N-Acryloylmorpholine
Conditions | Yield |
---|---|
With 10H-phenothiazine; sodium methylate In glycerol at 200℃; Pyrolysis; | 97% |
(+/-)-2-hydroxy-1-morpholinopropan-1-one
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With sulfuric acid; acetic anhydride at 550℃; Temperature; | 96.1% |
4-(3-methoxy-propionyl)-morpholine
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With sodium methylate; 4-methoxy-phenol at 200℃; Pyrolysis; | 96% |
With lithium phosphate at 390℃; Pyrolysis; |
β-morpholinyl-N,N-morpholinylpropionic acid amide
acetic anhydride
A
4-acetylmorpholine
B
N-Acryloylmorpholine
Conditions | Yield |
---|---|
Stage #1: β-morpholinyl-N,N-morpholinylpropionic acid amide; acetic anhydride In toluene at 20 - 80℃; for 2h; Inert atmosphere; Stage #2: With 2,6-di-tert-butyl-4-methyl-phenol; N-ethyl-N,N-diisopropylamine for 18h; Reagent/catalyst; Temperature; Reflux; | A 84% B 95% |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
Stage #1: 3-(diethylamino)-1-morpholinopropan-1-one With acetic anhydride In toluene at 20 - 80℃; for 2h; Inert atmosphere; Stage #2: With 2,6-di-tert-butyl-4-methyl-phenol; triethylamine Reflux; | 94% |
With 4-methoxy-phenol | 11.8 g |
Conditions | Yield |
---|---|
With 10H-phenothiazine; sulfuric acid for 2h; Reagent/catalyst; Heating; | 93.12% |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With 10H-phenothiazine; sodium methylate; 4-methoxy-phenol In glycerol at 160℃; Pyrolysis; | 92% |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 78℃; for 5h; Temperature; | 91.5% |
1-morpholinopropane-1-one
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With potassium tert-butylate; oxygen; palladium diacetate In dimethyl sulfoxide at 90 - 120℃; under 760.051 Torr; for 36h; Reagent/catalyst; Temperature; | 90% |
Conditions | Yield |
---|---|
With triethylamine at 0 - 3℃; for 2h; Reagent/catalyst; Temperature; | 89.95% |
Conditions | Yield |
---|---|
With 10H-phenothiazine; copper(II) bis(trifluoromethanesulfonate) at 135℃; for 2h; Inert atmosphere; | 89% |
With 4-methoxy-phenol | 8.46 g |
With 10H-phenothiazine; sulfuric acid; 4-methoxy-phenol at 180 - 220℃; under 450.045 Torr; for 6h; Reagent/catalyst; | |
With 10H-phenothiazine In glycerol at 150℃; under 52.5053 Torr; for 0.5h; Reagent/catalyst; Solvent; Inert atmosphere; |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 85℃; for 3h; | 88.7% |
Conditions | Yield |
---|---|
With sodium hydroxide at 85 - 90℃; | 85.5% |
With potassium tert-butylate In water at 120℃; for 3h; Reagent/catalyst; Temperature; | 20.7% |
β-morpholinyl-N,N-morpholinylpropionic acid amide
benzyl bromide
A
N-Acryloylmorpholine
B
4-benzyl-morpholine
Conditions | Yield |
---|---|
Stage #1: β-morpholinyl-N,N-morpholinylpropionic acid amide; benzyl bromide In toluene at 20 - 80℃; for 2h; Inert atmosphere; Stage #2: With 2,6-di-tert-butyl-4-methyl-phenol; triethylamine for 12h; Reflux; | A 77% B 84% |
Conditions | Yield |
---|---|
With 4-methoxy-phenol; trichlorophosphate In dichloromethane at 0 - 5℃; for 1h; Reagent/catalyst; Concentration; Solvent; | 81% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; | 21% |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate); hydroquinone at 100℃; for 10h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane 1 h, 0 deg C then 1 h, room temp.; | 78% |
With triethylamine 1.) 0 deg C, 1 h; 2.) r.t., 1 h; | 78% |
In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 63% |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With phosphorus pentoxide In N,N-dimethyl-formamide at 135℃; Temperature; Solvent; | 77.6% |
Conditions | Yield |
---|---|
In dichloromethane 1.) 0 deg C, 483 min; 2.) 25 deg C, 1 h; | 76% |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; for 16h; | 75% |
Conditions | Yield |
---|---|
With sulfuric acid at 120℃; for 3h; Inert atmosphere; | 28.2% |
morpholine
acryloyl chloride
A
N-Acryloylmorpholine
B
β-morpholinyl-N,N-morpholinylpropionic acid amide
Conditions | Yield |
---|---|
With triethylamine; benzene |
Conditions | Yield |
---|---|
With tetracarbonyl nickel; acrylic acid; toluene |
Conditions | Yield |
---|---|
With triethylamine In ethanol for 1h; Heating; | A 40 % Chromat. B 60 % Chromat. |
N-prop-2-ynylmorpholine N-oxide
A
morpholine
B
N-Acryloylmorpholine
C
N-propargylmorpholine
D
3-(3-oxapentane-1,5-diyl)aminoacrylaldehyde
Conditions | Yield |
---|---|
With triethylamine In tert-butyl alcohol at 50 - 79℃; Product distribution; Activation energy; Kinetics; Further Variations:; Solvents; Temperatures; Reagents; pH-values; |
2-chloro-1-(4-morpholino)propan-1-one
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 70℃; for 8h; | 569 g |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With 4-methoxy-phenol | 19.2 g |
morpholine
acrylic acid methyl ester
acrylic acid
N-Acryloylmorpholine
Conditions | Yield |
---|---|
Stage #1: morpholine; acrylic acid methyl ester With 2,6-di-tert-butyl-4-methyl-phenol at 20 - 55℃; for 3h; Inert atmosphere; Stage #2: With sodium methylate In methanol at 55 - 75℃; for 6.5h; Stage #3: acrylic acid With 2,6-di-tert-butyl-4-methyl-phenol In 5,5-dimethyl-1,3-cyclohexadiene at 140 - 145℃; for 2h; |
S-1-butyl-S'-(α-methyl-α'-acetic acid)trithiocarbonate
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride In 1,4-dioxane; water at 70℃; for 2h; Inert atmosphere; | 99% |
With 4,4'-dicyano-4,4'-azo-di-valeric acid In 1,4-dioxane; water at 70℃; for 24h; |
pyrrolidine
N-Acryloylmorpholine
1-morpholino-3-(pyrrolidin-1-yl)propan-1-one
Conditions | Yield |
---|---|
In dichloromethane for 1h; Inert atmosphere; Reflux; | 98% |
With [DABCO-PDO][OAc] In neat (no solvent) at 20℃; for 2h; Michael Addition; Green chemistry; | 90% |
With triethylamine In water at 20℃; for 2h; Michael Addition; Green chemistry; | 89% |
N-Acryloylmorpholine
3-chloro-8-methyl-6-trifluoromethylsulfonyloxy-8H-quino[4,3,2-kl]acridine
(E)-3-(3-chloro-8-methyl-8H-quino[4,3,2-kl]acridin-6-yl)acrylic acid (morpholin-1-yl)amide
Conditions | Yield |
---|---|
With triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 18h; Heck reaction; | 98% |
Conditions | Yield |
---|---|
With C29H26N2O5Ru; sodium acetate In 1,4-dioxane at 100℃; for 96h; Inert atmosphere; | 98% |
N-Acryloylmorpholine
5,5'-dibromo-2,2'-bisthiophene
4,4′-{2,2′-bithiene-5,5′-diylbis-[(1E)-3-oxoprop-1-ene-1,3-diyl]}dimorpholine
Conditions | Yield |
---|---|
With dichloro{bis[1,1’,1’’-(phosphinetriyl)tripiperidine]}palladium(II); tetrabutylammomium bromide; potassium carbonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Heck Reaction; Schlenk technique; Glovebox; Inert atmosphere; Green chemistry; | 98% |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With C33H30N2O In dichloromethane at -78 - -30℃; for 44h; Michael Addition; Inert atmosphere; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; N,N'-bis(2,6-dimethylphenyl)butane-2,3-diimine; toluene-4-sulfonic acid; p-benzoquinone In tetrahydrofuran at 20℃; under 3000.3 Torr; for 67h; Autoclave; | 98% |
N-Acryloylmorpholine
Conditions | Yield |
---|---|
In tetrahydrofuran | 97% |
Conditions | Yield |
---|---|
With copper(l) iodide; N,N,N',N'',N'''-pentamethyldiethylenetriamine In acetonitrile at 80℃; for 12h; Schlenk technique; Inert atmosphere; stereoselective reaction; | 97% |
Conditions | Yield |
---|---|
With potassium tert-butylate In neat (no solvent) at 20℃; for 0.333333h; Michael Addition; Inert atmosphere; | 96% |
tert-butyl 5-iodo-1H-indole-1-carboxylate
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With potassium phosphate; sodium chloride In water; N,N-dimethyl-formamide at 45℃; for 16h; Micellar solution; | 96% |
Conditions | Yield |
---|---|
at 70 - 100℃; for 3.16667h; | 95% |
N-Acryloylmorpholine
1-Bromonaphthalene
(E)-1-morpholino-3-(naphthalen-1-yl)prop-2-en-1-one
Conditions | Yield |
---|---|
With dichloro{bis[1,1’,1’’-(phosphinetriyl)tripiperidine]}palladium(II); tetrabutylammomium bromide; potassium carbonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 6h; Heck Reaction; Schlenk technique; Glovebox; Inert atmosphere; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With potassium tert-butylate In neat (no solvent) at 20℃; for 0.333333h; Michael Addition; Inert atmosphere; | 95% |
N-Acryloylmorpholine
4-Bromodiphenyl ether
(E)-1-morpholino-3-(4-phenoxyphenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
With dichloro{bis[1,1’,1’’-(phosphinetriyl)tripiperidine]}palladium(II); tetrabutylammomium bromide; potassium carbonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Heck Reaction; Schlenk technique; Glovebox; Inert atmosphere; Green chemistry; | 94% |
3-phenyl-4-iodo-5-methylisoxazole
N-Acryloylmorpholine
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; sodium carbonate; palladium diacetate In N,N-dimethyl-formamide at 85℃; for 24h; Heck cross-coupling; | 93% |
N-Acryloylmorpholine
tert-butyl 4-(4-chloro-2-methoxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate
tert-butyl 4-{2-methoxy-4-[(1E)-3-morpholin-4-yl-3-oxoprop-1-enyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate
Conditions | Yield |
---|---|
With N-Methyldicyclohexylamine; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In 1,4-dioxane at 120℃; | 93% |
N-Acryloylmorpholine
diethyl (N-benzylideneaminomethyl)phosphonate
diethyl ((2S,4S,5S)-4-(morpholine-4-carbonyl)-5-phenylpyrrolidine-2-yl)phosphonate
Conditions | Yield |
---|---|
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; silever triflate; potassium hexamethylsilazane In toluene at 25℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 93% |
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; silver bis(trimethylsilyl)amide In toluene at 25℃; for 2h; Inert atmosphere; optical yield given as %ee; stereoselective reaction; | 93% |
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; silver bis(trimethylsilyl)amide In toluene at 25℃; enantioselective reaction; | 93% |
Conditions | Yield |
---|---|
With copper(l) iodide; benzyl tri-n-butylammonium bromide; tris[(2-pyridylmethyl)amine]; diisopropylamine In toluene at 100℃; for 20h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tetramethylammonium formiate; P(p-C6H4F)3 In 1,4-dioxane; water at 80℃; for 4h; Sealed tube; | 93% |
N-Acryloylmorpholine
3-chloro-8-methyl-8H-quino[4,3,2-kl]acridine
(E)-3-(8-methyl-8H-quino[4,3,2-kl]acridin-3-yl)acrylic acid (morpholin-4-yl)amide
Conditions | Yield |
---|---|
With potassium phosphate; tri-tert-butyl phosphine; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 170℃; for 48h; Heck reaction; | 92% |
N-Acryloylmorpholine
methyl 2-(benzylideneamino)acetate
(2R,4S,5S)-methyl 4-(morpholine-4-carbonyl)-5-phenylpyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With (R)-DTBM-segphos; silver trifluoromethanesulfonate; potassium hexamethylsilazane In diethyl ether at 0℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 92% |
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; silver bis(trimethylsilyl)amide In diethyl ether at 0℃; for 24h; Inert atmosphere; optical yield given as %ee; stereoselective reaction; | 92% |
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; silver bis(trimethylsilyl)amide In diethyl ether at 0℃; for 24h; enantioselective reaction; | 92% |
N-Acryloylmorpholine
3-((7-chloro-3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one
(E)-3-((7-chloro-3-(3-morpholino-3-oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one
Conditions | Yield |
---|---|
Stage #1: N-Acryloylmorpholine; 3-((7-chloro-3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one With triphenylphosphine; palladium diacetate In tetrahydrofuran at 80℃; for 2h; Inert atmosphere; Stage #2: With water for 1h; | 92% |
The molecular structure of 2-Propen-1-one,1-(4-morpholinyl)- (CAS NO.5117-12-4) is
IUPAC Name: 1-Morpholin-4-ylprop-2-en-1-one
Canonical SMILES: C=CC(=O)N1CCOCC1
Molecular Formula: C7H11 N O2
Molecular Weight: 141.17
Density: 1.074 g/cm3
Melting Point: -35 ºC
Boiling Point: 296.8 °C at 760 mmHg
Flash Point: 133.3 °C
Freely Rotating Bonds: 1
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.477
Molar Refractivity: 37.18 cm3
Molar Volume: 131.4 cm3
Polarizability: 14.74× 10-24 cm3
Surface Tension: 35.9 dyne/cm
Enthalpy of Vaporization: 53.66 kJ/mol
Vapour Pressure: 0.00141 mmHg at 25°C
The Cas Register Number of 2-Propen-1-one,1-(4-morpholinyl)- is 5117-12-4. The chemical synonyms of 2-Propen-1-one,1-(4-morpholinyl)- (CAS NO.5117-12-4) are Acryloyl morpholine;4-Acryloylmorpholine ; N-Acryloylmorpholine ; 4-(1-Oxo-2-propenyl)-Morpholine ; N-Acrolylmorpholine ; N-Acrylylmorpholine ; 4-Acryloylmorpholine,98+% ; Morpholine, 4-(1-oxo-2-propenyl)- . Its product categories are Acrylate ; Acrylic Monomers ; Monomers .
2-Propen-1-one,1-(4-morpholinyl)- (CAS NO.5117-12-4) isused as pharmaceutical intermediate.
Hazard Codes: Xn
Risk Statements: 22-41-43-48/22
R22: Harmful if swallowed.
R41: Risk of serious damage to the eyes.
R43: May cause sensitization by skin contact.
R48/22: Harmful: danger of serious damage to health by prolonged exposure if swallowed.
Safety Statements: 23-26-36/37/39
S23: Do not breathe vapour.
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.
WGK Germany: 2
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