Product Name

  • Name

    N-Formylmorpholine

  • EINECS 224-518-3
  • CAS No. 4394-85-8
  • Article Data242
  • CAS DataBase
  • Density 1.21 g/cm3
  • Solubility soluble in water
  • Melting Point 23 °C(lit.)
  • Formula C5H9NO2
  • Boiling Point 236.5 °C at 760 mmHg
  • Molecular Weight 115.132
  • Flash Point 107 °C
  • Transport Information
  • Appearance clear yellow liquid
  • Safety 23-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 4394-85-8 (N-Formylmorpholine)
  • Hazard Symbols
  • Synonyms 4-Formylmorpholine;Morpholine, 4-formyl-;N-Morpholinecarboxaldehyde;NSC 14833;
  • PSA 29.54000
  • LogP 0.04880

Synthetic route

morpholine
110-91-8

morpholine

formic acid
64-18-6

formic acid

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 3h; Reagent/catalyst; Solvent;100%
In butan-1-ol at 120℃; Solvent; Temperature;99.35%
In ethanol at 140℃; for 24h; Solvent; Autoclave;98%
morpholine
110-91-8

morpholine

formamide
77287-34-4, 77287-35-5, 60100-09-6

formamide

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate In toluene for 7h; Reflux;100%
With water; boric acid at 100℃; for 24h;87%
With [bis(acetoxy)iodo]benzene In neat (no solvent) at 100℃; for 0.333333h; Microwave irradiation; Green chemistry;86%
lithium morpholide
37828-58-3

lithium morpholide

carbon monoxide
201230-82-2

carbon monoxide

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With water In tetrahydrofuran at 0℃; under 759.8 Torr;100%
In tetrahydrofuran at 0℃; Product distribution; with/without n-BuLi reag.; various inhibitors;
morpholine
110-91-8

morpholine

carbon dioxide
124-38-9

carbon dioxide

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With phenylsilane; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In tetrahydrofuran-d8 at 100℃; under 750.075 Torr; for 6h; Inert atmosphere;100%
With C21H24N2; phenylsilane In tetrahydrofuran at 20℃; under 750.075 - 2250.23 Torr; for 0.25h; Reagent/catalyst; Solvent; Temperature; Time; Concentration; Inert atmosphere; Glovebox;100%
With phenylsilane at 25℃; under 3750.38 Torr; for 12h; Pressure; Temperature; Autoclave;100%
morpholine
110-91-8

morpholine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With 1,2,4-Triazole; 8-quinolinol; copper(II) choride dihydrate at 150℃; Reagent/catalyst; Temperature;98%
With zinc(II) phthalocyanine; carbon dioxide; phenylsilane at 25℃; under 3750.38 Torr; for 6h; Autoclave; chemoselective reaction;92%
Stage #1: N,N-dimethyl-formamide With bis(2-chlorophenyl)borinic acid; acetic acid at 65℃; for 0.25h; Inert atmosphere;
Stage #2: morpholine at 65℃; for 24h; Inert atmosphere;		89%
morpholine
110-91-8

morpholine

formaldehyd
50-00-0

formaldehyd

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 6h;97%
With potassium iodide In water Ambient temperature; electrolysis;83%
With oxygen; sodium hydroxide In tetrahydrofuran; water at 10℃; for 23h;75%
morpholine
110-91-8

morpholine

Isopropenyl formate
32978-00-0

Isopropenyl formate

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
In ethyl acetate for 1h; Ambient temperature;97%
4-((Z)-2-Methyl-undec-1-enyl)-morpholine

4-((Z)-2-Methyl-undec-1-enyl)-morpholine

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

methyl nonyl ketone
112-12-9

methyl nonyl ketone

Conditions
ConditionsYield
With oxygen; Cu-X zeolite In 1,2-dichloro-ethane; acetonitrile at 50℃; for 5h; Oxidation; Oxidative cleavage;A 96%
B 97%
morpholine
110-91-8

morpholine

Methyl formate
107-31-3

Methyl formate

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With calcium(II) bis(trifluoromethanesulfonyl)imide In neat (no solvent) at 115℃; for 1h; Microwave irradiation; Sealed tube;96%
With methanol at 140℃; for 16h; Reagent/catalyst;92.7%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 20℃; for 0.5h;90%
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amide](carbonyl)(hydride)iron(II) In tetrahydrofuran at 80℃; for 8h; Catalytic behavior; Mechanism; Reagent/catalyst; Schlenk technique; Sealed tube; Inert atmosphere;
morpholine
110-91-8

morpholine

carbon monoxide
201230-82-2

carbon monoxide

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium In tetrahydrofuran at 185℃; for 24h;95.5%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 100℃; under 22502.3 Torr; for 20h; Autoclave;83%
With potassium hydroxide In methanol at 110℃; under 7500.75 Torr; for 15h; Autoclave;76%
morpholine
110-91-8

morpholine

chloroform
67-66-3

chloroform

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With sodium ethanolate at 50℃; Riemer-Tiemann reaction; Inert atmosphere;95%
With potassium fluoride on basic alumina In acetonitrile at 20℃; for 18h;80%
With sodium hydroxide; tetrabutyl ammonium fluoride at 50℃; for 2.08333h;35%
1-(4-morpholino)-2,2-diphenylethene
61253-71-2

1-(4-morpholino)-2,2-diphenylethene

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

benzophenone
119-61-9

benzophenone

Conditions
ConditionsYield
With oxygen; copper dichloride In 1,2-dichloro-ethane; acetonitrile at 50℃; for 1h; Oxidation; Oxidative cleavage;A 95%
B 87%
With aluminum oxide; potassium permanganate; neutral In acetone for 4h; Ambient temperature;A n/a
B 75%
morpholine
110-91-8

morpholine

ammonium formate
16712-16-6, 64165-14-6, 65387-22-6, 70179-79-2, 540-69-2

ammonium formate

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
In acetonitrile for 10h; Formylation;95%
morpholine
110-91-8

morpholine

carbon dioxide
124-38-9

carbon dioxide

A

4-methyl-morpholine
109-02-4

4-methyl-morpholine

B

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With tris(2-diphenylphosphinoethyl)phosphine; hydrogen; potassium carbonate; cobalt(II) perchlorate hexahydrate In ethanol at 140℃; under 45004.5 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Green chemistry;A 1%
B 95%
With tris(2-diphenylphosphinoethyl)phosphine; hydrogen; potassium carbonate; cobalt(II) perchlorate hexahydrate In ethanol at 120℃; under 45004.5 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Green chemistry;A 10%
B 79%
With potassium phosphate; tris(2-diphenylphosphinoethyl)phosphine; hydrogen; cobalt(II) perchlorate hexahydrate In tetrahydrofuran at 140℃; under 45004.5 Torr; for 24h; Catalytic behavior; Mechanism; Time; Reagent/catalyst; Temperature; Pressure; Autoclave; Green chemistry;A 69%
B 28%
With C27H36Cl2N2Zn; phenylsilane at 100℃; for 20h;
With diphenylsilane; [(2,6-(2,4,6-Me3C6H2)2C6H3)Ge(O)(1,3,4,5-tetramethylimidazol-2-ylidene)2]Cl In [D3]acetonitrile at 50℃; under 750.075 Torr; for 3h; Time; Inert atmosphere;A 75 %Spectr.
B 21 %Spectr.
...Expand
N-cyanomorpholine
1530-89-8

N-cyanomorpholine

acetic acid
64-19-7

acetic acid

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

4-acetylmorpholine
1696-20-4

4-acetylmorpholine

Conditions
ConditionsYield
With zinc for 2h; Heating;A 6%
B 94%
...Expand
N-cyanomorpholine
1530-89-8

N-cyanomorpholine

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

4-acetylmorpholine
1696-20-4

4-acetylmorpholine

Conditions
ConditionsYield
With acetic acid; zinc for 2h; Heating;A 6%
B 94%
4-(2-methyl-1-propenyl)morpholine
2403-55-6

4-(2-methyl-1-propenyl)morpholine

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

acetone
67-64-1

acetone

Conditions
ConditionsYield
With oxygen; Cu-X zeolite In 1,2-dichloro-ethane; acetonitrile at 50℃; for 5h; Oxidation; Oxidative cleavage;A 93%
B n/a
1,2-dimorpholylethane
1723-94-0

1,2-dimorpholylethane

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; water; oxygen; silica gel; caesium carbonate In acetonitrile at 20℃; for 60h; Inert atmosphere; Irradiation;93%
4-((E)-2,6-Dimethyl-hepta-1,5-dienyl)-morpholine

4-((E)-2,6-Dimethyl-hepta-1,5-dienyl)-morpholine

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate; neutral In acetone for 4h; Ambient temperature;A n/a
B 92%
3-(4-isopropyl)-phenyl-2-methyl-1-(4-morpholino)-1-propene

3-(4-isopropyl)-phenyl-2-methyl-1-(4-morpholino)-1-propene

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

1-(4-isopropylphenyl)propan-2-one
7306-39-0

1-(4-isopropylphenyl)propan-2-one

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate; neutral In acetone for 4h; Ambient temperature;A n/a
B 91%
morpholine
110-91-8

morpholine

formic acid ethyl ester
109-94-4

formic acid ethyl ester

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With Novozyme 435 CALB In tetrahydrofuran at 20℃; Green chemistry; Enzymatic reaction;91%
With o-toluenesulfonic acid at 55℃; for 4h;88%
With toluene-4-sulfonic acid at 60℃; for 24h;56%
at 65℃; for 12h; Inert atmosphere;
at 60℃; for 24h;
morpholine
110-91-8

morpholine

[((η5-C5H3)2(SiMe2)2)Ru2(μ-D)(CO)4]OSO2CF3

[((η5-C5H3)2(SiMe2)2)Ru2(μ-D)(CO)4]OSO2CF3

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

[(η5-C5H3)2(Si(CH3)2)2]Ru2(CO)4
287097-09-0

[(η5-C5H3)2(Si(CH3)2)2]Ru2(CO)4

C

[(η5-C5H3)2(SiMe2)2]Ru2(CO)3(morpholine)
287097-16-9

[(η5-C5H3)2(SiMe2)2]Ru2(CO)3(morpholine)

Conditions
ConditionsYield
With triphenylmethane In benzene-d6 Kinetics; amine was added to a soln. in C6D6 in NMR tube for 5 min (Ar); not sepd., detected by NMR spectra;A 91%
B 5%
C n/a
...Expand
morpholine
110-91-8

morpholine

Hex-1-en-2-yl formate
134965-38-1

Hex-1-en-2-yl formate

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
In ethyl acetate for 1h; Ambient temperature;90%
4-(2-phenyl-propenyl)-morpholine
28478-27-5

4-(2-phenyl-propenyl)-morpholine

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate; neutral In acetone for 4h; Ambient temperature;A n/a
B 90%
With aluminum oxide; potassium permanganate In acetone for 4h; Product distribution; Ambient temperature; reactions of derivatives, under var. conditions;A n/a
B 90%
4-[(1H-imidazol-1-yl)carbonyl]morpholine
93605-74-4

4-[(1H-imidazol-1-yl)carbonyl]morpholine

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃;90%
4-methyl-morpholine
109-02-4

4-methyl-morpholine

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With [2,2]bipyridinyl; C10H16NO; copper(II) bis(trifluoromethanesulfonate); copper(l) chloride In acetonitrile at 20℃; for 6h;90%
4-((trimethylsilyl)methyl)morpholine
54600-30-5

4-((trimethylsilyl)methyl)morpholine

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 25℃; for 4h; chemoselective reaction;86%
4-(2-methyl-undec-1-enyl)-morpholine
28478-28-6

4-(2-methyl-undec-1-enyl)-morpholine

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

methyl nonyl ketone
112-12-9

methyl nonyl ketone

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate; neutral In acetone for 4h; Ambient temperature;A n/a
B 84%
1-(4-morpholino)-2-phenylpropene
39166-22-8

1-(4-morpholino)-2-phenylpropene

A

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

B

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
With oxygen; Cu-X zeolite In 1,2-dichloro-ethane; acetonitrile at 50℃; for 5h; Oxidation; Oxidative cleavage;A 70%
B 84%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

dimethyl sulfate
77-78-1

dimethyl sulfate

4-(Methoxymethylene)-morpholinium methyl sulfate
5780-15-4

4-(Methoxymethylene)-morpholinium methyl sulfate

Conditions
ConditionsYield
at 60 - 70℃; for 3h;100%
at 70℃; for 2h;
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

3-bromo-4,5-bis(trimethylsilylethynyl)toluene
350600-10-1

3-bromo-4,5-bis(trimethylsilylethynyl)toluene

2,3-bis(trimethylsilylethynyl)-5-methylbenzaldehyde
350600-11-2

2,3-bis(trimethylsilylethynyl)-5-methylbenzaldehyde

Conditions
ConditionsYield
With sec.-butyllithium In tetrahydrofuran; diethyl ether at -78℃;100%
2-(4-isopropoxyphenoxy)thiazole
929118-32-1

2-(4-isopropoxyphenoxy)thiazole

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

2-(4-isopropoxyphenoxy)thiazole-5-carbaldehyde
929118-34-3

2-(4-isopropoxyphenoxy)thiazole-5-carbaldehyde

Conditions
ConditionsYield
Stage #1: 2-(4-isopropoxyphenoxy)thiazole With n-butyllithium In tetrahydrofuran at -78℃; for 1.25h;
Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78℃; for 4h; Further stages.;		100%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

4-thioformylmorpholine
5780-30-3

4-thioformylmorpholine

Conditions
ConditionsYield
With Lawessons reagent In dichloromethane at 20℃; for 3h;99%
With tetraphosphorus decasulfide In diethyl ether at 0 - 20℃; for 3h;80%
With tetraphosphorus decasulfide78.9%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

(E)-4-methyl-N-(morpholinomethylene)benzenesulfonamide
15294-84-5

(E)-4-methyl-N-(morpholinomethylene)benzenesulfonamide

Conditions
ConditionsYield
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction;99%
With thionyl chloride In chloroform at 60℃; for 3h;87%
With tert.-butylhydroperoxide; sodium iodide In water at 90℃; for 3h;52%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

para-chlorotoluene
106-43-4

para-chlorotoluene

4-(4-methylphenyl)morpholine
3077-16-5

4-(4-methylphenyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;99%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

chlorobenzene
108-90-7

chlorobenzene

4-Phenylmorpholine
92-53-5

4-Phenylmorpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;99%
With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate In water; toluene at 35℃; for 10h; Glovebox; Sealed tube; Inert atmosphere;90%
3-Chloropyridine
626-60-8

3-Chloropyridine

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

N-(3-pyridyl)morpholine
92670-29-6

N-(3-pyridyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

4-(pyridin-2-yl)morpholine
24255-25-2

4-(pyridin-2-yl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;99%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-chloromethyl-3-methyl-benzene
620-19-9

1-chloromethyl-3-methyl-benzene

4-(3-methylbenzyl)morpholine
90754-64-6

4-(3-methylbenzyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;99%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;80%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-chloromethyl-2-methylbenzene
552-45-4

1-chloromethyl-2-methylbenzene

4-(2-methylbenzyl)morpholine
51180-64-4

4-(2-methylbenzyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;99%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;81%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

4-(4-methoxy-benzyl)-morpholine
17494-29-0

4-(4-methoxy-benzyl)-morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;99%
With potassium hydroxide In water at 80℃; for 3h; Temperature; Green chemistry;90%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

m-methoxybenzyl chloride
824-98-6

m-methoxybenzyl chloride

4-[(3-methoxyphenyl)methyl]morpholine
122439-14-9

4-[(3-methoxyphenyl)methyl]morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;99%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;90%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

2-cyanobenzyl chloride
612-13-5

2-cyanobenzyl chloride

2-(morpholin-4-ylmethyl)benzonitrile
37812-33-2

2-(morpholin-4-ylmethyl)benzonitrile

Conditions
ConditionsYield
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;99%
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;98%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

(3-methylphenyl)-4-morpholinylmethanethione

(3-methylphenyl)-4-morpholinylmethanethione

Conditions
ConditionsYield
With sulfur; sodium carbonate; triethylamine In water at 120℃; for 12h; Inert atmosphere; Sealed tube;99%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

N-(4-methoxy-thiobenzoyl)-morpholine
6392-01-4

N-(4-methoxy-thiobenzoyl)-morpholine

Conditions
ConditionsYield
With sulfur; sodium carbonate; triethylamine In water at 120℃; for 12h; Schlenk technique; Inert atmosphere;99%
With sulfur; sodium carbonate; triethylamine In water at 120℃; for 12h; Inert atmosphere; Sealed tube;96%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

2-(2-chloro-4-methoxyphenoxy)-1,3-thiazole-5-carbaldehyde
946884-30-6

2-(2-chloro-4-methoxyphenoxy)-1,3-thiazole-5-carbaldehyde

Conditions
ConditionsYield
Stage #1: 2-(2-chloro-4-methoxyphenoxy)-1,3-thiazole With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.16667h;
Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran; hexanes at -78 - 25℃; for 1.08333h; Product distribution / selectivity;		98%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

4-(3-methoxyphenyl)morpholine
32040-09-8

4-(3-methoxyphenyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;98%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-chloro-3-methylbenzene
108-41-8

1-chloro-3-methylbenzene

4-m-tolylmorpholine
7025-91-4

4-m-tolylmorpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;98%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

4-tert-butylbenzyl chloride
19692-45-6

4-tert-butylbenzyl chloride

4-(4-(tert-butyl)benzyl)morpholine

4-(4-(tert-butyl)benzyl)morpholine

Conditions
ConditionsYield
With potassium hydroxide In water at 100℃; for 3h; Temperature; Green chemistry;98%
With NHC-Pd(II)-Im; sodium hydroxide In water at 80℃; for 3h; Temperature; Inert atmosphere; Schlenk technique;94%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

4-cyanobenzyl chloride
874-86-2

4-cyanobenzyl chloride

4-(morpholin-4-ylmethyl)benzonitrile
37812-51-4

4-(morpholin-4-ylmethyl)benzonitrile

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;98%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;92%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

4-nitrobenzyl chloride
100-14-1

4-nitrobenzyl chloride

4-(4-nitrobenzyl)morpholine
6425-46-3

4-(4-nitrobenzyl)morpholine

Conditions
ConditionsYield
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;98%
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;97%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

4-(4'-chloro-benzyl)morpholine
6425-43-0

4-(4'-chloro-benzyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;98%
With potassium hydroxide In water at 80℃; for 3h; Temperature; Green chemistry;93%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-chloro-2-(chloromethyl)benzene
611-19-8

1-chloro-2-(chloromethyl)benzene

2-(morpholinomethyl)chlorobenzene
415932-72-8

2-(morpholinomethyl)chlorobenzene

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;98%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;96%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

4-(naphthalene-1-ylmethyl)morpholine
2862-82-0

4-(naphthalene-1-ylmethyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;98%
With potassium hydroxide In water at 80℃; for 3h; Temperature; Green chemistry;87%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

4-Methylbenzyl chloride
104-82-5

4-Methylbenzyl chloride

4-(4-methylbenzyl)morpholine
46340-40-3

4-(4-methylbenzyl)morpholine

Conditions
ConditionsYield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;98%
With potassium hydroxide In water at 80℃; for 3h; Temperature; Green chemistry;96%

N-Formylmorpholine Consensus Reports

Reported in EPA TSCA Inventory.

N-Formylmorpholine Specification

The IUPAC name of 4-Formylmorpholine is morpholine-4-carbaldehyde. With the CAS registry number 4394-85-8, it is also named as 4-Morpholinecarbaldehyde. The classification codes are Skin / Eye Irritant; TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. It is clear yellow liquid which is soluble in alcohol and ether. In addition, this chemical is stable under normal temperature and pressure. Moreover, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.3; (4)ACD/LogD (pH 7.4): -1.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 4.67; (8)ACD/KOC (pH 7.4): 4.67; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 30.22 cm3; (14)Molar Volume: 95.1 cm3; (15)Polarizability: 11.98×10-24 cm3; (16)Surface Tension: 52.5 dyne/cm; (17)Enthalpy of Vaporization: 47.33 kJ/mol; (18)Vapour Pressure: 0.0472 mmHg at 25°C; (19)Exact Mass: 115.063329; (20)MonoIsotopic Mass: 115.063329; (21)Topological Polar Surface Area: 29.5; (22)Heavy Atom Count: 8; (23)Complexity: 78.5.

Preparation of 4-Formylmorpholine: It can be obtained by morpholine and formaldehyde. This reaction needs reagent KI and solvent water at ambient temperature. The yield is 83%.

Uses of 4-Formylmorpholine: It is used in the desulfurization of natural gas, synthetic gas, flue gas and gasoline. And it is the most widely used aromatic recovery solvent. Additionally, this chemical can react with benzothiazol-2-ylamine to get benzothiazol-2-yl-morpholin-4-ylmethylene-amine. This reaction needs reagent benzenesulfonyl chloride and solvent pyridine. The yield is 97 %. 

   

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. so people should not breathe vapour and avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure.
1. SMILES:O=CN1CCOCC1
2. InChI:InChI=1/C5H9NO2/c7-5-6-1-3-8-4-2-6/h5H,1-4H2
3. InChIKey:LCEDQNDDFOCWGG-UHFFFAOYAJ

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 16mL/kg (16mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat LD50 oral 6500uL/kg (6.5mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.

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