Trisamine is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 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.

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. 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

Tris(2-chloroethyl)amine

Trisamine is the organic compound with the formula N3. Often abbreviated HN3, it is a powerful blister agent and a nitrogen mustard gas used for chemical warfare. HN3 was the last of the nitrogen mustard agents developed...

.

The tripodal ligand of greatest commercial significance is nitrilotriacetate

Nitrilotriacetic acid

Nitrilotriacetic acid , C6H9NO6, is a polyamino carboxylic acid and is used as a chelating agent which forms coordination compounds with metal ions such as Ca2+, Cu2+ or Fe3+.The uses of NTA are similar to that of EDTA...

, N(CH₂CO₂^-)₃.

Organic chemistry

Tren is a common impurity in the more common triethylenetetramine ("trien"). As a trifunctional amine, tren forms a triisocyanate

Isocyanate

Isocyanate is the functional group of elements –N=C=O , not to be confused with the cyanate functional group which is arranged as –O–C≡N or with isocyanide, R-N≡C. Any organic compound which contains an isocyanate group may also be referred to in brief as an isocyanate. An isocyanate may have more...

 when derivatized with COCl₂

Phosgene

Phosgene is the chemical compound with the formula COCl2. This colorless gas gained infamy as a chemical weapon during World War I. It is also a valued industrial reagent and building block in synthesis of pharmaceuticals and other organic compounds. In low concentrations, its odor resembles...

.

Safety considerations

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