Tris(2-aminoethyl)amine

Tris(2-aminoethyl)amine
Tris(2-aminoethyl)amine
Identifiers
CAS number 4097-89-6 YesY
PubChem 77731
RTECS number KH8587082
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
Hazards
MSDS Fisher Scientifc MSDS
R-phrases 22-24-34
S-phrases 26-36/37/39-45
Main hazards Corrosive
 YesY (verify) (what is: YesY/N?)
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.

Structures of trigonal bipyramidal and octahedral complexes of the formulae M(tren)X (left, C3v symmetry) and M(tren)X2 (right, Cs symmetry).

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

  1. ^ Donald A. House “Ammonia & N-donor Ligands” in Encyclopedia of Inorganic Chemistry John Wiley & Sons, 2006. doi:10.1002/0470862106.ia009.
  2. ^ R. Morassi, L. Sacconi "Tetradentate Tripod Ligands Containing Nitrogen, Sulfur, Phosphorus, and Arsenic as Donor Atoms" Inorganic Syntheses, 1976, vol. 16 p. 174-180. doi:10.1002/9780470132470.ch47
  3. ^ Pressure Chemical
  4. ^ The Physical and Theoretical Chemistry Laboratory Oxford University MSDS

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