Pentamethyldiethylenetriamine

Details:

PMDTA, formally N,N,N′,N′,N′′-pentamethyldiethylenetriamine, is an organic compound with the formula [Me2NCH2CH2]2NMe (Me is CH3). PMDTA is a basic, bulky, and flexible, tridentate ligand that is a used in organolithium chemistry.
Synthesis
PMDTA is prepared by methylating diethylenetriamine with formaldehyde and formic acid.
[H2N(CH2)2]2NH + 5 CH2O + 5 HCO2H → [Me2NCH2CH2]2NMe + 5 CO2 + 5 H2O
Comparison with diethylenetriamine
Unlike diethylenetriamine, all three amines in PDMTA are tertiary. Both PMDTA and diethylenetriamine are tridentate ligands that form two five-membered chelate rings. The σ-donating properties of the amino groups of diethylenetriamine are greater than that of PMDTA in copper(II) complexes. Both ligands can coordinate metal complexes in arrangements where the three nitrogen centers are co-planar or mutually cis.

【Name】
Pentamethyldiethylenetriamine
【CAS】
3030-47-5
【Synonyms】
1,1,4,7,7-PENTAMETHYLDIETHYLENETRIAMINE
Bis(2-dimethylaminoethyl)methylamine
METHYLBIS(2-DIMETHYLAMINOETHYL)-AMINE
PENTAMETHYLDIETHYLENETRIAMINE
PMDETA
PMDTA
pmdt
1,2-Ethanediamine, N-2-(dimethylamino)ethyl-N,N,N-trimethyl-
1,1,4,7,7-Pentamethyldiethylentriamin
【EINECS】
221-201-1
【Molecular Formula】
C9H23N3
【Molecular Weight】
173.3
【Appearance】
colourless liquid with an amine odour
【mp 】
−20 °C(lit.)
【bp 】
198 °C(lit.)
【density 】
0.83 g/mL at 25 °C(lit.)
【vapor pressure 】
0.23 mm Hg ( 20 °C)
【refractive index 】
n20/D 1.442(lit.)
【Fp 】
128 °F
【Stability:】
Stable. Flammable. Incompatible with strong oxidizing agents, strong acids.
【FreezingPoint 】
<-70℃
【Sensitive 】
Air Sensitive