(S,S)-2,3-Bis(diphenylphosphino)butane, CAS No. 64896-28-2

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64896-28-2

Catalog No. EBD54298

CAS 64896-28-2

Name (S,S)-2,3-Bis(diphenylphosphino)butane

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Basic Information

Synonyms: (S,S)-2,3-Bis(diphenylphosphino)butane (2S,3S)-(?)-Bis(diphenylphosphino)butane (2S,3S)-Butane-2,3-diylbis(diphenylphosphine) (S,S)-Chiraphos (2S,3S)-(-)-Bis(diphenylphosphino)butane(S,S)-CHIRAPHOS (2S,3S)-butane-2,3-diylbis(diphenylphosphane) (2S,3S)-(-)-Bis(diphenylphosphino)butane (2S,3S)-(?)-2,3-Bis(diphenylphosphino)butane chiraphos (-)-chiraphos (2s,3s)-chiraphos (s,s)-(-)-chiraphos 2s,3s-bis(diphenylphosphino)butane (2s,3s)-2,3-bis(diphenylphosphino)butane (2s,3s)-(-)-2,3-bis(diphenylphosphino)butane [s-(r*,r*)]-2,3-bis(diphenylphosphino)butane [(1s,2s)-1,2-dimethyl-1,2-ethanediyl]bis[diphenylphosphine] (s,s)-(-)-(1,2-dimethyl-1,2-ethanediyl)bis(diphenylphosphine)

Molecular Formula: C28H28P2

Molecular Weight: 426.47

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands Synthetic Chemistry > Catalysts and Ligands > Phosphorus Ligands

Product Description:

(2S,3S)-(-)-Bis(diphenylphosphino)butane, commonly abbreviated as (S,S)-Chiraphos, is a chiral bidentate phosphine ligand. It is a white to off-white crystalline solid with the molecular formula C28H28P2. The compound features a C2-symmetric backbone derived from 2,3-butanediol, with two diphenylphosphino groups attached to the chiral carbon centers. Its primary and most significant application is in asymmetric catalysis as a chiral ligand. (S,S)-Chiraphos is particularly effective in coordinating with transition metals such as rhodium and ruthenium to form highly enantioselective catalysts. These catalysts are widely employed in hydrogenation reactions, especially for the asymmetric hydrogenation of dehydroamino acid derivatives and enamides to produce enantiomerically pure α-amino acids, which are crucial building blocks in pharmaceutical synthesis. Due to its well-defined chiral environment and strong chelating ability, (S,S)-Chiraphos has been a benchmark ligand in the development of homogeneous asymmetric hydrogenation processes. It is a specialized reagent primarily used in academic and industrial research focused on enantioselective synthesis, rather than a commodity chemical or a product with a direct end-use in materials or life sciences.

Physical Properties

Melting Point: 108-110 °C(lit.)

Boiling Point: 529.19 °C at 760 mmHg

Flash Point: 291.15 °C

Analytical Data

Appearance: White granular powder