15438-70-7

Basic information

• Product Name: N,N'-BIS(2-HYDROXYETHYL)-UREA
• Synonyms: N,N'-BIS(2-HYDROXYETHYL)-UREA;1,3-Bis(2-hydroxyethyl)urea;2,2'-(Ureylene)diethanol;2,2'-Ureylenediethanol;1,3-Di(beta-hydroxyethyl)urea;Nsc 75436;Urea, 1,3-bis(2-hydroxyethyl)- (8ci);Urea, N,N'-bis(2-hydroxyethyl)-
• CAS NO: 15438-70-7
• Molecular Formula: C₅H₁₂N₂O₃
• Molecular Weight: 148.16
• Mol File: 15438-70-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 83 °C
• Boiling Point: 445.1 °C at 760 mmHg
• Flash Point: 223 °C
• Appearance: /
• Density: 1.226 g/cm³
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly)
• PKA: 13.09±0.46(Predicted)
• CAS DataBase Reference: N,N'-BIS(2-HYDROXYETHYL)-UREA(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-BIS(2-HYDROXYETHYL)-UREA(15438-70-7)
• EPA Substance Registry System: N,N'-BIS(2-HYDROXYETHYL)-UREA(15438-70-7)

Safety Data

• Hazardous Substances Data: 15438-70-7(Hazardous Substances Data)

Usage

Preparation

Excess ethanolamine and DMDTC were mixed and heated at 60℃ for 15 h. The released malodorous methyl sulfide by-product was absorbed and oxidized by NaOCl solution. When the reaction was complete, the unreacted ethanolamine was removed under reduced pressure by simple distillation, leaving a crude mixture of oxazolidinone and bis(2-hydroxyethyl)urea, which was further purified by recrystallization from methanol/ethyl acetate (1:4.5) to give N,N'-bis(2-hydroxyethyl)urea as colorless crystals.

Synthetic route

N-(benzyloxycarbonyl)aniline (3422-02-4) + ethanolamine (141-43-5) → N,N'-bis(2-hydroxyethyl)urea (15438-70-7) + 1-(2-hydroxyethyl)-3-phenylurea (3747-47-5)

Conditions	Yield
With 2-(2-Ethoxyethoxy)ethyl benzyl ether In benzyl alcohol	A n/a B 80%
In benzyl alcohol at 140℃; Rate constant; various temp.,time, and conc.;

S,S-dimethyl dithiocarbonate (868-84-8) + ethanolamine (141-43-5) → dimethylenecyclourethane (497-25-6) + N,N'-bis(2-hydroxyethyl)urea (15438-70-7)

Conditions	Yield
at 60℃; for 15h; Yields of byproduct given;	A n/a B 55%
In methanol at 60℃; for 24h;

carbon dioxide (124-38-9) + ethanolamine (141-43-5) → dimethylenecyclourethane (497-25-6) + N,N'-bis(2-hydroxyethyl)urea (15438-70-7)

Conditions	Yield
With tetrachloromethane; triethylamine; triphenylphosphine In acetonitrile under 760 Torr; for 20h; Ambient temperature;	A 51% B n/a

dimethylenecyclourethane (497-25-6) + ethanolamine (141-43-5) → N,N'-bis(2-hydroxyethyl)urea (15438-70-7)

Conditions	Yield
at 150℃; for 4h;	41%

N-(benzyloxycarbonyl)-N-methylaniline (83330-75-0) → N,N'-bis(2-hydroxyethyl)urea (15438-70-7) + aniline (62-53-3)

Conditions	Yield
In ethanolamine at 140℃; Rate constant; Kinetics; Mechanism; other solvent: ether, various temperatures;

2-hydroxyethyl N-butylcarbamate (13105-54-9) + ethanolamine (141-43-5) → N,N'-di-n-butylurea (1792-17-2) + N,N'-bis(2-hydroxyethyl)urea (15438-70-7) + 1-(2-hydroxyethyl)-3-n-butylurea (29346-52-9)

Conditions	Yield
With caesium carbonate at 100℃; for 0.5h;	A 17 %Chromat. B 12 %Chromat. C 45 %Chromat.

β-hydroxyethyl benzylcarbamate (4663-83-6) + ethanolamine (141-43-5) → N,N'-bis(2-hydroxyethyl)urea (15438-70-7) + 1,3-dibenzylurea (1466-67-7) + N-(2-hydroxyethyl)-N'-benzylurea (57501-19-6)

Conditions	Yield
With caesium carbonate at 100℃; for 0.5h;	A 18 %Chromat. B 19 %Chromat. C 35 %Chromat.

1,3-bis(2-((triethylsilyl)oxy)ethyl)urea (1310688-13-1) → N,N'-bis(2-hydroxyethyl)urea (15438-70-7)

Conditions	Yield
With potassium carbonate In methanol at 80℃; for 1h; Inert atmosphere;

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → 1,3-bis(2-hydroxyethyl)-1-nitrosourea (75014-24-3)

Conditions	Yield
With sodium acetate; dinitrogen tetraoxide In dichloromethane for 1h; Ambient temperature;

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) + (allyloxy)bis(diisopropylamino)phosphine (108554-72-9) → C23H48N4O5P2 (1163120-83-9)

Conditions	Yield
With pyridinium trifluroacetate In acetonitrile at 18.4 - 25.6℃; for 17 - 18h; Product distribution / selectivity;

C39H77N2O7P (918826-72-9) + N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C71H136N4O17P2 + C38H74N3O10P

Conditions	Yield
Stage #1: C39H77N2O7P With acetic acid In acetonitrile at 0 - 25℃; Stage #2: N,N'-bis(2-hydroxyethyl)urea With pyridinium trifluroacetate In acetonitrile at 20℃; for 18h;

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C7H5O2(1-)*C19H10F8I2N2O5

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C7H5O2(1-)*C19H10F10N2O5

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F8I2N2O5*Cl(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutyl-ammonium chloride / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F10N2O5*Cl(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutyl-ammonium chloride / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F8I2N2O5*H2O4P(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutylammonium dihydrogen phosphate / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F10N2O5*H2O4P(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutylammonium dihydrogen phosphate / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → Br(1-)*C19H10F8I2N2O5

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutylammomium bromide / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → Br(1-)*C19H10F10N2O5

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutylammomium bromide / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F8I2N2O5*I(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetra-(n-butyl)ammonium iodide / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F10N2O5*I(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetra-(n-butyl)ammonium iodide / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C7H7O3S(1-)*C19H10F8I2N2O5

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C7H7O3S(1-)*C19H10F10N2O5

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F8I2N2O5*HO4S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetra(n-butyl)ammonium hydrogensulfate / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F10N2O5*HO4S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetra(n-butyl)ammonium hydrogensulfate / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F8I2N2O5*NO3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutylammonium nitrate / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) → C19H10F10N2O5*NO3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 75 °C / Inert atmosphere 2: tetrabutylammonium nitrate / acetonitrile / 21.84 °C / Inert atmosphere View Scheme

N,N'-bis(2-hydroxyethyl)urea (15438-70-7) + Pentafluorobenzoic acid (602-94-8) → (carbonylbis(azanediyl))bis(ethane-2,1-diyl) bis(2,3,4,5,6-pentafluorobenzoate) (1310688-46-0)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 75℃; for 24h; Inert atmosphere;	312 mg

Upstream product

• 497-25-6 dimethylenecyclourethane 
• 141-43-5 ethanolamine 
• 13105-54-9 2-hydroxyethyl N-butylcarbamate 
• 4663-83-6 β-hydroxyethyl benzylcarbamate 
• 1310688-13-1 1,3-bis(2-((triethylsilyl)oxy)ethyl)urea 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 124-38-9 carbon dioxide 
• 83330-75-0 N-(benzyloxycarbonyl)-N-methylaniline 

Downstream Products

• 1310688-46-0 (carbonylbis(azanediyl))bis(ethane-2,1-diyl) bis(2,3,4,5,6-pentafluorobenzoate) 
• 1310688-44-8 (carbonylbis(azanediyl))bis(ethane-2,1-diyl) bis(2,3,4,5-tetrafluoro-6-iodobenzoate) 
• 2214-72-4 1,3-bis(2-chloroethyl)urea 

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