795290-34-5

Basic information

• Product Name: (1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl
• Synonyms: (1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl;(1S,1μS,2R,2μR)-DuanPhos;(1S,1'S,2R,2'R)-2,2'-bis(1,1-diMethylethyl)-2,2',3,3'-tetrahydro-,1,1'-Bi-1H-isophosphindole;(1S,1'S,2R,2'R)-2,2'-Bis(1,1-dimethylethyl)-2,2',3,3'-tetrahydro-1,1'-bi-1H-isophosphindole,99%e.e.
• CAS NO: 795290-34-5
• Molecular Formula: C24H32P2
• Molecular Weight: 382.465
• Mol File: 795290-34-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 215-226 °C
• Boiling Point: 474.5±45.0 °C(Predicted)
• Appearance: /
• CAS DataBase Reference: (1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl(795290-34-5)
• EPA Substance Registry System: (1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl(795290-34-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 795290-34-5(Hazardous Substances Data)

Usage

Description

(1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl is a chiral phosphine ligand with a unique structure that features a di-tert-butyl substitution and a tetrahydro-1H,1μH(1,1μ)biisophosphindolyl backbone. This complex molecule is characterized by its stereochemistry, with the specific configuration (1S,1μS,2R,2μR), which is crucial for its applications in asymmetric catalysis.

Uses

Used in Asymmetric Hydrogenation:
(1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl is used as a ligand in rhodium-catalyzed ketone hydroacylation, a process that is part of asymmetric hydrogenation. This application is significant because it allows for the selective reduction of ketones to form chiral alcohols, which are essential building blocks in the synthesis of pharmaceuticals and agrochemicals.
Used in Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions:
In the field of organic chemistry, this chiral ligand also serves as a cocatalyst for highly selective rhodium-catalyzed conjugate addition reactions of 4-oxobutenamides with arylboronic acids. This application is valuable for the synthesis of complex organic molecules with high enantioselectivity and regioselectivity, which is crucial for the development of new drugs and advanced materials.
Overall, (1S,1μS,2R,2μR)-2,2μ-Di-tert-butyl-2,3,2μ,3μ-tetrahydro-1H,1μH(1,1μ)biisophosphindolyl is a versatile chiral ligand that plays a critical role in asymmetric catalysis, enabling the production of enantiomerically pure compounds for various applications in the pharmaceutical, agrochemical, and materials science industries.