1,1,1-Tris(aminomethyl)ethane

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1,1,1-Tris(aminomethyl)ethane
Names
Preferred IUPAC name
2-(Aminomethyl)-2-methylpropane-1,3-diamine
Other names
TAME
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.149.897 Edit this at Wikidata
  • InChI=1S/C5H15N3/c1-5(2-6,3-7)4-8/h2-4,6-8H2,1H3
    Key: UGDSCHVVUPHIFM-UHFFFAOYSA-N
  • InChI=1/C5H15N3/c1-5(2-6,3-7)4-8/h2-4,6-8H2,1H3
    Key: UGDSCHVVUPHIFM-UHFFFAOYAE
  • CC(CN)(CN)CN
Properties
CH3C(CH2NH2)3
Molar mass 117.20
Appearance Colorless liquid
Density 1.0 g/cm3
Boiling point 264.0 °C (507.2 °F; 537.1 K)
Hazards
Flash point 128.6 °C (263.5 °F; 401.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,1,1-Tris(aminomethyl)ethane (TAME) is an

chelating ligand
, occupying a face of the coordination polyhedron.

Preparation

TAME is synthesized by the Pd/C-catalyzed hydrogenation of 1,1,1-tris(azidomethyl)ethane. Although

salt metathesis using sodium azide. These two steps are:[1]

3 NaN3 + CH3C(CH2OTs)3 → CH3C(CH2N3)3 + 3 NaOTs
3 H2 + CH3C(CH2N3)3 → CH3C(CH2NH2)3 + 3 N2

Complexes of TAME

The tripodal TAME ligand coordinates facially to metal ions. This stereochemical feature has been exploited in the preparation of platinum(IV) cage complexes, e.g., [Pt(tame)2]4+, which is a six coordinate Pt(IV) complex. Platinum in its +4 oxidation state has a d6 configuration and is kinetically inert. For this reason the formation of [Pt(tame)2]4+ is initiated by installing TAME on a platinum(II) precursor. The resulting square planar complex is oxidized with [PtCl6]2− to produce the target Pt(IV) derivatives.[2]

References

  1. ^ L. J. Zompa and J.-P. Anselme, "Catalytic Reduction of 1,1,1 tris(azidomethyl)ethane to 1,1,1 tris(Aminomethyl)ethane" Org. Prep. Proced. lnt, 6, 103 (1974).
  2. doi:10.1039/A901725I
    ..
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