660392-16-5

Usage

Uses

Used in Chemical Synthesis Industry:
Phosphinic acid, [[bis(phenylmethyl)amino]methyl]-, ethyl ester is used as a precursor for the production of pesticides and pharmaceuticals, leveraging its reactivity and structural properties to facilitate the synthesis of various compounds.
Used in Catalyst and Stabilizer Applications:
In the chemical industry, Phosphinic acid, [[bis(phenylmethyl)amino]methyl]-, ethyl ester serves as a stabilizer and catalyst in chemical reactions, enhancing the efficiency and selectivity of processes by promoting desired transformations and preventing unwanted side reactions.
Used in Organometallic Chemistry:
Phosphinic acid, [[bis(phenylmethyl)amino]methyl]-, ethyl ester is used as a ligand in organometallic chemistry, where it forms coordination complexes with various metal ions, contributing to the development of new catalysts and materials with unique properties.
Used in Antimicrobial and Pharmacological Research:
Phosphinic acid, [[bis(phenylmethyl)amino]methyl]-, ethyl ester has been studied for its potential antimicrobial properties, suggesting its use in the development of new antimicrobial agents. Additionally, its pharmacological properties are of interest for the discovery of new therapeutic agents, particularly in the context of drug development.
It is crucial to handle Phosphinic acid, [[bis(phenylmethyl)amino]methyl]-, ethyl ester with care due to its potential health and safety risks, ensuring proper management and containment during its use in various applications.

Upstream product

• 64-17-5 ethanol 
• 660392-15-4 (N,N-dibenzylamino)methylphosphonic acid 
• 103-49-1 dibenzylamine 
• 541-41-3 chloroformic acid ethyl ester 

Relevant academic research and scientific papers

Lanthanide Complexes of DO3A-(Dibenzylamino)methylphosphinate: Effect of Protonation of the Dibenzylamino Group on the Water-Exchange Rate and the Binding of Human Serum Albumin

Protonation of a distant, noncoordinated group of metal-based magnetic resonance imaging contrast agents potentially changes their relaxivity. The effect of a positive charge of the drug on the human serum albumin (HSA)-drug interaction remains poorly understood as well. Accordingly, a (dibenzylamino)methylphosphinate derivative of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) was efficiently synthesized using pyridine as the solvent for a Mannich-type reaction of tBu3DO3A, formaldehyde, and Bn2NCH2PO2H2 ethyl ester. The ligand protonation and metal ion (Gd3+, Cu2+, and Zn2+) stability constants were similar to those of the parent DOTA, whereas the basicity of the side-chain amino group of the complexes (logKA = 5.8) was 1 order of magnitude lower than that of the free ligand (log KA = 6.8). The presence of one bound water molecule in both deprotonated and protonated forms of the gadolinium(III) complex was deduced from the solid-state X-ray diffraction data [gadolinium(III) and dysprosium(III)], from the square antiprism/twisted square antiprism (SA/TSA) isomer ratio along the lanthanide series, from the fluorescence data of the europium(III) complex, and from the 17O NMR measurements of the dysprosium(III) and gadolinium(III) complexes. In the gadolinium(III) complex with the deprotonated amino group, water exchange is extremely fast (M = 6 ns at 25 °C), most likely thanks to the high abundance of the TSA isomer and to the presence of a proximate protonable group, which assists the water-exchange process. The interaction between lanthanide(III) complexes and HSA is pH-dependent, and the deprotonated form is bound much more efficaciously (13% and 70% bound complex at pH = 4 and 7, respectively). The relaxivities of the complex and its HSA adduct are also pH-dependent, and the latter is approximately 2-3 times increased at pH = 4-7. The relaxivity for the supramolecular HSA-complex adduct (r1b) is as high as 52 mM-1 s-1 at neutral pH (at 20 MHz and 25 °C). The findings of this study stand as a proof-of-concept, showing the ability to manipulate an albumin-drug interaction, and thus the blood pool residence time of the drug, by introducing a positive charge in a side-chain amino group.

Lanthanide(III) Complexes of Novel Mixed Carboxylic-Phosphorus Acid Derivatives of Diethylenetriamine: A Step towards More Efficient MRI Contrast Agents

Three novel phosphorus-containing analogues of H5DTPA (DTPA = diethylenetriaminepentaacetate) were synthesised (H6L1, H5L2, H5L3). These compounds have a -CH2-P(O)(OH)-R function (R = OH, Ph, CH2NBn2) attached to the central nitrogen atom of the diethylenetriamine backbone. An NMR study reveals that these ligands bind to lanthanide(III) ions in an octadentate fashion through the three nitrogen atoms, a P-O oxygen atom and four carboxylate oxygen atoms. The complexed ligand occurs in several enantiomeric forms due to the chirality of the central nitrogen atom and the phosphorus atom upon coordination. All lanthanide complexes studied have one coordinated water molecule. The residence times (τM 298) of the coordinated water molecules in the gadolinium(III) complexes of H6L1 and H5L2 are 88 and 92 ns, respectively, which are close to the optimum. This is particularly important upon covalent and noncovalent attachment of these Gd3+ chelates to polymers. The relaxivity of the complexes studied is further enhanced by the presence of at least two water molecules in the second coordination sphere of the Gd3+ ion, which are probably bound to the phosphonate/phosphinate moiety by hydrogen bonds. The complex [Gd(L 3)(H2O)]2- shows strong binding ability to HSA, and the adduct has a relaxivity comparable to MS-325 (40 s-1mM -1 at 40MHz, 37°C) even though it has a less favourable τM value (685 ns). Transmetallation experiments with Zn 2+ indicate that the complexes have a kinetic stability that is comparable to-or better than-those of [Gd(dtpa)(H2O)]2- and [Gd(dtpa-bma)(H2O)].