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1,2-Bis(diphenylphosphino)ethane is a bidendate ligand used in coordination chemistry to prepare metal complexes. It is involved in the metal-catalyzed allylic alkylation and decarboxylation of allylic esters. It is also used in 1,3-diene synthesis. Further, it is used in cycloaddition reactions and carbonylation reactions. In addition to this, it is used to prepare bis(dicyclohexylphosphino)ethane by hydrogenation.
Chelating phosphorus ligand.
The complex with NiCl2 catalyzes the coupling of haloaromatic compounds with Grignard reagents: J. Org. Chem., 49, 478 (1984).
The catalyst prepared in situ with Sodium tetrachloropalladate(II) hydrate, 11886, catalyzes the carbonylation of allylic halides at atmospheric pressure: Chem. Lett., 1873 (1989):
Useful replacement for Triphenylphosphine, L02502, in the Staudinger and Mitsunobu reactions, with the advantage of easier separation of the by-product bis(phosphine oxide) due to its higher polarity compared with triphenylphosphine oxide: Tetrahedron Lett., 39, 7787 (1998). Has also been used as an alternative to PPh3 for the halodehydroxylation of alcohols, e.g. in combination with Hexachloroethane, L14297, alkyl chlorides are formed; the phosphine oxide by-product can readily be separated by filtration: Tetrahedron Lett., 42, 2459 (2001).
Afonin, M. Y.; Smolentsev, A. I.; Konchenko, S. N.; Petrov, P. A. Cyanato- and thiocyanato-substituted triangular clusters of molybdenum, [Mo3S4(dppe)3X3]+ (X = NCO-, NCS-; dppe = 1,2-bis(diphenylphosphino)ethane). J. Coord. Chem. 2015, 68 (3), 422-431.
Bloomfield, A. J.; Sheehan, S. W.; Collom, S. L.; Crabtree, R. H.; Anastas, P. T. A heterogeneous water oxidation catalyst from dicobalt octacarbonyl and 1,2-bis(diphenylphosphino)ethane. New J. Chem. 2014, 38 (4), 1540-1545.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory 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.