DIMETHYLPHOSPHINE OXIDE

Description

Dimethylphosphine oxide is an organophosphorus compound. It can be used for the preparation of triacrylphosphine oxide. It can be used as an asymmetric catalyst. In addition, it can be used for the preparation of alkenyldiphenylphosphine oxides, and Horner-Witting reagents. In addition, it is also a kind of capping ligand in organic chemistry.

Chemical Properties

Dimethylphosphine oxide is a colorless liquid that soluble in polar organic solvents.It exists as the phosphine oxide, not the hydroxy tautomer.

Uses

Dimethylphosphine Oxide is used in preparation of substituted piperazine derivatives as DGKα/DGKζ inhibitors for the treatment of viral infections and cancer. It is also used as an organic synthetic raw material for the preparation of (α-aminoalkyl)dimethylphosphine oxide enantiomers. Asymmetric synthesis of α-amino-α-polyfluoroalkyl dimethylphosphine oxides was accomplished through diastereoselective addition of dimethylphosphine oxide to enantiomeric Ellman's aldimines, RFCH=NS(O)tert-Bu (RF=CF3, CHF2, PhCF2).

Application

Dimethylphosphine oxide (DMPO) is a hydrogen bonding receptor that can be used to prepare ALK inhibitor compounds (WX-0593) containing DMPO molecules.  The results of enzyme assay experiments showed that WX-0593 has high activity against wild-type and mutant ALK, and also inhibits ROS1WT in Ba/F3 cell line very well.  In addition, WX-0593 is currently undergoing a phase I/II trial in ALK-positive NSCLC and is expected to be used for the treatment of ROS1-positive NSCLC.

Reactions

Chlorination gives dimethylphosphoryl chloride. It undergoes hydroxymethylation with formaldehyde. Me2P(O)H+CH2O→Me2P(O)CH2OH Many aldehydes effect a similar reaction.

References

https://en.wikipedia.org/wiki/Dimethylphosphine_oxide
http://www.sigmaaldrich.com/catalog/product/aldrich/287881?lang=en&region=US
Ganesan, Paramasivam, and S. Lakshmipathi. "Impact of heterogeneous passivation of trimethylphosphine oxide and di-methylphosphine oxide surface ligands on the electronic structure of Cd n Se n, (n =6, 15) quantum dots: A DFT study." Physica E: Low-dimensional Systems and Nanostructures 83(2016):284-296.