Tris(2-aminoethyl)amine
| Tris(2-aminoethyl)amine | |
|---|---|
| File:Tris(2-aminoethyl)amine.svg | |
| Tris(2-aminoethyl)amine | |
| Other names 2,2',2-Nitrilotriethylamine 2,2',2-Triaminotriethylamine TAEA 4-(2-aminoethyl)diethylenetriamine nitrilotris(ethylamine) tris(aminoethyl)amine tris(beta-aminoethyl)amine Tren | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 4097-89-6 |
| PubChem | 77731 |
| RTECS number | KH8587082 |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | (NH2CH2CH2)3N |
| Molar mass | 146.236 g/mol |
| Appearance | colourless |
| Density | 0.977 g/cm3 |
| Melting point |
−16 °C |
| Boiling point |
265 °C |
| Solubility in water | miscible |
| Solubility | polar organic solvents |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| MSDS | Fisher Scientifc MSDS |
| R-phrases | 22-24-34 |
| S-phrases | 26-36/37/39-45 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Tris(2-aminoethyl)amine is the organic compound with the formula N(CH2CH2NH2)3. This colourless liquid is soluble in water and is highly basic, consisting of a tertiary amine center and three pendant primary amine groups. Abbreviated "tren," it is the archetypal tripodal ligand of interest in coordination chemistry.
Contents
Coordination chemistry
Tren is a tripodal, tetradentate chelating ligand that forms stable complexes with transition metals, especially those in the 2+ and 3+ oxidation states. Tren complexes exist with relatively few isomers, reflecting the constrained connectivity of this tetramine. Thus, only a single achiral stereoisomer exists for [Co(tren)X2]+, where X is halide or pseudohalide.[1] In contrast, for [Co(trien)X2]+ five diastereoiomers are possible, four of which are chiral. In a few cases, tren serves as a tridentate ligand with one of the primary amine groups non-coordinated.
Related tripodal ligands
The permethylated derivative of tren is also well known. With the formula N(CH2CH2NMe2)3, "Me6tren," forms a variety of complexes but, unlike tren, does not stabilize Co(III). Related amino-triphosphines are also well developed, such as N(CH2CH2PPh2)3 (m.p. 101-102 °C). This species is prepared from the nitrogen mustard N(CH2CH2Cl)3.[2]
The tripodal ligand of greatest commercial significance is nitrilotriacetate, N(CH2CO2-)3.
Organic chemistry
Tren is a common impurity in the more common triethylenetetramine ("trien"). As a trifunctional amine, tren forms a triisocyanate when derivatized with COCl2.[3]
Safety considerations
(NH2CH2CH2)3N, like other polyamines, is corrosive.[4]
References
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