110-76-9

Basic information

• Product Name: 2-Ethoxyethylamine
• Synonyms: 2-ETHOXYETHYLAMINE 99+%;1-amino-2-ethoxyethane;2-Aminoethyl Ethyl Ether O-Ethylethanolamine;(2-ethoxyethyl)amine oxalate;2-ETHOXYETHYLAMINE;2-ETHOXY-1-ETHANAMINE;2-AMINOETHYL ETHYL ETHER;O-ETHYLETHANOLAMINE
• CAS NO: 110-76-9
• Molecular Formula: C₄H₁₁NO
• Molecular Weight: 89.14
• EINECS: 203-801-5
• Mol File: 110-76-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 105°C
• Flash Point: 17.7 °C
• Appearance: /
• Density: 0,85 g/cm3
• Vapor Pressure: 25.5mmHg at 25°C
• Refractive Index: 1.4080 to 1.4110
• PKA: pK1:6.26(+1) (25°C)
• Water Solubility: Completely miscible in water
• CAS DataBase Reference: 2-Ethoxyethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxyethylamine(110-76-9)
• EPA Substance Registry System: 2-Ethoxyethylamine(110-76-9)

Safety Data

• Hazard Codes: Xn
• Statements: 10-34-41-37/38-22
• Safety Statements: 26-36/37/39-39
• RIDADR: 2734
• HazardClass: 3/8
• PackingGroup: II
• Hazardous Substances Data: 110-76-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow transparent liquid

InChI:InChI=1/C4H11NO/c1-2-6-4-3-5/h2-5H2,1H3/p+1

Synthetic route

2-ethoxy-ethanol (110-80-5) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
With copper chromite; ammonia at 200℃;
With phosphoric acid; pumice stone; ammonia at 200 - 240℃;
With ammonia; nickel at 200℃;

2-ethoxyacetonitrile (62957-60-2) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
With nickel Hydrogenation;

1-ethoxy-2-nitroethane (31890-52-5) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
With ethanol; platinum at 20℃; under 73550.8 Torr; Hydrogenation;
With nickel under 77228.3 Torr; Hydrogenation;

sodium ethanolate (141-52-6) + 2-bromoethylamine hydrobromide (2576-47-8) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
at 150 - 160℃;

chloroethylamine (689-98-5) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
With ethanol

ethyleneimine (151-56-4) + ethanol (64-17-5) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
(i) BF3-Et2O, (ii) /BRN= 1718733/, (iii) KOH; Multistep reaction;

Butyl-N-β-Ethoxyethylacetimidate (72821-42-2) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
With sulfuric acid

ethyl iodide (75-03-6) + ethanolamine (141-43-5) → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
(i) Na, (ii) /BRN= 505934/; Multistep reaction;

ethanol (64-17-5) + aziridinium picrate → 2-ethoxy-1-ethanamine (110-76-9)

sodium ethanolate (141-52-6) + hydrochloride of β-chloro-ethylamine → 2-ethoxy-1-ethanamine (110-76-9)

Conditions	Yield
at 150 - 160℃;

ethanol (64-17-5) + N-nitroso-ethylenediamine-N-sulfonic acid → 2-ethoxy-1-ethanamine (110-76-9)

phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-pyridin-2-yl)carbamate (670252-61-6) + 2-ethoxy-1-ethanamine (110-76-9) → N1-ethyl-5-(2-(((2-ethoxyethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20℃; for 1h;	100%

2-ethoxy-1-ethanamine (110-76-9) + C53H63N5O12 → C57H72N6O12

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 20℃; for 1.5h;	100%

2-ethoxy-1-ethanamine (110-76-9) + C57H73N7O12 → C61H82N8O12

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 20℃; for 1.5h;	100%

2-ethoxy-1-ethanamine (110-76-9) + benzotriazole-1-carbothioic acid ((R)-1-phenylethyl)amide (690634-09-4) → 1-(2-ethoxyethyl)-3-[(R)-1-phenylethyl]thiourea

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	99%

2-ethoxy-1-ethanamine (110-76-9) + 2-(2-oxo-2-phenylethyl)-2,3-dihydro-1H-inden-1-one (89506-40-1) → 1-(2-ethoxyethyl)-2-phenyl-1,4-dihydroindeno[1,2-b]pyrrole (1325642-75-8)

Conditions	Yield
With bismuth (III) nitrate pentahydrate In tetrahydrofuran at 100℃; for 18h; Paal-Knorr pyrrole synthesis;	99%

2-ethoxy-1-ethanamine (110-76-9) + 1,3-dibromo-6,7-dihydro-4H-pyrazino[2,1-a]isoquinolin-4-one (1620230-93-4) → 1-bromo-3-(2-ethoxyethylamino)-6,7-dihydro-4H-pyrazino[2,1-a]isoquinolin-4-one (1620231-06-2)

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	99%

2-ethoxy-1-ethanamine (110-76-9) + 2-Oxo-2H-furo<2,3-h>-1-benzopyran-3-carbonyl chloride (172375-50-7) → 2-Oxo-2H-furo[2,3-h]chromene-3-carboxylic acid (2-ethoxy-ethyl)-amide

Conditions	Yield
In tetrahydrofuran for 24h; Ambient temperature;	98%

2-ethoxy-1-ethanamine (110-76-9) + 4-iodobenzenesulfonyl chloride (98-61-3) → N-(2-ethoxyethyl)-4-iodobenzenesulphonamide (600638-57-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 18h;	98%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 18h;	98%

2-ethoxy-1-ethanamine (110-76-9) + 2,4-Difluoronitrobenzene (446-35-5) → N-(2-ethoxyethyl)-5-fluoro-2-nitroaniline (1233231-52-1)

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 20℃;	98%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	499 mg

2-ethoxy-1-ethanamine (110-76-9) + acetylacetone (123-54-6) → 4-((2-ethoxyethyl)amino)pent-3-en-2-one

Conditions	Yield
In diethyl ether for 1h; Inert atmosphere; Schlenk technique; Reflux;	98%
In diethyl ether

2-ethoxy-1-ethanamine (110-76-9) + cis-3-(9-benzyl-2,3,4,4a,9,9a-hexahydro-1H-carbazol-4a-yl)-propanoic acid → cis-3-(9-benzyl-2,3,4,4a,9,9a-hexahydro-1H-carbazol-4a-yl)-N-(2-ethoxyethyl)propanamide

Conditions	Yield
Stage #1: cis-3-(9-benzyl-2,3,4,4a,9,9a-hexahydro-1H-carbazol-4a-yl)-propanoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 23℃; for 1h; Stage #2: 2-ethoxy-1-ethanamine In dichloromethane at 23℃; for 1h;	98%

2-ethoxy-1-ethanamine (110-76-9) + acetylacetone (123-54-6) → N-(2′-ethoxyethyl)-2-penten-2-ol-4-imine

Conditions	Yield
Stage #1: 2-ethoxy-1-ethanamine; acetylacetone In diethyl ether for 1h; Reflux; Stage #2: In diethyl ether at 20℃;	95.7%

2-Chloro-3-nitropyridine (5470-18-8) + 2-ethoxy-1-ethanamine (110-76-9) → N-(2-ethoxyethyl)-3-nitro-2-pyridinamine (118705-43-4)

Conditions	Yield
at 80℃; for 0.166667h;	95%
With sodium bicarbonate In ethanol	25.5 parts (100%)
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 0.75h;	567 mg

2-ethoxy-1-ethanamine (110-76-9) + phenyl isopropyl ketone (611-70-1) → N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl)-propylideneamine (139007-06-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	95%

2-ethoxy-1-ethanamine (110-76-9) + C21H35ClN6O6 (1588764-64-0) → C25H45N7O7 (1588764-68-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 140℃; for 1.5h; Microwave irradiation;	95%

2-ethoxy-1-ethanamine (110-76-9) + N-(2-benzoylphenyl)-2,2,2-trichloroacetamide (35382-88-8) → 3-(4-ethoxyethyl)-4-phenyl-4-(trichloromethyl)-3,4-dihydroquinazolin-2(1H)-one (853942-71-9)

Conditions	Yield
In dimethyl sulfoxide at 20℃;	94%
In dimethyl sulfoxide

carbon disulfide (75-15-0) + 2-ethoxy-1-ethanamine (110-76-9) + ethyl Bromopyruvate (70-23-5) → ethyl 3-(ethoxyethyl)-4-hydroxy-2-thioxothiazolidine-4-carboxylate

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In neat (no solvent) at 20℃; for 2.5h; Green chemistry;	94%

2-ethoxy-1-ethanamine (110-76-9) + C10H12Cl2N4O2 (1588764-72-0) → C14H22ClN5O3 (1588764-76-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h;	93%

2-ethoxy-1-ethanamine (110-76-9) + 3-(3-amino-6-chloropyridazin-4-yl)phenol → 3-(3-amino-6-((2-ethoxyethyl)amino)pyridazin-4-yl)phenol

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 60℃; for 0.416667h; Buchwald-Hartwig Coupling; Inert atmosphere;	93%

2-[2-(vinyloxy)ethoxymethyl]oxirane (16801-19-7) + 2-ethoxy-1-ethanamine (110-76-9) → 1-(2-vinyloxyethoxy)-3-(2-ethoxyethylamino)propan-2-ol (271776-66-0)

Conditions	Yield
In water at 50℃; for 8h; Addition;	91.7%
at 50 - 60℃; for 8h;	69.7%

3-O-benzylmaltol (61049-69-2) + 2-ethoxy-1-ethanamine (110-76-9) → 1-(2'-ethoxyethyl)-2-methyl-3-benzyloxy-4-(1H)-pyridinone

Conditions	Yield
In ethanol at 80℃; for 5h; Inert atmosphere; Microwave irradiation;	91%

2-ethoxy-1-ethanamine (110-76-9) + 6,7-diamino-1H,3H-benzo[de]isochromene-1,3-dione (5589-17-3) → C16H17N3O3

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 3h; Temperature; Inert atmosphere;	91%

2-ethoxy-1-ethanamine (110-76-9) + (3-phenylamino-4,5-dihydro-benzo[g]indazol-2-yl)-acetic acid ethyl ester (301644-15-5) → N-(2-ethoxy-ethyl)-2-(3-phenylamino-4,5-dihydro-benzo[g]indazol-2-yl)-acetamide

Conditions	Yield
at 100℃; for 4h; Acylation;	90%

2-ethoxy-1-ethanamine (110-76-9) + 4-bromobenzenesulfonyl chloride (98-58-8) → 4-bromo-N-(2-ethoxyethyl)benzenesulfonamide (321710-87-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 0.166667h;	90%

5-(2,7-dichloro-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methylpyrimidine-2,4(1H,3H)-dione + 2-ethoxy-1-ethanamine (110-76-9) → 5-(7-chloro-2-((2-ethoxyethyl)amino)-4H-benzo[5,6]cyclohepta-[1,2-d]thiazol-4-yl)-1-methylpyrimidine-2,4(1H,3H)-dione

Conditions	Yield
With triethylamine In 1,4-dioxane Inert atmosphere;	90%

2,6-dicholoro-3-nitropyridine (16013-85-7) + 2-ethoxy-1-ethanamine (110-76-9) → (6-chloro-3-nitro-pyridin-2-yl)-(2-ethoxy-ethyl)-amine (926910-32-9)

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 50℃; for 6h;	89%
With sodium carbonate In isopropyl alcohol at 0 - 20℃;
With sodium carbonate In isopropyl alcohol at 0 - 20℃; for 17h;

2-ethoxy-1-ethanamine (110-76-9) + 6-chloro-4-(4-(trifluoromethyl)phenyl)pyridazin-3-amine → N3-(2-ethoxyethyl)-5-(4-(trifluoromethyl)phenyl)pyridazine-3,6-diamine

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 60℃; for 0.416667h; Buchwald-Hartwig Coupling; Inert atmosphere;	88%

1 ,6-dibromohexane (629-03-8) + 2-ethoxy-1-ethanamine (110-76-9) → N,N'-bis-(2-ethoxy-ethyl)-hexanediyldiamine (740043-68-9)

Conditions	Yield
In neat (no solvent) at 40 - 60℃;	87%
With water
With water

2-ethoxy-1-ethanamine (110-76-9) + Phthaloyl dichloride (88-95-9) → 3-[(E)-2-Ethoxy-ethylimino]-3H-isobenzofuran-1-one (113336-86-0)

Conditions	Yield
With triethylamine In benzene	87%

2-ethoxy-1-ethanamine (110-76-9) + 3-bromo-1-ethoxy-6,7-dihydro-4H-pyrazino[2,1-a]isoquinolin-4-one (1620230-92-3) → 1-ethoxy-3-(2-ethoxyethylamino)-6,7-dihydro-4H-pyrazino[2,1-a]isoquinolin-4-one (1620231-00-6)

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	87%

Upstream product

• 151-56-4 ethyleneimine 
• 64-17-5 ethanol 
• 72821-42-2 Butyl-N-β-Ethoxyethylacetimidate 
• 75-03-6 ethyl iodide 
• 141-43-5 ethanolamine 
• 141-52-6 sodium ethanolate 
• 689-98-5 chloroethylamine 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 31890-52-5 1-nitro-2-ethoxyethane 
• 110-80-5 2-ethoxy-ethanol 
• 62957-60-2 2-ethoxyacetonitrile 

Downstream Products

• 93144-07-1 N,N'-bis(2-ethoxyethyl)-p-xylene-α,α'-diamine 
• 144454-98-8 2-[5-(3,5-Diphenyl-pyrazol-1-yl)-4-phenyl-pyrimidin-2-ylamino]-N-(2-ethoxy-ethyl)-acetamide 
• 144455-04-9 2-{[5-(3,5-Diphenyl-pyrazol-1-yl)-4-phenyl-pyrimidin-2-yl]-methyl-amino}-N-(2-ethoxy-ethyl)-acetamide 
• 113112-80-4 N-(2-Ethoxy-ethyl)-N'-(5-o-tolyl-[1,3,4]thiadiazol-2-yl)-guanidine; hydrochloride 
• 72106-69-5 N-benzylidene-2-ethoxyethylamine 
• 95893-88-2 N-(β-ethoxyethyl)-o-nitroaniline 
• 214919-18-3 N-(2-ethoxyethyl)-P,P,P',P'-tetrabenzylimidodiphosphate 
• 301644-19-9 N-(2-ethoxy-ethyl)-2-(3-phenylamino-4,5-dihydro-benzo[g]indazol-2-yl)-acetamide 
• 301644-23-5 2-[3-(4-chloro-phenylamino)-4,5-dihydro-benzo[g]indazol-2-yl]-N-(2-ethoxy-ethyl)-acetamide 
• 301644-26-8 2-[3-(4-bromo-phenylamino)-4,5-dihydro-benzo[g]indazol-2-yl]-N-(2-ethoxy-ethyl)-acetamide 
• 38256-94-9 N-methyl-N-(2-ethoxyethyl)amine 
• 26311-17-1 [N₁₁,2O₂] 
• 853942-71-9 3-(4-ethoxyethyl)-4-phenyl-4-(trichloromethyl)-3,4-dihydroquinazolin-2(1H)-one 

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Studies on the mechanism of ethanolamine ammonia lyase using 2-Ethoxyethylamine (cas 110-76-9) as a substrate08/20/2019

In addition to ethanolamine and propanolamine it was found that 2-ethoxyethylamine is a substrate for the corrin-dependent enzyme ethanolamine-ammonia lyase. The enzyme has the same V for 2-ethoxyethylamine as ethanolamine, but the Km for this substrate is 4.3 · 10−3 M. Acetaldehyde and ethylam...detailed

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