4097-89-6

Basic information

• Product Name: TRIS(2-AMINOETHYL)AMINE
• Synonyms: tris(aminoethyl)amine;tris(beta-aminoethyl)amine;2,2',2''-Triaminotriethylamine,97%TREN;2,2'',2 -TRIAMINOTRIETHYLAMINE TREN;2,2μ,2μμ-Nitrilotriethylamine, 2,2μ,2μμ-Triaminotriethylamine, TAEA;2,2',2''-Nitrilotris(ethane-1-amine);2,2',2''-Nitrilotrisethanamine;Tris(2-aminoethyl)amine,96%
• CAS NO: 4097-89-6
• Molecular Formula: C₆H₁₈N₄
• Molecular Weight: 146.23
• EINECS: 223-857-4
• Mol File: 4097-89-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: -16 °C
• Boiling Point: 114 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/saline suspension
• Density: 0.976 g/mL at 20 °C(lit.)
• Vapor Density: 5 (vs air)
• Vapor Pressure: 0.02 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.497(lit.)
• Storage Temp.: 2-8°C
• PKA: 10.00±0.10(Predicted)
• Water Solubility: Miscible with water.
• Sensitive: Hygroscopic
• Stability: Stable. Hygroscopic. Absorbs carbon dioxide from the air. Incompatible with strong acids, strong oxidizing agents.
• BRN: 1739626
• CAS DataBase Reference: TRIS(2-AMINOETHYL)AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(2-AMINOETHYL)AMINE(4097-89-6)
• EPA Substance Registry System: TRIS(2-AMINOETHYL)AMINE(4097-89-6)

Safety Data

• Hazard Codes: T,Xi
• Statements: 22-24-34-36/37/38-10
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: KH8587082
• F: 3-10-23
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 4097-89-6(Hazardous Substances Data)

Usage

Description

Tris(2-aminoethyl)amine (TREN) is a water-soluble tripodal ligand that is predominantly utilized in coordination chemistry. It features three aminoethyl groups that attach to surface atoms, providing a scaffold assembly. As a tetradentate chelating ligand, it forms stable complexes with transition metals and exhibits a colorless liquid appearance.

Uses

Used in Coordination Chemistry:
Tris(2-aminoethyl)amine is used as a tetradentate chelating ligand for forming stable complexes with transition metals. This application is crucial in various chemical reactions and processes that involve metal coordination.
Used as a Carbon Dioxide Absorbent:
Tris(2-aminoethyl)amine serves as a carbon dioxide absorbent, making it a valuable component in industries where CO2 removal is essential, such as in the medical field for respirator applications or in industrial processes to control greenhouse gas emissions.
Used in Peptide Synthesis:
In the field of peptide synthesis, Tris(2-aminoethyl)amine acts as a reagent for the cleavage of the fluorenylmethyloxycarbonyl (Fmoc) group. This function is vital for the synthesis of peptides and proteins, as it allows for the selective removal of protecting groups during the assembly process.
Used in the Synthesis of Tris-urea and -thiourea Derivatives:
Tris(2-aminoethyl)amine is also utilized in the reaction with aryl isocyanates and isothiocyanates to produce tris-urea and -thiourea derivatives. These derivatives have potential applications in various fields, including pharmaceuticals and materials science.

Hazard

A poison by ingestion and skin contact.

Safety Profile

A poison by ingestion and skin contact. When heated to decomposition it emits toxic vapors of NOx.

Purification Methods

For a separation from a mixture containing 62% TRIEN, see entry under triethylenetetramine. Also purify it by conversion to the hydrochloride (see below), recrystallise it and regenerate the free base [Xie & Hendrickson J Am Chem Soc 109 6981 1987]. [Beilstein 4 H 256, 4 II 695, 4 III 545, 4 IV 1250.]

InChI:InChI=1/C6H18N4/c7-1-4-10(5-2-8)6-3-9/h1-9H2/p+4

Upstream product

• 817-09-4 tris-(2-chloroethyl)amine hydrochloride 
• 102-71-6 triethanolamine 
• 147631-19-4 (CH₃)3CGe(NHCH₂CH₂)3N 
• 147631-17-2 CH₃Ge(NHCH₂CH₂)3N 
• 151-56-4 ethyleneimine 
• 111-40-0 3-azapentane-1,5-diamine 
• 107-06-2 1,2-dichloro-ethane 
• 44905-58-0 triaminotriethylamine hydrogen chloride 

Downstream Products

• 141621-34-3 C₃₀H₃₀N₄O₉ 
• 139112-38-2 1,1',1''-(nitrilotris(ethane-2,1-diyl))tris(1H-pyrrole-2,5-dione) 
• 129323-91-7 N,N-Bis(2-aminoethyl)-N'-cyclohexyl-1,2-Ethanediamine 
• 129323-74-6 tris-(N-cyclohexyl-2-aminoethyl)amine 
• 70292-82-9 tris{2-[(3,5-dichlorosalicylidene)amino]ethyl}amine 
• 684236-36-0 bis(2-(bis(4-methoxybenzenesulfonyl)amino)ethyl)-(2-(4-methoxybenzenesulfonamido)ethyl)amine 
• 630414-69-6 N¹,N¹-bis(2-aminoethyl)-N²-(trityl)-1,2-ethanediamine 
• 614753-10-5 4-{1-[4-({2-[bis-(2-amino-ethyl)-amino]-ethylamino}-methyl)-benzyl]-5,6-dichloro-1H-benzoimidazol-2-yl}-piperidine-1-carboxylic acid tert-butyl ester 
• 566201-39-6 C₆₉H₁₀₂N₁₀O₂₁ 

Relevant articles and documents

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N - alkylated three amidogen star-shaped ultra-low molecular inhibitors of preparation method

The invention discloses a N - alkylated three amidogen star-shaped ultra-low molecular inhibitors of the preparation method, the method using triethanolamine as raw materials, in solution to the triethanolamine sequentially carry out the oxidation reaction, amination reaction, so as to obtain the final product The process of the invention is simple, low cost, mild condition, the safety is good, high yield, is suitable for industrial production. The invention prepared three amidogen N - alkylation of star-shaped ultra-low molecular inhibitor molecule with the size of the structure can be accurately controlled, the terminal group to a primary amine group and group large characteristic of the density, the bentonite and be better hydration of the stolen are there is a strong function of inhibiting, at a relatively low quantity that can effectively inhibit hydration under expansion, has strong of temperature performance, which is capable of reach 220 °C.

Tris(2-aminoethyl)amine synthesis process

The invention discloses a tris(2-aminoethyl)amine synthesis process, and belongs to the technical field of compound preparation. The tris(2-aminoethyl)amine synthesis process includes the steps of taking triethanolamine as a starting material, putting the triethanolamine, thionyl chloride and a catalyst DMF in a reactor, heating the three to generate tris(2-chloroethyl)amine hydrochloride, dissolving separated tris(2-chloroethyl)amine hydrochloride concentrate and ammonia water in an organic solvent in a reactor, putting the solution in the reactor, carrying out a reaction while heating to obtain tris(2-aminoethyl)amine hydrochloride, and reacting the tris(2-aminoethyl)amine hydrochloride with sodium hydroxide to obtain the tris(2-aminoethyl)amine. The tris(2-aminoethyl)amine synthesis process has the advantages of short reaction route and high controllability.

Synthesis and interconversions of azagermatranes

The syntheses of the first examples of the title compounds, namely, ZGe(NRCH2CH2)3N (4, R = H, Z = Me; 5, R = Me, Z = Me; 6, R = H, Z = t-Bu; 7, R = Me, Z = t-Bu; 8, R = Me, Z = NMe2) are reported. Syntheses of the new compounds MeGe(NMe2)3 and t-BuGe(NMe2)3 and an improved synthesis of Ge(NMe2)4 are also recorded. The azagermatranes 5 and 7 are transformed to 4 and 6, respectively, in the presence of (H2NCH2CH2)3N. This reaction was not found to be reversible, however. Azagermatranes 4 or 5 and 6 or 7 in the presence of (HOCH2CH2)3N easily react to give MeGe(OCH2CH2)3N and t-BuGe(OCH2CH2)3N, respectively. Because of steric factors, one or more of compounds 6-8 may display weakened transannular Ge←N bonding or even an absence of this bonding.