6281-42-1

Basic information

• Product Name: 1-(2-Aminoethyl)imidazolidin-2-one
• Synonyms: BUTTPARK 52\06-90;CHEMBRDG-BB 4005390;1-(2-AMINOETHYL)IMIDAZOLIDIN-2-ONE;1-(2-AMINOETHYL)-2-IMIDAZOLIDINONE;1-(2-AMINOETHYL)-2-IMIDAZOLIDONE;1-(BETA-AMINOETHYL)-2-IMIDAZOLIDONE;1-(2-aminoethyl)-2-imidazolidinon;1-(2-aminoethyl)-2-imidazolone
• CAS NO: 6281-42-1
• Molecular Formula: C₅H₁₁N₃O
• Molecular Weight: 129.16
• EINECS: 228-491-9
• Product Categories: Imidazoles & Benzimidazoles;Imidazoles & Benzimidazoles
• Mol File: 6281-42-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 138-140/0.11mm
• Flash Point: 173.4 °C
• Appearance: /
• Density: 1.137 g/cm³
• Vapor Pressure: 1.85E-05mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 14.42±0.20(Predicted)
• CAS DataBase Reference: 1-(2-Aminoethyl)imidazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Aminoethyl)imidazolidin-2-one(6281-42-1)
• EPA Substance Registry System: 1-(2-Aminoethyl)imidazolidin-2-one(6281-42-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 22-26-36/37/39-45
• RIDADR: 3259
• Hazardous Substances Data: 6281-42-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to off-white liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C5H11N3O/c6-1-3-8-4-2-7-5(8)9/h1-4,6H2,(H,7,9)

Synthetic route

1,5-diamino-3-azapentane (111-40-0) + urea (57-13-6) → 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
With ammonia at 125 - 160℃; Concentration; Temperature; Inert atmosphere; Large scale;	96%
at 210℃;
at 130 - 210℃; for 3h;

carbon dioxide (124-38-9) + 1,5-diamino-3-azapentane (111-40-0) → 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
With cerium(IV) oxide In ethanol at 160℃; for 8h;	36%
With ethanolamine at 190℃; for 0.5h; Catalytic behavior; Reagent/catalyst;

1,3,6-triazabicyclo[3.3.0]oct-4-ene (6573-15-5) → 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
With water

1-(2-chloroethyl)imidazolidin-2-one (2387-20-4) → 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
With ammonium hydroxide at 100℃;

1-(2-aminoethyl)-2-imidazolidinethione (40778-59-4) → 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
With ammonium hydroxide; dihydrogen peroxide
Multi-step reaction with 2 steps 1: chloroacetic acid 2: H2O View Scheme

1-(2-chloroethyl)imidazolidin-2-one (2387-20-4) + ammonium hydroxide → 2-(2-amino-4,5-dihydro-imidazol-1-yl)-ethanol (98137-74-7) + 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
at 100℃;

1,5-diamino-3-azapentane (111-40-0) → 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
With urea

bis-(2-phenylacetylamino-ethyl)-carbamic acid 4-nitro-phenyl ester (757967-03-6) → phenylacetic acid (103-82-2) + 2-aminoethylimidazolidone (6281-42-1) + 4-nitro-phenol (100-02-7) + (4-hydroxyphenyl)methanol (623-05-2) + carbon dioxide (124-38-9)

Conditions	Yield
With water; penicillin-G-amidase In Chremephor EL; dimethyl sulfoxide at 37℃; pH=7.4; Kinetics; Enzymatic reaction; Aqueous phosphate buffer;

1,5-diamino-3-azapentane (111-40-0) + carbonic acid dimethyl ester (616-38-6) → 2-aminoethylimidazolidone (6281-42-1)

Conditions	Yield
With sodium methylate In methanol at 23 - 120℃; for 4h; Inert atmosphere;
With sodium methylate In methanol at 23 - 120℃; for 4h; Concentration; Solvent; Inert atmosphere;

2-oxo-imidazolidine-1-ethanol (3699-54-5) + 1,5-diamino-3-azapentane (111-40-0) → 2-aminoethylimidazolidone (6281-42-1) + 2-(2-Aminoethylamino)ethanol (111-41-1)

Conditions	Yield
at 270℃; for 5h; Autoclave; Inert atmosphere;	A 30.5 %Chromat. B 16.8 %Chromat.

imidazolidone (120-93-4) + ethylenediamine (107-15-3) → 2-aminoethylimidazolidone (6281-42-1) + N,N'-diethylurea (623-76-7) + U2TETA (166532-70-3) + 1,1'-(1,2-ethanediyl)di(2-imidazolidinone) (24368-15-8) + U1TETA + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With dimethylenecyclourethane at 260℃; for 1.5h; Inert atmosphere;

...Expand

imidazolidone (120-93-4) + ethylenediamine (107-15-3) → 2-aminoethylimidazolidone (6281-42-1) + U2TETA (166532-70-3) + 1,1'-(1,2-ethanediyl)di(2-imidazolidinone) (24368-15-8) + U1TETA + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With dimethylenecyclourethane at 250℃; for 5.5h; Microwave irradiation; Inert atmosphere;

dimethylenecyclourethane (497-25-6) + imidazolidone (120-93-4) + ethylenediamine (107-15-3) → 2-oxo-imidazolidine-1-ethanol (3699-54-5) + 2-aminoethylimidazolidone (6281-42-1) + U2TETA (166532-70-3) + 1,1'-(1,2-ethanediyl)di(2-imidazolidinone) (24368-15-8) + U1TETA + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
at 250℃; for 5.5h; Inert atmosphere;

...Expand

dimethylenecyclourethane (497-25-6) + imidazolidone (120-93-4) + ethylenediamine (107-15-3) → 2-oxo-imidazolidine-1-ethanol (3699-54-5) + 2-aminoethylimidazolidone (6281-42-1) + 2-(2-Aminoethylamino)ethanol (111-41-1) + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
at 260℃; for 3h;

imidazolidone (120-93-4) + ethanolamine (141-43-5) + ethylenediamine (107-15-3) → 2-aminoethylimidazolidone (6281-42-1) + U2TETA (166532-70-3) + 1,1'-(1,2-ethanediyl)di(2-imidazolidinone) (24368-15-8) + U1TETA + 1,5-diamino-3-azapentane (111-40-0) + triethylentetramine (112-24-3)

Conditions	Yield
With dimethylenecyclourethane at 250℃; for 5h; Inert atmosphere;

...Expand

2-aminoethylimidazolidone (6281-42-1) + 11-mercaptounadecanoic acid (71310-21-9) → 11-mercapto-N-[2-(2-oxoimidazolidin-1-yl)ethyl]undecaneamide

Conditions	Yield
at 160℃; for 6h; Inert atmosphere;	100%

2-aminoethylimidazolidone (6281-42-1) + 1-(5-(methoxycarbonyl)-4-{[2-(trifluoromethyl)benzyl]oxy}thien-2-yl)-1H-benzimidazole-5-carboxylic acid (660870-46-2) → methyl 5-[5-({[2-(2-oxoimidazolidin-1-yl)ethyl]amino}carbonyl)-1H-benzimidazol-1-yl]-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) for 2h;	95%

2-aminoethylimidazolidone (6281-42-1) + 5-(4-chlorophenyl)-2-{[1-(4-chloropyridin-3-yl)-1H-1,2,4-triazol-3-yl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one → 5-(4-chlorophenyl)-2-{[1-(4-{[2-(2-oxoimidazolidin-1-yl)ethyl]amino}pyridin-3-yl)-1H-1,2,4-triazol-3-yl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions	Yield
In ethanol Reflux;	94%

2-aminoethylimidazolidone (6281-42-1) + 2-chloro-4-[7-(2-chloro-pyridin-4-yl)-benzo[b]thiophen-2-yl]-pyrimidine (1034658-89-3) → 1-(2-{4-[7-(2-chloro-pyridin-4-yl)-benzo[b]thiophen-2-yl]pyrimidin-2-ylamino}ethyl)imidazolidin-2-one (1034657-98-1)

Conditions	Yield
In butan-1-ol at 120℃; for 5h;	93%

2-aminoethylimidazolidone (6281-42-1) + 2,4-dicyano-1-butene (1572-52-7) → C11H17N5O

Conditions	Yield
In water at 75 - 80℃; Inert atmosphere;	89%

2-aminoethylimidazolidone (6281-42-1) + ethylene dibromide (106-93-4) → ,4,7-triazacyclononan-1,4-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 100℃; for 60h; Reagent/catalyst; Solvent; Temperature;	87.09%

2-aminoethylimidazolidone (6281-42-1) + dichlorobenzenesulfonyl chloride (82417-45-6) → 2,3-dichloro-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzenesulphonamide (886236-60-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	87%

Divinyl sulfone (77-77-0) + 2-aminoethylimidazolidone (6281-42-1) → 1-<2-N-(1,1-dioxidothiomorpholinoethyl)>-2-imidazolidinone (85694-70-8)

Conditions	Yield
In ethanol for 3h; Ambient temperature;	83%

2-aminoethylimidazolidone (6281-42-1) + m-isopropenyl-α,α-dimethylbenzyl carbamic acid methyl ester (90826-32-7) → m-TMU (137559-77-4)

Conditions	Yield
1,3-diacetoxy-1,1,3,3-tetrabutyldistannoxane at 140℃; under 30 Torr; for 3h;	83%

2-aminoethylimidazolidone (6281-42-1) + 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine (2946-89-6) → N-nitro-N'-[2-(2-oxo-imidazolidin-3-yl)ethyl]guanidine

Conditions	Yield
In methanol at 20℃;	80%

2-aminoethylimidazolidone (6281-42-1) + 4‐(3‐bromo‐4‐fluorophenyl)‐3‐(4‐nitro‐1,2,5‐oxadiazol‐3‐yl)‐4,5‐dihydro‐1,2,4‐oxadiazol‐5‐one → 4‐(3‐bromo‐4‐fluorophenyl)‐3‐(4‐{[2‐(2‐oxoimidazolidin‐1‐yl)ethyl]amino}‐1,2,5‐oxadiazol‐3‐yl)‐1,2,4‐oxadiazol‐5‐one

Conditions	Yield
In acetonitrile	78%

2-aminoethylimidazolidone (6281-42-1) + acrylic acid (79-10-7) → 3,3'-{[2-(2-oxoimidazolidin-1-yl)ethyl]imino}dipropanoic acid

Conditions	Yield
In isopropyl alcohol at 60℃; for 2h; Inert atmosphere;	75%

2-aminoethylimidazolidone (6281-42-1) + 2-(methylsulfonyl)-4-(5-(morpholinosulfonyl)thiophen-2-yl)pyrimidine (893441-65-1) → 1-(2-(4-(5-(morpholinosulfonyl)thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

Conditions	Yield
With triethylamine In toluene for 6h; Heating / reflux;	72%

2-aminoethylimidazolidone (6281-42-1) + C18H12FNO2 (1367126-25-7) → 1-(2-(((6-(4-(4-fluorophenoxy)phenyl)pyridin-2-yl)methyl)amino)ethyl)imidazolidin-2-one (1367124-97-7)

Conditions	Yield
Stage #1: 2-aminoethylimidazolidone; C18H12FNO2 In tetrahydrofuran at 20℃; for 14h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 0.333333h;	72%

2-aminoethylimidazolidone (6281-42-1) + C20H18FNO4S (1367126-49-5) → 1-(2-((2-(6-(4-(4-fluorophenoxy)phenyl)pyridin-2-yl)ethyl)amino)ethyl)imidazolidin-2-one (1367124-99-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 40℃; for 14h;	70%

2-aminoethylimidazolidone (6281-42-1) + 4-(5'-bromo-2'-thienyl)-2-chloropyrimidine (131022-68-9) → 1-(2-(4-(5-bromothiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

Conditions	Yield
With triethylamine In isopropyl alcohol for 30h; Heating / reflux;	68%

2-aminoethylimidazolidone (6281-42-1) + 3,4-dichlorophenylisocyanate (102-36-3) → C12H14Cl2N4O2

Conditions	Yield
With triethylamine In toluene at 5℃; for 24h;	68%

2-aminoethylimidazolidone (6281-42-1) + 4-chloro-3-formylcoumarin (50329-91-4) → C15H15N3O4

Conditions	Yield
With triethylamine In ethanol for 0.0833333h; Heating;	67%

2-aminoethylimidazolidone (6281-42-1) + C19H10(2)H3F3N2O2 → d-1-(2-(((6-(2-methyl-4-((5-(trifluoromethyl)pyridin-2-yl)oxy)-phenyl-3,5,6-d3)pyridin-2-yl)methyl)amino)ethyl)imidazolidin-2-one

Conditions	Yield
Stage #1: 2-aminoethylimidazolidone; C19H10(2)H3F3N2O2 In methanol at 20℃; for 1h; Stage #2: With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 3h;	65%

2-aminoethylimidazolidone (6281-42-1) + 4-(benzo[b]thiophen-2-yl)-2-(methylsulfonyl)pyrimidine (893434-89-4) → 1-(2-(4-(benzo[b]thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

Conditions	Yield
With triethylamine In 2-methoxy-ethanol at 100℃;	64%

2-aminoethylimidazolidone (6281-42-1) + 2-{[5-bromo-1-(2-chlorophenyl)-1H-1,2,4-triazol-3-yl]methyl}-5-(4-chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one → 5-(4-chlorophenyl)-2-{[1-(2-chlorophenyl)-5-{[2-(2-oxoimidazolidin-1-yl)ethyl]amino}-1H-1,2,4-triazol-3-yl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3 -one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 150℃; for 5h; Microwave irradiation;	64%

2-aminoethylimidazolidone (6281-42-1) + {4-[2-(2-chloro-5-fluoro-pyrimidin-4-yl)-benzo[b]thiophen-7-yl]-6-fluoro-pyridin-3-ylmethyl}-dimethylamine (1034468-08-0) → 1-(2-{4-[7-(5-((dimethylamino)methyl)-2-fluoro-pyridin-4-yl)benzo[b]thiophen-2-yl]-5-fluoropyrimidin-2-ylamino}ethyl)imidazolidin-2-one (1034466-20-0)

Conditions	Yield
With triethylamine In butan-1-ol at 120℃; for 15h;	63%

2-aminoethylimidazolidone (6281-42-1) + 2-[3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,4-triazol-1-yl]benzoyl chloride → 2-[3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,4-triazol-1-yl]-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h;	61%

2-aminoethylimidazolidone (6281-42-1) + S-allyl isothiouronium hydrobromide (41848-21-9) + hydroquinone (123-31-9) → 2-(allylthio)-5-((2-(2-oxoimidazolidin-1-yl)ethyl)amino)-2,5-cyclohexadiene-1,4-dione

Conditions	Yield
With sodium iodide; sodium chloride In water; acetonitrile at 20℃;	58%

2-aminoethylimidazolidone (6281-42-1) + N-acetyl-O-[bis(benzyloxy)phosphoryl]-L-tyrosine (151608-48-9) → N-acetyl-O-[bis(benzyloxy)phosphoryl]-N'-[2-(2-oxoimidazolidin-1-yl)ethyl]-L-tyrosinamide (1268157-54-5)

Conditions	Yield
Stage #1: N-acetyl-O-[bis(benzyloxy)phosphoryl]-L-tyrosine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-aminoethylimidazolidone In dichloromethane at 0 - 20℃; for 2.16667h; Inert atmosphere;	56%

2-aminoethylimidazolidone (6281-42-1) + p-chlorphenylisocyanate (104-12-1) → 1-[2-(2-Oxo-3-imidazolidinyl)-ethyl]-3-(4-chlorophenyl)urea (63874-81-7)

Conditions	Yield
With triethylamine In toluene at 5℃; for 24h;	53%
In tetrahydrofuran

2-aminoethylimidazolidone (6281-42-1) + 4-(7-bromo-benzo[b]thiophen-2-yl)-2-chloro-5-fluoro-pyrimidine (1034468-28-4) → 1-{2-[4-(7-bromo-benzo[b]thiophen-2-yl)-5-fluoro-pyrimidin-2-ylamino]-ethyl}-imidazolidin-2-one (1034468-55-7)

Conditions	Yield
In 1,4-dioxane at 90℃; for 3h;	52%

2-aminoethylimidazolidone (6281-42-1) + 2-chloro-4-[7-(3-trimethylsilanylethynyl-pyridin-4-yl)-benzo[b]-thiophen-2-yl]-pyrimidine (1034468-45-5) → 1-(2-[4-[7-(3-trimethylsilylethynyl-pyridin-4-yl)-benzo[b]thiophen-2-yl]-pyrimidin-2-ylamino]-ethyl)-imidazolidin-2-one (1034468-65-9)

Conditions	Yield
In butan-1-ol at 120℃; for 4 - 5h;	49%

Upstream product

• 2387-20-4 1-(2-chloroethyl)imidazolidin-2-one 
• 3699-54-5 2-oxo-imidazolidine-1-ethanol 
• 111-40-0 3-azapentane-1,5-diamine 
• 120-93-4 imidazolidone 
• 141-43-5 ethanolamine 
• 107-15-3 ethylenediamine 
• 497-25-6 dimethylenecyclourethane 
• 124-38-9 carbon dioxide 
• 616-38-6 carbonic acid dimethyl ester 
• 757967-03-6 bis-(2-phenylacetylamino-ethyl)-carbamic acid 4-nitro-phenyl ester 
• 57-13-6 urea 
• 40778-59-4 1-(2-aminoethyl)-2-imidazolidinethione 
• 6573-15-5 1,3,6-triazabicyclo[3.3.0]oct-4-ene 

Downstream Products

• 86241-63-6 1-[2-(2-chloro-acetylamino)-ethyl]-imidazolidin-2-one 
• 3089-19-8 N-[2-(2-oxo-imidazolidin-1-yl)-ethyl]-methacrylamide 
• 70209-08-4 3,6-diazanonane-1,9-diamine 
• 123700-21-0 1-<2-<<4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyrid-2-yl>methoxy>ethyl>-3-<2-(2-oxoimidazolidin-1-yl)ethyl>urea 
• 4971-43-1 N-(vinyl)-2-imidazolidinone 
• 63874-81-7 1-[2-(2-Oxo-3-imidazolidinyl)-ethyl]-3-(4-chlorophenyl)urea 
• 137559-77-4 m-TMU 
• 863437-60-9 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide 
• 112-57-2 N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine 
• 111-40-0 3-azapentane-1,5-diamine 
• 3699-54-5 2-oxo-imidazolidine-1-ethanol 
• 111-41-1 2-(2-Aminoethylamino)ethanol 

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