Tris(2-aminoethyl)amine

Tris(2-aminoethyl)amine
Names
IUPAC name
N,N-Bis(2-aminoethyl)-1,2-ethanediamine
Other names
  • 2,2′,2′′-Nitrilotriethylamine
  • 2,2′,2′′-Triaminotriethylamine
  • TAEA
Identifiers
3D model (JSmol)
1739626
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.021.689
EC Number 223-857-4
27074
MeSH Tris(2-aminoethyl)amine
RTECS number KH8587082
UN number 2922
Properties
C6H18N4
Molar mass 146.24 g·mol−1
Appearance Colorless liquid
Odor Ichtyal, ammoniacal
Density 0.976 g/mL (20 °C)[1]
Melting point −16 °C (3 °F; 257 K)
Boiling point 265 °C (509 °F; 538 K)
Miscible
log P −2.664
Vapor pressure 3 Pa (at 20 °C)
1.497[1]
Thermochemistry
−74.3–−72.9 kJ mol−1
−4860.6–−4859.2 kJ mol−1
Hazards
Safety data sheet fishersci.com
GHS pictograms
GHS signal word DANGER
H301, H310, H314
P280, P302+350, P305+351+338, P310
Flash point 113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
  • 117 mg kg−1 (dermal, rabbit)
  • 246 mg kg−1 (oral, rat)
Related compounds
Related amines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Tren is a C3-symmetric, 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.[2] In contrast, for [Co(trien)X2]+ five diastereomers 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).

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.[3] Tren is a common impurity in the more common triethylenetetramine ("trien"). As a trifunctional amine, tren forms a triisocyanate when derivatized with COCl2.[4]

Safety considerations

(NH2CH2CH2)3N, like other polyamines, is corrosive.[5]

References

  1. 1 2 "Tris(2-aminoethyl)amine". Sigma-Aldrich.
  2. ↑ Donald A. House "Ammonia & N-donor Ligands" in Encyclopedia of Inorganic Chemistry John Wiley & Sons, 2006. doi:10.1002/0470862106.ia009.
  3. ↑ 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
  4. ↑ Pressure Chemical
  5. ↑ The Physical and Theoretical Chemistry Laboratory Oxford University MSDS
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