Tris[2-(MethylaMino)ethyl]aMine is a tripodal polyamine featuring a central tertiary amine core from which three identical 2-(methylamino)ethyl arms radiate outward. This structural arrangement creates a molecule with four nitrogen atoms: one central tertiary amine serving as a branching point and three secondary methylamine groups terminating each flexible ethyl spacer. The C₃-symmetric architecture gives it a pre-organized, claw-like geometry reminiscent of the well-known tris(2-aminoethyl)amine (tren) scaffold, but with N-methyl substituents on each arm. With a predicted pKa of approximately 10.56, the secondary amines exist largely in their protonated form under physiological conditions . This unique tripodal framework equips it with four Lewis base sites capable of forming multidentate coordination complexes, while the methyl substitution modulates steric bulk and electronic character compared to the parent tren system.
Tris[2-(MethylaMino)ethyl]aMine is a versatile research chemical and high-purity building block utilized extensively in coordination chemistry, catalysis, and dendrimer synthesis. The tripodal polyamine architecture of Tris[2-(MethylaMino)ethyl]aMine makes it an exceptional ligand for transition metals, forming stable complexes with copper(II) that serve as precatalysts for water oxidation reactions . In materials science, Tris[2-(MethylaMino)ethyl]aMine reacts rapidly with aromatic aldehydes to form polyimine networks, enabling the preparation of dynamic covalent organic frameworks and self-healing materials . Beyond its coordination applications, Tris[2-(MethylaMino)ethyl]aMine serves as a core moiety for constructing carbohydrate-based dendrimers, where its three secondary amine arms provide attachment points for dendritic wedges containing 21 to 27 monosaccharide residues—structures explored for drug delivery and biomaterial design . Supplied as a liquid with rigorously controlled purity, Tris[2-(MethylaMino)ethyl]aMine offers the reactivity and structural precision required for reproducible organometallic synthesis and supramolecular chemistry.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present.
Immediately call a POISON CENTER/doctor
Hazard Codes (EU)
C (Corrosive)
Risk Statements
R34: Causes burns
Safety Statements
In case of contact with eyes, rinse immediately.
Wear suitable protective clothing, gloves and eye/face protection.
In case of accident or if you feel unwell, seek medical advice immediately
Transport Information
UN 3267 (Corrosive liquid, basic, organic, n.o.s.), Class 8, Packing Group II
GHS Pictograms
GHS05 (Corrosion)
WGK Germany
3 (Significant hazard to water)
Safety & Handling – What You Need to Know
This compound carries multiple hazard classifications:
Hazard Category
Classification
Eye irritation
Category 2 (causes serious eye irritation)
Skin irritation
Category 2 (causes skin irritation)
Skin sensitization
Category 1 (may cause allergic skin reaction)
STOT-SE
Category 3 (may cause respiratory irritation)
Storage class
11 – Combustible solid
Required Protective Measures:
● Eyes: Safety goggles (mandatory).
● Skin: Chemical-resistant gloves (nitrile). If you have a history of skin allergies, take extra precautions due to skin sensitizer classification.
● Respiratory: Use in a fume hood. Avoid breathing dust.
● First aid:
1. Eye contact – rinse with water for 15 min (S26).
2. Skin contact – wash with soap and water. If rash or irritation develops, seek medical advice (skin sensitizer).
3. Inhalation – move to fresh air.
● Storage: Keep container tightly sealed in a dry place at room temperature. Store away from ignition sources (combustible solid). Avoid contact with strong mineral acids (releases irritating free monoester).
● Disposal: Collect as chemical waste. WGK 1 indicates low water hazard, but best practice is not to flush down drains.
Synthetic Route
The synthesis of Tris[2-(MethylaMino)ethyl]aMine can be accomplished through multiple routes. One documented approach involves using tris(2-aminoethyl)amine as the starting material, which is first reacted with ethyl chloroformate in a biphasic water/toluene system to protect the primary amines as carbamates. Subsequent reduction with lithium aluminum hydride in tetrahydrofuran yields the target compound with approximately 80% yield . Alternatively, Tris[2-(MethylaMino)ethyl]aMine can be prepared through direct reaction of tris(2-aminoethyl)amine with methylamine under controlled conditions in methanol at elevated temperatures . Cosperpharm employs validated, scalable synthetic protocols with rigorous purification to ensure ≥97% purity and minimal tren contamination.
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