127759-67-5

Basic information

• Product Name: (1R,2R)-BIS[TERT-BUTYL(PHENYL)PHOSPHINO]ETHANE
• Synonyms: (1S,2S)-BIS[TERT-BUTYL(PHENYL)PHOSPHINO]ETHANE;(1R,2R)-BIS[TERT-BUTYL(PHENYL)PHOSPHINO]ETHANE
• CAS NO: 127759-67-5
• Molecular Formula: C₂₂H₃₂P₂
• Molecular Weight: 358.44
• Mol File: 127759-67-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,2R)-BIS[TERT-BUTYL(PHENYL)PHOSPHINO]ETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-BIS[TERT-BUTYL(PHENYL)PHOSPHINO]ETHANE(127759-67-5)
• EPA Substance Registry System: (1R,2R)-BIS[TERT-BUTYL(PHENYL)PHOSPHINO]ETHANE(127759-67-5)

Safety Data

• Hazardous Substances Data: 127759-67-5(Hazardous Substances Data)

Usage

General Description

(1R,2R)-Bis[tert-butyl(phenyl)phosphino]ethane, also known as (R,R)-Ph-BPE, is a chiral diphosphine ligand used in organometallic and coordination chemistry. It consists of two tert-butyl groups and two phenyl groups attached to a central ethane backbone, with phosphorus atoms at the ends of the molecule. (1R,2R)-BIS[TERT-BUTYL(PHENYL)PHOSPHINO]ETHANE acts as a powerful chelating ligand and has been widely used in asymmetric catalysis, particularly in the hydrogenation of various substrates and other organic transformations. Its chiral nature allows for the synthesis of enantioenriched molecules, making it a valuable tool in the field of asymmetric synthesis and chemical research.

Upstream product

• 507-20-0 tertiary butyl chloride 
• 60778-67-8 dilithium salt of 1,2-bis(phenylphosphino)ethane 
• 7377-98-2 (-)-menthyl chloroacetate 
• 677-22-5 tert-butylmagnesium chloride 
• 644-97-3 Dichlorophenylphosphine 

Downstream Products

• 115241-63-9 ethane-1,2-diyibis(phenyl-t-butylphosphine)dioxane 

Relevant articles and documents

Synthesis and reactions of phosphine-boranes. Synthesis of new bidentate ligands with homochiral phosphine centers via optically pure phosphine-boranes

Secondary and tertiary phosphine-boranes were synthesized in one-pot from phosphine oxides or substituted chlorophosphines without isolation of the intermediate phosphines. Phosphine-boranes having a methyl group were metalated with sec-butyllithium. The generated carbanions reacted with alkyl halides or carbonyl compounds to yield various phosphine-borane derivatives. The carbanions underwent copper(II)-promoted oxidative coupling without impairment of the borane functionality. Secondary phosphine-boranes reacted with alkyl halides, aldehydes, or α,β-unsaturated carbonyl compounds to give phosphine-borane derivatives having a functional group. The boranato group of phosphine-boranes was removed in a stereospecific manner with retention of configuration by treatment with a large excess of amine such as morpholine. A new route to bidentate ligands with homochiral phosphine centers has been explored by utilizing these characteristic reactivities of phosphine-boranes. Thus, optically pure (S,S)-1,2-bis(o-anisylphenylphosphino)ethane, (R,R)-1,2-bis(tert-butylphenyl-phosphino)ethane, and (S,S)-1,4-bis(o-anisylphenylphosphino)butane have been synthesized via phosphine-boranes.