1,1,1-Tris(aminomethyl)ethane

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1,1,1-Tris(aminomethyl)ethane
1,1,1-Tris(aminomethyl)ethane.svg
Names
Preferred IUPAC name
2-(Aminomethyl)-2-methylpropane-1,3-diamine
Other names
TAME
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.149.897 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • 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
AppearanceColorless 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).
Infobox references

1,1,1-Tris(aminomethyl)ethane (TAME) is an organic compound with the formula CH3C(CH2NH2)3. It is a colorless liquid. It is classified as a polyamine tripodal ligand, i.e., capable of binding to metal ions through three sites and hence is a tridentate chelating ligand, occupying a face of the coordination polyhedron.

Contents

Preparation

TAME is synthesized by the Pd/C-catalyzed hydrogenation of 1,1,1-tris(azidomethyl)ethane. Although azides are potentially explosive, they are excellent and practical source of primary amines. The required tris(azidomethyl)ethane is obtained from the tritosylate by 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]

Related Research Articles

Azide Chemical compound with azide ion or azide group

Azide is the anion with the formula N
3
. It is the conjugate base of hydrazoic acid (HN3). N
3
is a linear anion that is isoelectronic with CO2, NCO, N2O, NO+
2
and NCF. Per valence bond theory, azide can be described by several resonance structures; an important one being . Azide is also a functional group in organic chemistry, RN3.

Scorpionate ligand

The term scorpionate ligand refers to a tridentate ligand which would bind to a metal in a fac manner. The most popular class of scorpionates are the hydrotris(pyrazolyl)borates or Tp ligands. These were also the first to become popular. These ligands first appeared in journals in 1966 from the then little-known DuPont chemist of Ukrainian descent, Swiatoslaw Trofimenko. Trofimenko called this discovery "a new and fertile field of remarkable scope".

Metal ammine complex

In coordination chemistry, metal ammine complexes are metal complexes containing at least one ammonia (NH3) ligand. "Ammine" is spelled this way due to historical reasons; in contrast, alkyl or aryl bearing ligands are spelt with a single "m". Almost all metal ions bind ammonia as a ligand, but the most prevalent examples of ammine complexes are for Cr(III), Co(III), Ni(II), Cu(II) as well as several platinum group metals.

1,4,7-Triazacyclononane Chemical compound

1,4,7-Triazacyclononane, known as "TACN" which is pronounced "tack-en," is an aza-crown ether with the formula (C2H4NH)3. TACN is derived, formally speaking, from cyclononane by replacing three equidistant CH2 groups with NH groups. TACN is one of the oligomers derived from aziridine, C2H4NH. Other members of the series include piperazine, C4H8(NH)2, and the cyclic tetramer 1,4,7,10-tetraazacyclododecane.

Platinum(II) chloride Chemical compound

Platinum(II) chloride is the chemical compound PtCl2. It is an important precursor used in the preparation of other platinum compounds. It exists in two crystalline forms, but the main properties are somewhat similar: dark brown, insoluble in water, diamagnetic, and odorless.

2,2′-Bipyridine Chemical compound

2,2′-Bipyridine (bipy or bpy, pronounced ) is an organic compound with the formula C10H8N2. This colorless solid is an important isomer of the bipyridine family. It is a bidentate chelating ligand, forming complexes with many transition metals. Ruthenium and platinum complexes of bipy exhibit intense luminescence, which may have practical applications.

Potassium tetrachloroplatinate Chemical compound

Potassium tetrachloroplatinate(II) is the chemical compound with the formula K2PtCl4. This reddish orange salt is an important reagent for the preparation of other coordination complexes of platinum. It consists of potassium cations and the square planar dianion PtCl42−. Related salts are also known including Na2PtCl4, which is brown-colored and soluble in alcohols, and quaternary ammonium salts, which are soluble in a broader range of organic solvents.

Diphosphines

Diphosphines, sometimes called bisphosphanes, are organophosphorus compounds most commonly used as bidentate phosphine ligands in inorganic and organometallic chemistry. They are identified by the presence of two phosphino groups linked by a backbone, and are usually chelating. A wide variety of diphosphines have been synthesized with different linkers and R-groups. Alteration of the linker and R-groups alters the electronic and steric properties of the ligands which can result in different coordination geometries and catalytic behavior in homogeneous catalysts.

Triphos Chemical compound

Triphos is the name for certain organophosphorus ligands. They are air-sensitive white solids that function as tridentate ligands in coordination and organometallic chemistry.

Bis(diphenylphosphino)methane Chemical compound

1,1-Bis(diphenylphosphino)methane (dppm), is an organophosphorus compound with the formula CH2(PPh2)2. Dppm, a white, crystalline powder, is used in inorganic and organometallic chemistry as a ligand. It is more specifically a chelating ligand because it is a ligand that can bond to metals with two phosphorus donor atoms. The natural bite angle is 73°.

Tripodal ligand

Tripodal ligands are tri- and tetradentate ligands with C3 symmetry. They are popular in research in the areas of coordination chemistry and homogeneous catalysis. Because the ligands are polydentate, they do not readily dissociate from the metal centre.

Metal amides

Metal amides (systematic name metal azanides) are a class of coordination compounds composed of a metal center with amide ligands of the form NR2. Amide ligands have two electron pairs available for bonding. In principle, they can be terminal or bridging. In these two examples, the dimethylamido ligands are both bridging and terminal:

Metal halides

Metal halides are compounds between metals and halogens. Some, such as sodium chloride are ionic, while others are covalently bonded. Covalently bonded metal halides may be discrete molecules, such as uranium hexafluoride, or they may form polymeric structures, such as palladium chloride.

Nickel(II) nitrite is an inorganic compound with the chemical formula Ni(NO2)2. Anhydrous nickel nitrite was first discovered in 1961 by Cyril Clifford Addison, who allowed gaseous nickel tetracarbonyl to react with dinitrogen tetroxide, yielding a green smoke. Nickel nitrite was the second transition element anhydrous nitrite discovered after silver nitrite.

Spectator ligand

In coordination chemistry, a spectator ligand is a ligand that does not participate in chemical reactions of the complex. Instead, spectator ligands occupy coordination sites. Spectator ligands tend to be of polydentate, such that the M-spectator ensemble is inert kinetically. Although they do not participate in reactions of the metal, spectator ligands influence the reactivity of the metal center to which they are bound. These ligands are sometimes referred to as ancillary ligands.

Transition metal amino acid complexes are a large family of coordination complexes containing the conjugate bases of the amino acids, the 2-aminocarboxylates. Amino acids are prevalent in nature, and all of them function as ligands toward the transition metals. Not included in this article are complexes of the amides and ester derivatives of amino acids. Also excluded are the polyamino acids including the chelating agents EDTA and NTA.

Hexaammineplatinum(IV) chloride Chemical compound

Hexaammineplatinum(IV) chloride is the chemical compound with the formula [Pt(NH3)6]Cl4. It is the chloride salt of the metal ammine complex [Pt(NH3)6]4+. The cation features six ammonia (called ammines in coordination chemistry) ligands attached to the platinum(IV) ion. It is a white, water soluble solid.

Transition metal thioether complex

Transition metal thioether complexes comprise coordination complexes of thioether (R2S) ligands. The inventory is extensive.

Transition metal carboxylate complex

Transition metal carboxylate complexes are coordination complexes with carboxylate (RCO2) ligands. Reflecting the diversity of carboxylic acids, the inventory of metal carboxylates is large. Many are useful commercially, and many have attracted intense scholarly scrutiny. Carboxylates exhibit a variety of coordination modes, most common are κ1- (O-monodentate), κ2 (O,O-bidentate), and bridging.

Transition metal dithiocarbamate complexes

Transition metal dithiocarbamate complexes are coordination complexes containing one or more dithiocarbamate ligand, which are typically abbreviated R2dtc. Many complexes are known. Several homoleptic derivatives have the formula M(R2dtc)n where n = 2 and 3.

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. K. N. Brown; D. C. R. Hockless; A. M. Sargeson (1999). "Synthesis and Electrochemistry of [Pt(tame)2]4+: Crystallographic Analysis of Bis[1,1,1-tris(aminomethyl)ethane-N,N'] Platinum(II) Bis(tetrachlorozincate) Dihydrate". J. Chem. Soc., Dalton Trans. 105: 2171-2176. doi:10.1039/A901725I..