Names | |
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Preferred IUPAC name N1,N1-Bis(2-aminoethyl)ethane-1,2-diamine | |
Other names
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Identifiers | |
3D model (JSmol) | |
1739626 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.021.689 |
EC Number |
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27074 | |
MeSH | Tris(2-aminoethyl)amine |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 2922 |
CompTox Dashboard (EPA) | |
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Properties | |
C6H18N4 | |
Molar mass | 146.238 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) |
Refractive index (nD) | 1.497 [1] |
Thermochemistry | |
Std enthalpy of formation (ΔfH⦵298) | −74.3–−72.9 kJ mol−1 |
Std enthalpy of combustion (ΔcH⦵298) | −4860.6–−4859.2 kJ mol−1 |
Hazards | |
GHS labelling: | |
Danger | |
H301, H310, H314 | |
P280, P302+P350, P305+P351+P338, P310 | |
Flash point | 113 °C (235 °F; 386 K) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
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Safety data sheet (SDS) | fishersci.com |
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). |
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. Tris(2-aminoethyl)amine is commonly abbreviated as tren or TREN. It is used a crosslinking agent in the synthesis of polyimine networks and a tripodal ligand in coordination chemistry.
Tris(2-aminoethyl)amine has been used to prepare molecular capsules and related supramolecular structures. [2] [3] [4]
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. [5] 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. Tren is a common impurity in the more common triethylenetetramine ("trien"). As a trifunctional amine, tren forms a triisocyanate when derivatized with COCl2.
TREN is known to react fast in the presence of (aromatic) aldehydes to form an imine. During this process, water is formed, making it a condensation reaction. Due to this fast and efficient reaction, TREN is commonly used in the preparation of polyimines. [6]
The permethylated derivative of tren has 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. [7]
N,N,N-trimethyltren, N(CH2CH2NHMe)3 is also available. [8]
(H2NCH2CH2)3N, like other polyamines, is corrosive. [9] It causes severe skin burns and eye damage, is harmful if inhaled due to the destruction of respiratory tissues, is toxic if swallowed, and can be fatal in contact with skin. Its median lethal dose is 246 mg/kg, oral (rat), and 117 mg/kg, dermal (rabbit). It is also combustible. [10]
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electron pairs, often through Lewis bases. The nature of metal–ligand bonding can range from covalent to ionic. Furthermore, the metal–ligand bond order can range from one to three. Ligands are viewed as Lewis bases, although rare cases are known to involve Lewis acidic "ligands".
In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.
1,10-Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. The 1,10 refer to the location of the nitrogen atoms that replace CH's in the hydrocarbon called phenanthrene.
In coordination chemistry, a scorpionate ligand is a tridentate (three-donor-site) ligand that binds to a central atom 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".
Salen refers to a tetradentate C2-symmetric ligand synthesized from salicylaldehyde (sal) and ethylenediamine (en). It may also refer to a class of compounds, which are structurally related to the classical salen ligand, primarily bis-Schiff bases. Salen ligands are notable for coordinating a wide range of different metals, which they can often stabilise in various oxidation states. For this reason salen-type compounds are used as metal deactivators. Metal salen complexes also find use as catalysts.
Triethylenetetramine (TETA and trien), also known as trientine (INN) when used medically, is an organic compound with the formula [CH2NHCH2CH2NH2]2. The pure freebase is a colorless oily liquid, but, like many amines, older samples assume a yellowish color due to impurities resulting from air-oxidation. It is soluble in polar solvents. The branched isomer tris(2-aminoethyl)amine and piperazine derivatives may also be present in commercial samples of TETA. The hydrochloride salts are used medically as a treatment for copper toxicity.
8-Hydroxyquinoline is an organic compound derived from the heterocycle quinoline. A colorless solid, its conjugate base is a chelating agent, which is used for the quantitative determination of metal ions.
Tripodal ligands are tri- and tetradentate ligands. 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. Many tripodal ligands have C3 symmetry.
In coordination chemistry, denticity refers to the number of donor groups in a given ligand that bind to the central metal atom in a coordination complex. In many cases, only one atom in the ligand binds to the metal, so the denticity equals one, and the ligand is said to be monodentate. Ligands with more than one bonded atom are called polydentate or multidentate. The denticity of a ligand is described with the Greek letter κ ('kappa'). For example, κ6-EDTA describes an EDTA ligand that coordinates through 6 non-contiguous atoms.
Zinc compounds are chemical compounds containing the element zinc which is a member of the group 12 of the periodic table. The oxidation state of zinc in most compounds is the group oxidation state of +2. Zinc may be classified as a post-transition main group element with zinc(II). Zinc compounds are noteworthy for their nondescript appearance and behavior: they are generally colorless, do not readily engage in redox reactions, and generally adopt symmetrical structures.
Metal bis(trimethylsilyl)amides are coordination complexes composed of a cationic metal M with anionic bis(trimethylsilyl)amide ligands (the −N 2 monovalent anion, or −N 2 monovalent group, and are part of a broader category of 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−. Amido complexes of the parent amido ligand NH2− are rare compared to complexes with diorganylamido ligand, such as dimethylamido. Amide ligands have two electron pairs available for bonding.
Tris(trimethylsilyl)amine is the simplest tris(trialkylsilyl)amine which are having the general formula (R3Si)3N, in which all three hydrogen atoms of the ammonia are replaced by trimethylsilyl groups (-Si(CH3)3). Tris(trimethylsilyl)amine has been for years in the center of scientific interest as a stable intermediate in chemical nitrogen fixation (i. e. the conversion of atmospheric nitrogen N2 into organic substrates under normal conditions).
In chemistry, tetradentate ligands are ligands that bind four donor atoms to a central atom to form a coordination complex. This number of donor atoms that bind is called denticity and is a method of classifying ligands.
Nitrilotriacetonitrile (NTAN) is a precursor for nitrilotriacetic acid, for tris(2-aminoethyl)amine and for the epoxy resin crosslinker aminoethylpiperazine.
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.
A transition metal imidazole complex is a coordination complex that has one or more imidazole ligands. Complexes of imidazole itself are of little practical importance. In contrast, imidazole derivatives, especially histidine, are pervasive ligands in biology where they bind metal cofactors.
Cobalt compounds are chemical compounds formed by cobalt with other elements.
Polyimines are classified as polymer materials that contain imine groups, which are characterised by a double bond between a carbon and nitrogen atom. The term polyimine can also be found occasionally in covalent organic frameworks (COFs). In (older) literature, polyimines are sometimes also referred to as poly(azomethine) or polyschiff.
Transition metal sulfate complexes or sulfato complexes are coordination complexes with one or more sulfate ligands. Sulfate binds to metals through one, two, three, or all four oxygen atoms. Common are complexes where sulfate is unidentate or chelating bidentate. Examples are respectively [Co(tren)(NH3)(SO4)]+ (tren = tris(2-aminoethyl)amine) and Co(phen)2SO4. All four oxygen atoms of sulfate bond to metals in some Dawson-type polyoxometalates, e.g. [S2Mo18O62]4-.