-(methylene)morpholinium chloride

Conditions

Conditions	Yield
With acetyl chloride In diethyl ether for 2h;	100%
With acetyl chloride In diethyl ether at 20 - 24℃; for 2h;	94%
With acetyl chloride In diethyl ether

: 5625-90-1
4-(morpholinomethyl)morpholine

: 358-23-6
trifluoromethylsulfonic anhydride

: 1353747-69-9
N-methylenemorpholinium triflate

Conditions

Conditions	Yield
In diethyl ether at 20 - 24℃; for 3h;	99%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 121-69-7
N,N-dimethyl-aniline

A: 101-61-1
4,4'-methylene-bis(N,N-dimethylaniline)

B: 16158-90-0
4-(Morpholinomethyl)-N,N-dimethylaniline

Conditions

Conditions	Yield
With acetic acid at 35℃; for 2.08333h;	A 2% B 98%
With acetic acid at 35℃; for 2.08333h;	A 10% B 42%

...Expand

: 5625-90-1
4-(morpholinomethyl)morpholine

: 536-74-3
phenylacetylene

: 1017-73-8
4-(3-phenyl-prop-2-ynyl)-morpholine

Conditions

Conditions	Yield
With copper(l) chloride at 80℃; for 6h; Under argon;	98%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 110-66-7
n-pentanethiol

: 1394913-18-8
N-(pentylsulfanylmethyl)morpholine

Conditions

Conditions	Yield
With zinc(II) chloride dihydrate at 60℃; for 6h; Temperature; Reagent/catalyst; Time;	98%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 75-33-2
2-propanethiol

: N-(propan-2-ylsulfanylmethyl)morpholine

Conditions

Conditions	Yield
With samarium(III) chloride hexahydrate at 60℃; for 6h; Temperature; Reagent/catalyst; Time;	96%

: 5625-90-1
4-(morpholinomethyl)morpholine

: prop-2-ynyl {(1R,4aR,4bS,6R,6aR,12aR,12bS)-16-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6a,7,12,12a,13,14,14a-pentadecahydro2H(6,12b-etheno)benzo[b]chrysen-7,12-dion}-1-carboxylate

: [4-(morpholin-4-yl)but-2-ynyl] {(1R,4aR,4bS,6R,6aR,12aR,12bS)-16-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6a,7,12,12a,13,14,14a-pentadecahydro-2H-(6,12b-etheno)benzo[b]chrysen-7,12-dion}-1-carboxylate

Conditions

Conditions	Yield
With copper(l) chloride In 1,4-dioxane at 20℃; for 0.5h; Mannich Aminomethylation; Inert atmosphere;	96%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 60-80-0
antipyrine

: 101268-93-3
4-(N-morpholinylmethyl) antipyrine

Conditions

Conditions	Yield
In acetonitrile at 40℃; for 24h;	95%
With water

: 5625-90-1
4-(morpholinomethyl)morpholine

: 3-(prop-2-ynyl)-3H-benzo[e]perimidine-2,7-dione

: 3-(4-morpholinobut-2-yn-1-yl)-3H-benzo[e]perimidine-2,7-dione

Conditions

Conditions	Yield
With copper(l) chloride In 1,4-dioxane at 20℃; for 1h; Mannich Aminomethylation; Inert atmosphere;	95%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 4-phenylimino-2-(prop-2-ynyloxy)naphthalen-1(4H)-one

: 2-(4-morpholinobut-2-ynyloxy)-4-phenyliminonaphthalen-1(4H)-one

Conditions

Conditions	Yield
With copper(l) chloride In 1,4-dioxane at 20℃; for 1h; Inert atmosphere;	94%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 188935-64-0
bis(trimethylthylsilyl) 2-(pyrid-4-yl)ethylphosphonite

: trimethylsilyl (N-morpholinomethyl)[2-(4-pyridyl)ethyl]phosphinate

Conditions

Conditions	Yield
In dichloromethane Heating;	93%
zinc(II) chloride at 130℃;	93%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 42366-35-8
(E)-2-(Hydroxyimino)-N-phenylacetamid

: (E)-2-(Hydroxyimino)-3-morpholino-N-phenylpropanamid

Conditions

Conditions	Yield
In 1,4-dioxane for 0.666667h; Addition; Mannich reaction; Heating;	93%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 5335-28-4
phenyl-glyoxal-2-phenylhydrazone

: 110378-55-7
3-Morpholino-2-phenylhydrazonopropiophenon

Conditions

Conditions	Yield
In 1,4-dioxane for 0.666667h; Mannich reaction; Heating;	92%

: 26236-17-9
2,2,4,6-Tetrachloro-1,3,5,2λ5-triazaphosphorin

: 5625-90-1
4-(morpholinomethyl)morpholine

: 2,2-dichloro-4,6-di-morpholin-4-yl-2λ5-[1,3,5,2]triazaphosphinine

Conditions

Conditions	Yield
In toluene for 24h; Heating;	92%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 131526-95-9
9-hydroxy-7-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one

: 9-hydroxy-7-methyl-8-(morpholinomethyl)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one

Conditions

Conditions	Yield
In 1,4-dioxane at 100℃; Mannich reaction;	92%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 3722-44-9
3-hydroxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

: 17792-11-9
3-hydroxy-4-morpholinomethyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one

Conditions

Conditions	Yield
In 1,4-dioxane at 100℃; Mannich reaction;	91%

: 623-73-4
diazoacetic acid ethyl ester

: 5625-90-1
4-(morpholinomethyl)morpholine

: ethyl 2,3-dimorpholinopropanoate

Conditions

Conditions	Yield
With C32H34N2P2Pd(2+)*2F6P(1-) In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique;	91%
With zinc trifluoromethanesulfonate In 1,4-dioxane at 100℃; under 760.051 Torr; for 6h; Inert atmosphere;	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 75-36-5
acetyl chloride

: 16158-87-5
N-(chloromethyl)morpholine

Conditions

Conditions	Yield
	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 188935-62-8
C14H28NO2PSi2

: trimethylsilyl (N-morpholinomethyl)[2-(4-methyl-3-pyridyl)ethyl]phosphinate

Conditions

Conditions	Yield
In dichloromethane Heating;	90%
zinc(II) chloride at 130℃;	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 139399-43-2
7-hydroxy-3-(1-methyl-2-benzimidazolyl)-6-ethylchromone

: 6-ethyl-7-hydroxy-3-(1-methyl-1H-benzoimidazol-2-yl)-8-morpholin-4-ylmethyl-chromen-4-one

Conditions

Conditions	Yield
In 1,4-dioxane Heating;	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 532-54-7, 22668-53-7
E-isonitrosoacetophenone

: 100616-18-0
(E)-2-(Hydroxyimino)-3-morpholinopropiophenon

Conditions

Conditions	Yield
In 1,4-dioxane for 0.666667h; Addition; Mannich reaction; Heating;	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 58851-99-3
3-benzothiazol-2-yl-7-hydroxy-chromen-2-one

: 3-benzothiazol-2-yl-7-hydroxy-8-morpholin-4-ylmethyl-chromen-2-one

Conditions

Conditions	Yield
In 1,4-dioxane Heating;	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 1073-13-8
4,4-dimethylcyclohexenone

: 4,4-dimethyl-6-(morpholinomethyl)cyclohex-2-enone

Conditions

Conditions	Yield
With acetyl chloride In acetonitrile at 20℃; Mannich reaction;	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: C15H17N2O2(1+)*I(1-)

: 3,5-bis(morpholinomethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 4-(morpholinomethyl)morpholine; C15H17N2O2(1+)*I(1-) In acetonitrile at 90℃; for 8h; Mannich Aminomethylation; Stage #2: With acetic acid; zinc In acetonitrile at 20℃; for 0.0833333h;	90%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 3663-52-3
bis(trimethylsilyl) phosphonate

: C13H29N2O4PSi

Conditions

Conditions	Yield
With zinc(II) chloride at 90℃; for 1.5h;	89%

: 5625-90-1
4-(morpholinomethyl)morpholine

: 53391-78-9
2-chloro-3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one

: 2-chloro-3-hydroxy-4-morpholinomethyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one

Conditions

Conditions	Yield
In 1,4-dioxane at 100℃; Mannich reaction;	89%

N,N'-Dimorpholinomethane Chemical Properties

Molecular Formula of N,N'-Dimorpholinomethane (CAS NO.5625-90-1): C₉H₁₈N₂O₂
Molecular Weight: 186.25142g/mol
EINECS: 227-062-3
Index of Refraction: 1.496
Density: 1.09 g/cm³
Flash Point: 77.6 °C
Enthalpy of Vaporization: 50.3 kJ/mol
Boiling Point: 265.1 °C at 760 mmHg
Vapour Pressure: 0.00935 mmHg at 25 °C
Structure of N,N'-Dimorpholinomethane (CAS NO.5625-90-1):

IUPAC Name: 4-(Morpholin-4-ylmethyl)morpholine

N,N'-Dimorpholinomethane Toxicity Data With Reference

scu-rat LD50:1000 mg/kg

ZEKBAI Zeitschrift fuer Krebsforschung. 71 (1968),105.

N,N'-Dimorpholinomethane Safety Profile

Moderately toxic by subcutaneous route. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of NO_x.
The Hazard Codes of N,N'-Dimorpholinomethane (CAS NO.5625-90-1): Xi, F
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.

N,N'-Dimorpholinomethane Specification

N,N'-Dimorpholinomethane , its cas register number is 5625-90-1. It also can be called N,N'-Methylenebismorpholine ; Morpholine, 4,4'-methylenebis- ; and Bismorpholino methane .

Product Name

N,N'-Dimorpholinomethane

Synthetic route

N,N'-Dimorpholinomethane Chemical Properties

N,N'-Dimorpholinomethane Toxicity Data With Reference

N,N'-Dimorpholinomethane Safety Profile

N,N'-Dimorpholinomethane Specification

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