210169-57-6

Basic information

• Product Name: (S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DM-SEGPHOS
• Synonyms: (S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DM-SEGPHOS;(S)-(-)-5,5μ-Bis(diphenylphosphino)-4,4μ-bi-1,3-benzodioxole;(S)-DM-SEGPHOS(R);(S)-DM-SEGPHOS;(S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole;(S)-(-)-DM-SEGPHOS(regR);(S)-DM-SEGPHOS(R) >=94%;(S)-(-)-DM-SEGPHOS®
• CAS NO: 210169-57-6
• Molecular Formula: C₄₆H₄₄O₄P₂
• Molecular Weight: 722.798
• Mol File: 210169-57-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 256-261 °C
• Boiling Point: 816.9±65.0 °C(Predicted)
• Appearance: off-white to pale yellow/Powder
• CAS DataBase Reference: (S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DM-SEGPHOS(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DM-SEGPHOS(210169-57-6)
• EPA Substance Registry System: (S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DM-SEGPHOS(210169-57-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 210169-57-6(Hazardous Substances Data)

Usage

Description

(S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole, min. 98% (S)-DM-SEGPHOS is a chiral ligand used in various chemical reactions, particularly in asymmetric catalysis. It is characterized by its unique structure, which includes a 1,3-benzodioxole backbone with two phosphino groups attached to it. This structure allows for efficient and selective catalysis in a range of chemical processes.

Uses

Used in Pharmaceutical Industry:
(S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole, min. 98% (S)-DM-SEGPHOS is used as a catalyst for asymmetric hydrogenation of ketones, which is a crucial step in the synthesis of various pharmaceutical compounds. The high enantioselectivity and reactivity of this ligand enable the production of chiral molecules with a single, desired configuration, which is essential for the development of effective and safe drugs.
Used in Chemical Industry:
(S)-(-)-5,5'-Bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole, min. 98% (S)-DM-SEGPHOS is used as a ligand in Takasago Ligands and Complexes for Asymmetric Reactions. These ligands are essential for the development of new and improved catalysts for various chemical processes, including the synthesis of fine chemicals, agrochemicals, and other specialty chemicals. The use of this ligand in asymmetric catalysis can lead to more efficient and environmentally friendly processes, as well as the production of high-quality products with minimal waste.

Reaction

Biaryl bisphosphine ligand with narrow dihedral angle. The DM-SEGPHOS ligand, as the ruthenium complex, gives superior enantioselectivity and diastereoselectivity in the asymmetric hydrogenation of α-substituted-β-ketoesters.? Copper catalyzed enantioselective [3 + 2] cycloaddition as a route to γ–amino ketones and 3-pyrrolidinones. Palladium catalyzed enantioselective addition of malonates to dihydroisoquinolines. Ruthenium catalyzed enantioselective synthesis of β amino acids by hydrogenation. Ruthenium catalyzed asymmetric hydrogenation of 3-quinuclidinone.? Diastereo- and enantioselective ruthenium-catalyzed hydrohydroxyalkylation of 2-silyl-butadienes.