2078-71-9

Basic information

• Product Name: 2-HYDROXYETHYLUREA
• Synonyms: (2-hydroxyethyl)-ure;(beta-Hydroxyethyl)urea;1-Ethanolurea;hydroxyethylurea;Monoethanolurea;Monoethylolurea;N-(beta-Hydroxyethyl)urea;Urea, (2-hydroxyethyl)-
• CAS NO: 2078-71-9
• Molecular Formula: C₃H₈N₂O₂
• Molecular Weight: 104.11
• EINECS: 1592732-453-0
• Product Categories: Carbonyl Compounds;Organic Building Blocks;Ureas;Cosmetic
• Mol File: 2078-71-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 164-169 °C(lit.)
• Boiling Point: 254.324 °C at 760 mmHg
• Flash Point: 107.612 °C
• Appearance: White crystalline powder
• Density: 1.222 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.35±0.46(Predicted)
• Water Solubility: almost transparency
• CAS DataBase Reference: 2-HYDROXYETHYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYETHYLUREA(2078-71-9)
• EPA Substance Registry System: 2-HYDROXYETHYLUREA(2078-71-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: YT4907000
• Hazardous Substances Data: 2078-71-9(Hazardous Substances Data)

Usage

Uses

1-(2-Hydroxyethyl)urea is used as a reactant in the application of fluorous protocols for Ugi and Biginelli multicomponent condensations.

InChI:InChI=1S/C3H8N2O2/c4-3(7)5-1-2-6/h6H,1-2H2,(H3,4,5,7)

Synthetic route

<2-(trimethylsilyloxy)ethyl>urea (75226-85-6) → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
With methanol; water for 1h; Heating;	100%

N-<2-(trimethylsiloxy)ethyl>-N'-(trimethylsilyl)urea (75226-87-8) → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
With methanol; water for 1h; Heating;	100%

nitrourea (556-89-8) + ethanolamine (141-43-5) → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
In ethanol for 48h;	85%

potassium cyanate (590-28-3) + ethanolamine (141-43-5) → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
Stage #1: potassium cyanate; ethanolamine In water for 0.333333h; Heating; Stage #2: With hydrogenchloride In water at 20℃; for 7h;	80%
With hydrogenchloride In water

ethanolamine (141-43-5) + urea (57-13-6) → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
With ammonia In formic acid at 115℃; for 3.5h; Temperature; Industrial scale;	78%
In N,N-dimethyl-formamide at 105℃; for 24h;

2-amino-ethanol hydrochloride (2002-24-6) + potassium cyanide (151-50-8) → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
In water at 85 - 90℃; for 1h;	68%
In water

oxirane (75-21-8) + urea (57-13-6) → dimethylenecyclourethane (497-25-6) + (2-hydroxyethyl)urea (2078-71-9) + carbamic acid-(2-amino-ethyl ester) (142-27-8)

Conditions	Yield
at 136℃;

oxirane (75-21-8) + urea (57-13-6) → (2-hydroxyethyl)urea (2078-71-9) + carbamic acid-(2-amino-ethyl ester) (142-27-8)

Conditions	Yield
at 136℃;

2,4-imidazolidinedione (461-72-3) → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
With sodium tetrahydroborate In ethanol

potassium cyanate (590-28-3) + hydrochloride of β-oxy-ethylamine → (2-hydroxyethyl)urea (2078-71-9)

2-amino-ethanol hydrochloride (2002-24-6) + sodium cyanate → (2-hydroxyethyl)urea (2078-71-9)

Conditions	Yield
mit hilfe eines Ionen-Austauschers;

(2-hydroxyethyl)urea (2078-71-9) + bis(tri-n-butyltin)oxide (56-35-9) → N-(tributylstannyl)-N'-(2-(tributylstannyloxy)ethyl)urea (104585-96-8)

Conditions	Yield
In neat (no solvent) byproducts: H2O; at 160-190°C, evacuation down to 2mm for 1 h; elem. anal.;	95%

(2-hydroxyethyl)urea (2078-71-9) + C17H16N2O3 → C20H22N4O4

Conditions	Yield
With hydrogenchloride; water In isopropyl alcohol for 0.333333h; Reflux; regioselective reaction;	93%

(2-hydroxyethyl)urea (2078-71-9) + 1,3-dimethyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-one (66242-64-6) → C20H22N4O3

Conditions	Yield
With hydrogenchloride In methanol; water for 1h; Reflux;	90%

(2-hydroxyethyl)urea (2078-71-9) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) → 4,6-diethyl-1-(2-hydroxyethyl)-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-2-one (1346780-34-4)

Conditions	Yield
With hydrogenchloride In methanol; water for 2h; Reflux;	90%

(2-hydroxyethyl)urea (2078-71-9) + 1-ethyl-5-hydroxy-4,5-diphenyl-1H-imidazol-2(5H)-one → 1-ethyl-6-(2-hydroxyethyl)-3a,6a-diphenyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Conditions	Yield
With hydrogenchloride In water; acetonitrile for 0.333333h; Reflux; regioselective reaction;	76%

(2-hydroxyethyl)urea (2078-71-9) + 5-hydroxy-4,5-diphenyl-1-propyl-1H-imidazol-2(5H)-one → 1-(2-hydroxyethyl)-3a,6a-diphenyl-6-propyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Conditions	Yield
With hydrogenchloride In water; acetonitrile for 0.333333h; Reflux; regioselective reaction;	74%

(2-hydroxyethyl)urea (2078-71-9) + 4,4'-dimethoxybenzoin (119-52-8) → 1-(2-hydroxyethyl)-4,5-bis(4-methoxyphenyl)-1H-imidazol-2(3H)-one

Conditions	Yield
With ethylene glycol at 160℃; for 1h;	70%

(2-hydroxyethyl)urea (2078-71-9) + 4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione (1195504-76-7) → 1-(2-hydroxyethyl)-4,6-dimethyl-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-2-one (1346780-20-8)

Conditions	Yield
With hydrogenchloride In methanol; water for 2h; Reflux;	68%

(2-hydroxyethyl)urea (2078-71-9) + benzil (134-81-6) → C20H22N4O4

Conditions	Yield
With hydrogenchloride; water In isopropyl alcohol for 2h; Reflux; regioselective reaction;	68%

(2-hydroxyethyl)urea (2078-71-9) + ethyl 2-cyanoacetate (105-56-6) → 6-amino-1-β-hydroxyethyluracil (56075-69-5)

Conditions	Yield
With sodium In ethanol for 10h; Heating;	67%
With sodium In ethanol Cooling with ice; Reflux;	59.4%
With ethanol; sodium ethanolate

(2-hydroxyethyl)urea (2078-71-9) + 4,5-dihydroxy-2-imidazolidinone (3720-97-6) → (1R*,5S*)-2-(2-hydroxyethyl)-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

Conditions	Yield
With hydrogenchloride In water for 1h; pH=1 - 2; Heating;	55%

(2-hydroxyethyl)urea (2078-71-9) + 4,5-dihydroxy-2-imidazolidinone (3720-97-6) → 2,4-imidazolidinedione (461-72-3) + 2-(2-hydroxyethyl)-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (125577-52-8)

Conditions	Yield
With hydrogenchloride In water at 85℃; for 1h; pH=1 - 2;	A n/a B 55%

(2-hydroxyethyl)urea (2078-71-9) + 1-benzyl-3,5-dichloro-6-methylpyrazin-2(1H)-one (173200-35-6) → 1-(4-benzyl-6-chloro-5-methyl-3-oxo-3,4-dihydropyrazin-2-yl)-3-(2-hydroxyethyl)urea

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,2-dimethoxyethane at 80 - 100℃; Microwave irradiation;	50%

(2-hydroxyethyl)urea (2078-71-9) + 2,2-dimethylpenta-3,4-dienal oxime (913260-88-5) + benzaldehyde (100-52-7) → N-[2-({3,3-dimethyl-1-oxido-5-[(E)-2-(phenyl)vinyl]-3,4-dihydro-2H-pyrrol-2-yl}oxy)ethyl]urea (1376476-82-2)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 2.5h; Inert atmosphere;	46%

(2-hydroxyethyl)urea (2078-71-9) → 3-Nitrosooxazolidin-2-one (38347-74-9)

Conditions	Yield
With nitrosylchloride In chloroform	42%
With nitrosylchloride In chloroform at 0℃; Product distribution; other reagents;	42%

(2-hydroxyethyl)urea (2078-71-9) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → trimethylsilyl isocyanate (1118-02-1) + N-<2-(trimethylsiloxy)ethyl>-N'-(trimethylsilyl)urea (75226-87-8)

Conditions	Yield
With sulfuric acid at 120 - 152℃; for 6h;	A 39% B 36%

methanol (67-56-1) + (2-hydroxyethyl)urea (2078-71-9) + benzil (134-81-6) → C18H18N2O3 + C20H22N4O4

Conditions	Yield
With hydrogenchloride; water for 2h; Reflux; diastereoselective reaction;	A 38% B 14%

Upstream product

• 590-28-3 potassium cyanate 
• 2002-24-6 2-amino-ethanol hydrochloride 
• 141-43-5 ethanolamine 
• 57-13-6 urea 
• 75226-87-8 N-<2-(trimethylsiloxy)ethyl>-N'-(trimethylsilyl)urea 
• 75226-85-6 <2-(trimethylsilyloxy)ethyl>urea 
• 556-89-8 nitrourea 
• 151-50-8 potassium cyanide 
• 461-72-3 2,4-imidazolidinedione 
• 75-21-8 oxirane 

Downstream Products

• 40380-05-0 (2-bromo-ethyl)-urea 
• 15025-32-8 β-Ureido-ethanol-O.N-bis-p-nitrobenzoat 
• 625-52-5 N-Ethylurea 
• 497-25-6 dimethylenecyclourethane 

Relevant articles and documents

Synthesis and Structure of 1-Substituted Semithioglycolurils

Two methods for the synthesis of previously unavailable 1-substituted semithioglycolurils were developed. These methods consist of the cyclocondensation of 1-substituted ureas with 4,5-dihydroxy- or 4,5-dimethoxyimidazolidine-2-thione or glyoxal, followed by the reaction of the resulting 1-substituted 4,5-dihydroxyimidazolidine-2-ones with HSCN in a two-step one-pot procedure. Two of the desired semithioglycolurils were obtained as conglomerates.

The ethylenically unsaturated group-containing isocyanate compound

PROBLEM TO BE SOLVED: To provide a production method capable of obtaining an ethylenically unsaturated group-containing isocyanate compound with high yield, which is excellent in safety to human bodies or environments without using phosgene and in which the production processes and production facilities are simplified.SOLUTION: There is a method for producing an ethylenically unsaturated group-containing isocyanate compound which produces a compound having an ethylenically unsaturated bond and an isocyanate group in the molecule using an amino alcohol as a raw material, wherein the method has a step of producing a cyclic compound having a urethane bond in the molecule as an intermediate.

Synthesis of 2-monofunctionalized 2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7- diones

New (1R*,5S*)-2-R-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7- diones containing the terminal carboxy or hydroxy group in the substituent R were synthesized by cyclocondensation of 4,5-dihydroxyimidazolidin-2-one with 1-R-ureas. Single-crystal X-ray diffraction analysis showed that 2-carboxyethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione crystallizes as a racemate.