53369-79-2

Usage

Uses

Used in Chemical Synthesis:
N,N,N',N'-Tetramethyl-2,2-dimethyl-1,3-propanediamine is used as a ligand in organometallic chemistry for facilitating various chemical reactions and enhancing the stability and reactivity of metal complexes.
Used in Catalyst Applications:
TMEDA is employed as a catalyst in numerous chemical reactions, particularly in the formation of polymer resins, to accelerate the reaction process and improve the yield of desired products.
Used in Peptide Synthesis:
In peptide synthesis, N,N,N',N'-Tetramethyl-2,2-dimethyl-1,3-propanediamine is used as a scavenger to remove unwanted byproducts and side reactions, thereby improving the purity and efficiency of the synthesis process.
Used in Pharmaceutical Production:
TMEDA is utilized as a component in the production of pharmaceuticals, contributing to the synthesis of various drug molecules and enhancing their therapeutic properties.
Used in Polymerization Stabilization:
N,N,N',N'-Tetramethyl-2,2-dimethyl-1,3-propanediamine is used as a stabilizer in the polymerization of acrylics and vinyl monomers, ensuring the formation of uniform and stable polymer structures.
Used in Research and Development:
TMEDA is also employed in research and development settings for the study of new chemical reactions, the development of novel catalysts, and the exploration of its potential applications in various industries.

Upstream product

• 50-00-0 formaldehyd 
• 7328-91-8 2,2-Dimethyl-1,3-diaminopropane 
• 53369-71-4 N,N,2,2-tetramethyl-1,3-propanediamine 

Relevant academic research and scientific papers

Encapsulation of protonated diamines in a water-soluble, chiral, supramolecular assembly allows for measurement of hydrogen-bond breaking followed by nitrogen inversion/rotation

Amine nitrogen inversion, difficult to observe in aqueous solution, is followed in a chiral, supramolecular host molecule with purely rotational T-symmetry that reduces the local symmetry of encapsulated monoprotonated diamines and enables the observation and quantification of ΔG ? for the combined hydrogen-bond breaking and nitrogen inversion/rotation (NIR) process. Free energies of activation for the combined hydrogen-bond breaking and NIR process inside of the chiral assembly were determined by the NMR coalescence method. Activation parameters for ejection of the protonated amines from the assembly confirm that the NIR process responsible for the coalescence behavior occurs inside of the assembly rather than by a guest ejection/NIR/re-encapsulation mechanism. For one of the diamines, N,N,N′,N′-tetramethylethylenediamine, the relative energy barriers for the hydrogen-bond breaking and NIR process were calculated at the G3(MP2)//B3LYP/6-31++G(d,p) level of theory, and these agreed well with the experimental data.

Selective oxidation of exogenous substrates by a bis-Cu(III) bis-oxide complex: Mechanism and scope

Cu(III)2(μ-O)2 bis-oxides (O) form spontaneously by direct oxygenation of nitrogen-chelated Cu(I) species and constitute a diverse class of versatile 2e?/2H+ oxidants, but while these species have attracted attention as biomimetic models for dinuclear Cu enzymes, reactivity is typically limited to intramolecular ligand oxidation, and systems exhibiting synthetically useful reactivity with exogenous substrates are limited. OTMPD (TMPD = N1, N1, N3, N3-tetramethylpropane-1,3-diamine) presents an exception, readily oxidizing a diverse array of exogenous substrates, including primary alcohols and amines selectively over their secondary counterparts in good yields. Mechanistic and DFT analyses suggest substrate oxidation proceeds through initial axial coordination, followed by rate-limiting rotation to position the substrate in the Cu(III) equatorial plane, whereupon rapid deprotonation and oxidation by net hydride transfer occurs. Together, the results suggest the selectivity and broad substrate scope unique to OTMPD are best attributed to the combination of ligand flexibility, limited steric demands, and ligand oxidative stability. In keeping with the absence of rate-limiting C–H scission, OTMPD exhibits a marked insensitivity to the strength of the substrate Cα–H bond, readily oxidizing benzyl alcohol and 1-octanol at near identical rates.