1965-29-3

Basic information

• Product Name: 2-(2-(2-aminoethylamino)ethylamino)ethanol
• Synonyms: 2-(2-(2-aminoethylamino)ethylamino)ethanol;HYDROXYETHYLDIETHYLENETRIAMINE;N-2-HYDROXYETHYL-DIETHYLENETRIAMINE;2-Ethanediamine, N-(2-aminoethyl)-N'-(2-hydroxyethyl)-1;n-(2-hydroxyethyl)-diethylenetriamin;N-(hydroxyethyl)diethylenetriamine;3,6,9-Triaza-1-nonanol;N-(2-Hydroxyethyl)-N'-(2-aminoethyl)ethylenediamine
• CAS NO: 1965-29-3
• Molecular Formula: C₆H₁₇N₃O
• Molecular Weight: 147.21868
• EINECS: 217-811-2
• Mol File: 1965-29-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 290℃
• Flash Point: 129℃
• Appearance: /
• Density: 1.005
• Vapor Pressure: 0.000238mmHg at 25°C
• Refractive Index: 1.4974
• CAS DataBase Reference: 2-(2-(2-aminoethylamino)ethylamino)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-(2-aminoethylamino)ethylamino)ethanol(1965-29-3)
• EPA Substance Registry System: 2-(2-(2-aminoethylamino)ethylamino)ethanol(1965-29-3)

Safety Data

• Hazardous Substances Data: 1965-29-3(Hazardous Substances Data)

Usage

General Description

2-(2-(2-aminoethylamino)ethylamino)ethanol, also known as triethanolamine, is a chemical compound with the molecular formula C6H15NO3. It is a colorless and odorless liquid that is commonly used as an ingredient in various cosmetic and personal care products, such as shampoos, soaps, and lotions, as well as in industrial applications like metalworking fluids and textile processing. Triethanolamine is primarily used as a surfactant, emulsifier, and pH adjuster in these products, helping to stabilize mixtures and maintain the desired pH level. While it is generally regarded as safe for use in small concentrations, it can cause skin and eye irritation in higher concentrations and is regulated in some countries due to potential health risks.

InChI:InChI=1/C6H17N3O/c7-1-2-8-3-4-9-5-6-10/h8-10H,1-7H2

Synthetic route

oxirane (75-21-8) + 1,5-diamino-3-azapentane (111-40-0) → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3)

Conditions	Yield
With water

2-bromoethylamine hydrobromide (2576-47-8) + 2-(2-Aminoethylamino)ethanol (111-41-1) → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3)

Conditions	Yield
With water

1,5-diamino-3-azapentane (111-40-0) + 2-chloro-ethanol (107-07-3) → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3)

Conditions	Yield
In water
Stage #1: 3-azapentane-1,5-diamine; 2-chloro-ethanol In water for 8h; Reflux; Stage #2: With potassium carbonate In methanol for 0.5h;

acetate of N--glycine ethyl ester → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

tetrahydrofuran (109-99-9) + [2-(2-Amino-acetylamino)-acetylamino]-acetic acid ethyl ester (16195-08-7) + LiAlH4 → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3)

Conditions	Yield
das Acetat reagiert;

ethylenediamine (107-15-3) + 2,2'-iminobis[ethanol] (111-42-2) → 2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine (112-57-2)

Conditions	Yield
With imidazolidone at 270℃; for 5h; Inert atmosphere;

2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + bromoacetic acid tert-butyl ester (5292-43-3) → di-tert-butyl 2,2'-((2-((2-(tert-butoxy)-2-oxoethyl)(2-((2-(tert-butoxy)-2-oxoethyl)(2-hydroxyethyl)amino)ethyl)amino)ethyl)azanediyl)diacetate

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	60%

2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + 1,2-dioleoyl-sn-glycero-3-phosphocholine (74493-34-8) → dioleoylphosphate-triethylenetriamine

Conditions	Yield
With Phospholipase D In ethyl acetate at 40℃; for 72h; Enzymatic reaction;	3%

2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + n-octyl chloroacetate (5451-98-9) → ([2-(Bis-octyloxycarbonylmethyl-amino)-ethyl]-{2-[(2-hydroxy-ethyl)-octyloxycarbonylmethyl-amino]-ethyl}-amino)-acetic acid octyl ester (51992-90-6)

Conditions	Yield
With potassium carbonate

2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + chloroacetic acid ethyl ester (105-39-5) → ([2-(Bis-ethoxycarbonylmethyl-amino)-ethyl]-{2-[ethoxycarbonylmethyl-(2-hydroxy-ethyl)-amino]-ethyl}-amino)-acetic acid ethyl ester (51992-89-3)

Conditions	Yield
With potassium carbonate

2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + 1,4,5,8-tetrahydroxy-2,3-dihydro-9,10-anthracenedione (81-59-4) → 1,4-Dihydroxy-5,8-bis-{2-[2-(2-hydroxy-ethylamino)-ethylamino]-ethylamino}-anthraquinone

Conditions	Yield
(i) Me2NCH2CH2NMe2, (ii) 2,3,5,6-tetrachloro-<1,4>benzoquinone, MeOCH2CH2OH; Multistep reaction;

2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) → 2,2'-((2-((carboxymethyl)(2-((carboxymethyl)(2-hydroxyethyl)amino)ethyl)amino)ethyl)azanediyl)diacetic acid bis(trifluoroacetic acid) salt

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: dichloromethane / 24 h / 0 - 20 °C View Scheme

2-[2-(2-aminoethylamino)ethylamino]ethanol (1965-29-3) + methyl 2,4,4,5,7,7,8,8,9,9,9-undecafluoro-2,5-bis(trifluoromethyl)-3,6-dioxanonanoate (26131-32-8) → C31H14F47N3O10

Conditions	Yield
In dichloromethane for 10h; Cooling with ice;

Upstream product

• 2576-47-8 2-bromoethylamine hydrobromide 
• 111-41-1 2-(2-Aminoethylamino)ethanol 
• 109-99-9 tetrahydrofuran 
• 16195-08-7 [2-(2-Amino-acetylamino)-acetylamino]-acetic acid ethyl ester 
• 107-15-3 ethylenediamine 
• 111-42-2 2,2'-iminobis[ethanol] 
• 111-40-0 3-azapentane-1,5-diamine 
• 107-07-3 2-chloro-ethanol 
• 75-21-8 oxirane 

Relevant articles and documents

Thermodynamic, Spectroscopic, and Computational Studies of f-Element Complexation by N-Hydroxyethyl-diethylenetriamine-N,N′,N,N-tetraacetic Acid

Potentiometric and spectroscopic techniques were combined with DFT calculations to probe the coordination environment and determine thermodynamic features of trivalent f-element complexation by N-hydroxyethyl-diethylenetriamine-N,N′,N,N-tetraacetic acid, HEDTTA. Ligand protonation constants and lanthanide stability constants were determined using potentiometry. Five protonation constants were accessible in I = 2.0 M (H+/Na+)ClO4. UV-vis spectroscopy was used to determine stability constants for Nd3+ and Am3+ complexation with HEDTTA. Luminescence spectroscopy indicates two water molecules in the inner coordination sphere of the Eu/HEDTTA complex, suggesting HEDTTA is heptadentate. Luminescence data was supported by DFT calculations, which demonstrate that substitution of the acetate pendant arm by a N-hydroxyethyl group weakens the metal-nitrogen bond. This bond elongation is reflected in HEDTTA’s ability to differentiate trivalent actinides from trivalent lanthanides. The trans-lanthanide Ln/HEDTTA complex stability trend is analogous to Ln/DTPA complexation; however, the loss of one chelate ring resulting from structural substitution weakens the complexation by ～3 orders of magnitude. Successful separation of trivalent americium from trivalent lanthanides was demonstrated when HEDTTA was utilized as aqueous holdback complexant in a liquid-liquid system. Time-dependent extraction studies for HEDTTA were compared to diethylenetriamine-N,N,N′,N,N-pentaacetic acid (DTPA) and N-hydroxyethyl-ethylenediamine-N,N′,N′-triacetic acid (HEDTA). The results indicate substantially enhanced phase-transfer kinetic rates for mixtures containing HEDTTA.