Tetraethyl [(dimethylamino)methylene]bisphosphonate

CAS 18855-52-2, Cat. No EN300-18532769

Reagent for homologous acid synthesis

Tetraethyl dimethylaminomethylenediphosphonate is a useful reagent for synthesizing aryl- and heteroaryl-acetic acids from aldehydes via carbon chain extension¹. It forms a stable enamine phosphonate intermediate that hydrolyzes under acidic conditions to yield the corresponding acid. The method is effective for substrates like benzothiophene, thiophene, and furan derivatives. It offers a mild, high-yielding (up to 90%) and scalable alternative to traditional homologation reactions. The reagent is bench-stable and easy to handle, making it suitable for academic and industrial applications.

Synonyms: tetraethyl dimethylaminomethylenediphosphonate; tetraethyl [(dimethylamino)methylene]bisphosphonate; 1,1-bis(diethoxyphosphoryl)-N,N-dimethylmethanamine; phosphonic acid, [(dimethylamino)methylene]bis-, tetraethyl ester; phosphonic acid, P,P'-[(dimethylamino)methylene]bis-, P,P,P',P'-tetraethyl ester; diethyl [(diethoxyphosphoryl)(dimethylamino)methyl]phosphonate

Selected publication

1. Use of Tetraethyl Dimethylaminomethylenediphosphonate in the Synthesis of Benzothiophene-2-Acetic Acid and Other Carboxylic Acids.Degenhardt, C. R. Synth Commun 1982, 12 (6), 415–421. DOI: 10.1080/00397918208065945