Conditions | Yield |
---|---|
With triphenylphosphine; ruthenium trichloride at 120℃; for 2h; | 100% |
Conditions | Yield |
---|---|
at 80℃; for 72h; | 85% |
With potassium carbonate In acetonitrile for 3h; Reflux; | 83% |
With potassium carbonate In acetonitrile for 3h; Reflux; | 83% |
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 48h; Heating; | 83% |
at 90 - 170℃; | |
With potassium carbonate at 120℃; | |
With ethanol; copper |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0 - 50℃; for 8h; | 76.6% |
Conditions | Yield |
---|---|
With sodium hydroxide at 40 - 45℃; | 67% |
With acetone | |
With benzene |
Conditions | Yield |
---|---|
With water at 0℃; | |
With methanol |
Conditions | Yield |
---|---|
With sulfuric acid at 160 - 170℃; | |
With cation exchanger at 160 - 220℃; | |
With sulfuric acid at 130 - 150℃; for 15h; |
triethanolamine hydrochloride
A
morpholine
B
2-(morpholin-4-yl)ethanol
C
1,2-dimorpholylethane
D
2,2'-dimorpholinodiethyl ether
Conditions | Yield |
---|---|
at 190 - 230℃; |
Conditions | Yield |
---|---|
at 200 - 205℃; under 40 Torr; anschliessend Erhitzen mit wss.-aethanol. KOH; | |
at 200 - 205℃; under 40 Torr; | |
at 280℃; under 7 Torr; anschliessend Erhitzen mit wss.-aethanol. KOH; |
Conditions | Yield |
---|---|
With ammonium hydroxide at 65 - 80℃; under 2206.5 - 3677.5 Torr; anschliessend Behandeln mit wss. NaOH; |
morpholine
ethylene glycol
A
2-(morpholin-4-yl)ethanol
B
1,2-dimorpholylethane
Conditions | Yield |
---|---|
With triphenylphosphine; ruthenium trichloride at 120℃; for 2h; Product distribution; other catalyst, also with THF, other phosphine, also at 220 degC; | |
With hydridochlorotris(triphenylphosphine)ruthenium(II) at 100℃; for 5.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With ruthenium trichloride at 120℃; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With Ru(CO)12; triphenylphosphine In tetrahydrofuran at 220℃; for 15h; Yield given; | |
With tris(triphenylphosphine)ruthenium(II) chloride at 100℃; for 2h; Product distribution; Mechanism; other diol; other secondary amines; other catalysts; var. temp. and reaction times; |
methyl 2-morpholin-4-ylacetate
2-(morpholin-4-yl)ethanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Heating; |
phenyl-carbamic acid-(2-morpholino-ethyl ester); hydrochloride
A
2-(morpholin-4-yl)ethanol
B
carbon dioxide
C
aniline
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 40℃; Rate constant; Thermodynamic data; var. temp., EA; |
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In ethanol for 12h; Reflux; |
triethanolamine
ethanolamine
A
2-(morpholin-4-yl)ethanol
B
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With oxygen; zirconium(IV) oxide In water at 325℃; under 760.051 Torr; Product distribution / selectivity; |
1,2-dimorpholinoethane-1,2-dione
A
2-(morpholin-4-yl)ethanol
B
2-hydroxy-1-(morpholin-4-yl)ethan-1-one
C
ethylene glycol
Conditions | Yield |
---|---|
With hydrogen; Cu/Al2O3/SiO2 In methanol at 170℃; under 41254.1 Torr; for 16.5h; Autoclave; |
triethanolamine
A
2-(morpholin-4-yl)ethanol
B
2,2'-dimorpholinodiethyl ether
Conditions | Yield |
---|---|
With sulfuric acid at 130 - 200℃; for 15h; Temperature; Time; |
2-(morpholin-4-yl)ethanol
N-(2-bromoethyl)morpholine
Conditions | Yield |
---|---|
With dibromotriphenylphosphorane In dichloromethane at 0 - 20℃; | 100% |
With phosphorus tribromide In dichloromethane at 0 - 45℃; | 23.7% |
With hydrogen bromide at 130℃; |
2-(morpholin-4-yl)ethanol
4-(2-hydroxyethyl)morpholine 4-oxide
Conditions | Yield |
---|---|
With dihydrogen peroxide | 100% |
2-(morpholin-4-yl)ethanol
4-fluoro-2-methoxy-1-nitrobenzene
4-(2-(3-methoxy-4-nitrophenoxy)ethyl)morpholine
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In water; toluene at 18 - 60℃; for 22h; | 100% |
With tetrabutylammomium bromide; water; potassium hydroxide In toluene at 60℃; for 18h; | 98% |
With benzyltriethylammonium bromide; potassium hydroxide In water; toluene at 60℃; for 24h; | 42.4% |
With tetrabutyl-ammonium chloride; potassium hydroxide In toluene at 60℃; for 24h; | 42% |
2-(morpholin-4-yl)ethanol
4-bromo-phenol
1-bromo-4-(2-morpholinoethoxy)benzene
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 110℃; for 17h; Mitsunobu Displacement; Inert atmosphere; | 100% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2.16667h; |
2-(morpholin-4-yl)ethanol
ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate
1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-ethoxycarbonyl-4-(2-morpholinoethoxy)-1H-pyrazole
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; | 100% |
2-(morpholin-4-yl)ethanol
3-chlorosulfonyl-4-chlorobenzoyl chloride
2-(morpholin-4-yl)ethyl 4-chloro-3-chlorosulfonylbenzoate
Conditions | Yield |
---|---|
In dichloromethane for 12h; | 100% |
2-(morpholin-4-yl)ethanol
2-morpholin-4-yl-potassium ethoxide
Conditions | Yield |
---|---|
With potassium In ethanol at 0℃; Product distribution / selectivity; | 100% |
2-(morpholin-4-yl)ethanol
Conditions | Yield |
---|---|
With sodium at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Stage #2: 1,2-dichloro-4-fluoro-5-nitrobenzene In tetrahydrofuran; mineral oil at 0℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate at 110℃; for 0.5h; Microwave irradiation; | 100% |
2-(morpholin-4-yl)ethanol
4-benzyloxy-2-fluoro-1-nitrobenzene
Conditions | Yield |
---|---|
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20 - 30℃; for 1h; Stage #2: 4-benzyloxy-2-fluoro-1-nitrobenzene In tetrahydrofuran; mineral oil at 20℃; for 1h; | 99.2% |
2-(morpholin-4-yl)ethanol
Conditions | Yield |
---|---|
99% |
2-(morpholin-4-yl)ethanol
6-(2-morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid isopropyl amide
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; benzene at 0 - 20℃; for 2h; | 99% |
Conditions | Yield |
---|---|
In toluene for 120h; Reflux; | 98% |
2-(morpholin-4-yl)ethanol
6-chloropyridine-3-ol
4-(2-((6-chloropyridin-3-yl)oxy)ethyl)morpholine
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4h; | 97% |
2-(morpholin-4-yl)ethanol
1-bromomethyl-4-iodobenzene
Conditions | Yield |
---|---|
at 72℃; for 18h; | 97% |
In N,N-dimethyl-formamide at 72℃; Inert atmosphere; | 97% |
2-(morpholin-4-yl)ethanol
1,3-Benzothiazole
2-amino-6-hydroxybenzothiazole
diethylazodicarboxylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; triphenylphosphine In tetrahydrofuran; ethyl acetate | 96% |
With sodium hydrogencarbonate; triphenylphosphine In tetrahydrofuran; ethyl acetate | 96% |
With sodium hydrogencarbonate; triphenylphosphine In tetrahydrofuran; ethyl acetate | 96% |
2-(morpholin-4-yl)ethanol
2-Fluoro-5-nitrobenzotrifluoride
4-[2-(4-nitro-2-trifluoromethyl-phenoxy)-ethyl]-morpholine
Conditions | Yield |
---|---|
Stage #1: 2-(morpholin-4-yl)ethanol With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-Fluoro-5-nitrobenzotrifluoride In tetrahydrofuran at 20℃; for 4h; | 96% |
2-(morpholin-4-yl)ethanol
8,8′,8″-(hydroxymethanetriyl)tris[2,2,6,6-tetramethylbenzo[1,2-d:4,5-d′]bis([1,3]dithiole)-4-carboxylic acid]
tris(2,2,6,6-tetramethyl-8-{[2-(morpholin-4-yl)ethyl]carbonyl}-benzo[1,2-d;4,5-d']bis[1,3]dithiol-4-yl)methanol
Conditions | Yield |
---|---|
Stage #1: tris(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d']bis[1,3]dithiol-4-yl)methanol With 1,1'-carbonyldiimidazole In tetrahydrofuran at 55℃; for 4h; Inert atmosphere; Stage #2: 2-(morpholin-4-yl)ethanol In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #3: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 24h; Inert atmosphere; | 96% |
2-(morpholin-4-yl)ethanol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h; | 96% |
2-(morpholin-4-yl)ethanol
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h; Mitsunobu reaction; | 95% |
2-(morpholin-4-yl)ethanol
3-hydroxy-4-methoxybenzoate
A
4-Methoxy-3-(2-morpholin-4-yl-ethoxy)benzoic acid methyl ester
B
diethyl hydrazodicarboxylate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In ethyl acetate | A 95% B n/a |
2-(morpholin-4-yl)ethanol
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; | 95% |
2-(morpholin-4-yl)ethanol
methyl p-toluene sulfonate
S4-(2-hydroxyethyl)-4-methylmorpholin-4-ium 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
In acetonitrile for 4h; Reflux; | 94.4% |
In acetonitrile for 4h; Reflux; | 87% |
In acetonitrile for 4h; Reflux; | 84% |
2-(morpholin-4-yl)ethanol
3-chloro-isonicotinonitrile
Conditions | Yield |
---|---|
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: 3-chloro-isonicotinonitrile In tetrahydrofuran; mineral oil at 20℃; for 18h; | 94% |
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: 3-chloro-isonicotinonitrile In tetrahydrofuran; mineral oil at 20℃; for 18h; | 94% |
2-(morpholin-4-yl)ethanol
1-oxo-6-hydroxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester
6-(2-morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; benzene at 0 - 20℃; for 2h; | 93% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; benzene at 0 - 20℃; for 2h; | 93% |
2-(morpholin-4-yl)ethanol
4-(4-nitro-3-(prop-2-ynyloxy)phenoxyethyl)morpholine
Conditions | Yield |
---|---|
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 4-fluoro-1-nitro-2-(prop-2-yn-1-yloxy)benzene In N,N-dimethyl-formamide at -35℃; for 6h; Inert atmosphere; | 93% |
2-(morpholin-4-yl)ethanol
4-Iodophenol
4-<2-(p-iodophenoxy)ethyl>morpholine
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 17h; Cooling with ice; | 93% |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In ethyl acetate | 92% |
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran | |
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran |
IUPAC Name: 2-Morpholin-4-ylethanol
Molecular Formula: C6H13NO2
Molecular Weight: 131.17 g/mol
Molecular structure of 4-Morpholineethanol (CAS NO.622-40-2):
EINECS: 210-734-5
Melting Point: -1 °C
Boiling Point: 227 °C at 757 mm Hg(lit.)
Density: 1.083 g/mL at 25 °C(lit.)
Refractive Index: n20/D 1.476(lit.)
Flash Point: 211 °F
Water Solubility: miscible
Molar Refractivity: 34.48 cm3
Molar Volume: 123.6 cm3
XLogP3-AA: -0.8
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Exact Mass: 131.094629
MonoIsotopic Mass: 131.094629
Topological Polar Surface Area: 32.7
Heavy Atom Count: 9
Canonical SMILES: C1COCCN1CCO
InChI: InChI=1S/C6H13NO2/c8-4-1-7-2-5-9-6-3-7/h8H,1-6H2
InChIKey: KKFDCBRMNNSAAW-UHFFFAOYSA-N
Classification Code: Mutation data; Skin / Eye Irritant
4-Morpholineethanol (CAS NO.622-40-2) is commonly used in organic synthesis. It is also a kind of very important chemical pharmaceutical intermediates.
1. | skn-rbt 10 mg/24H open | JIHTAB Journal of Industrial Hygiene and Toxicology. 30 (1948),63. | ||
2. | eye-rbt 20 mg SEV | AJOPAA American Journal of Ophthalmology. 29 (1946),1363. | ||
3. | dns-rat:lvr 5 g/L | MUREAV Mutation Research. 136 (1984),153. | ||
4. | orl-rat LD50:5500 mg/kg | JACTDZ Journal of the American College of Toxicology. 1 (1990),16. | ||
5. | ipr-mus LD50:3600 mg/kg | CANCAR Cancer. 2 (1949),1055. | ||
6. | scu-mus LD50:2650 mg/kg | AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 109 (1957),108. | ||
7. | par-mus LDLo:4800 mg/kg | CBCCT* “Summary Tables of Biological Tests” National Research Council Chemical-Biological Coordination Center. 7 (1955),691. | ||
8. | skn-gpg LD50:2500 mg/kg | JIHTAB Journal of Industrial Hygiene and Toxicology. 30 (1948),63. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi
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:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
RTECS: QE3510000
F: 10-23
HS Code: 29349990
Moderately toxic by skin contact, subcutaneous, and intraperitoneal routes. Mildly toxic by ingestion and parenteral routes. Mutation data reported. A skin and severe eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.
4-Morpholineethanol (CAS NO.622-40-2) is also named as 2-(4-Morpholinyl)ethanol ; 2-Morpholinoethanol ; 4-(2-Hydroxyethyl)morpholine ; 4-27-00-00056 (Beilstein Handbook Reference) ; AI3-03872 ; BRN 0104375 ; Ethanol, 2-(morpholinyl)- ; Ethanol, 2-morpholino- ; Hydroxyethylmorpholine ; Morpholine ethanol ; Morpholineethanol ; N-(2-Hydroxyethyl)morfolin ; N-(2-Hydroxyethyl)morfolin [Czech] ; N-(2-Hydroxyethyl)morpholine ; N-beta-Hydroxyethylmorpholine ; NSC 1946 ; beta-Morpholinoethanol ; beta-Oxyaethyl-morpholin ; beta-Oxyaethyl-morpholin [German] ; beta-Oxyaethyl-morpholin [German] . 4-Morpholineethanol (CAS NO.622-40-2) is clear colourless to yellow liquid.
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