Tetraethyl methylidenediphosphonate is used in the synthesis of tetrazoloquinoline-based mono- and bisphosphonate esters. It acts as an intermediate for the synthesis of bisphosphonate and bisphosphonic acid derivatives with anticancer and antischistosomal activity. It is also used as a reactant for synthesis of dual substrate-site inhibitors of 3-deoxy-D-arabino-heputosonate 7-phosphate synthase and alpha-amino acid derivatives containing gem-biophosphonates, Lycopene through Wittig-Horner reaction. It is also used as a precursor for the preparation of dendritic polyglycerol anions.
Reacts with aromatic aldehydes to give styrylphosphonates in a two-phase system, no added phase-transfer catalyst being necessary: Synthesis, 396 (1976). For cleavage of the resulting vinyl phosphonates to ɑ-hydroxyaldehydes, see Osmium(VIII) oxide, 12103.
Pachl, P.; Simak, O.; Rezacova, P.; Fabry, M.; Budesínsky, M.; Rosenberg, I.; Brynda, J. Structure-based design of a bisphosphonate 5'(3')-deoxyribonucleotidase inhibitor. Med. Chem. Commun. 2015, 6 (9), 1635-1638.
Faísca Phillips, A. M.; Barros, M. T. Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction. Eur. J. Org. Chem. 2014, 2014 (1), 152-163.
Hazard Statements: H315-H319
Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P280g-P305+P351+P338
Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.