69227-47-0

Usage

Uses

Used in Chemical Synthesis:
TRIS(3,5-DIMETHYLPHENYL)PHOSPHINE is used as a catalyst for Cu/diphosphine-catalyzed asymmetric hydrogenation of heteroaromatic ketones and enones, enabling the selective synthesis of chiral compounds with high enantioselectivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TRIS(3,5-DIMETHYLPHENYL)PHOSPHINE is used as a catalyst for highly selective rhodium-catalyzed hydrogenation reactions, which are crucial for the production of various pharmaceutical compounds with high purity and enantiomeric excess.
Used in Silicon Stereogenic Compounds Synthesis:
TRIS(3,5-DIMETHYLPHENYL)PHOSPHINE is used for kinetic resolution of donor-functionalized secondary alcohols via Cu-H-catalyzed stereoselective silylation by dehydrogenative Si-O coupling with Si-stereogenic silanes, allowing for the preparation of privileged silicon-stereogenic silanaphthalenes with high selectivity.
Used in Comparative Studies:
In the field of asymmetric catalysis, TRIS(3,5-DIMETHYLPHENYL)PHOSPHINE is used for comparative studies of conformational rigidity of silicon-stereogenic silanes, providing insights into the structure-activity relationships and guiding the design of more efficient catalysts for various applications.

InChI:InChI=1/C24H27P/c1-16-7-17(2)11-22(10-16)25(23-12-18(3)8-19(4)13-23)24-14-20(5)9-21(6)15-24/h7-15H,1-6H3

Upstream product

• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 556-96-7 5-bromo-1,3-xylene 
• 381212-20-0 tris(3,5-dimethylphenyl)phosphine oxide 

Downstream Products

• 551950-92-6 (2S,4S)-2,4-bis[di(3,5-dimethylphenyl)phosphino]pentane 
• 1143504-31-7 nBuP(3,5-xylyl)2 
• 1239667-46-9 ((3,5-Me₂C₆H₃)3P)B(p-C₆F₄H)3 
• 1613373-11-7 C₈⁽¹³⁾CH₁₅BO₂ 
• 1613373-12-8 C₁₆⁽¹³⁾CH₃₀B₂O₂ 
• 74744-62-0 1,1:3,3-bis(1,5-cyclooctandiyl)diboroxane 
• 74289-57-9 bis-(3,5-dimethylphenyl)chlorophosphine 
• 1241384-75-7 1-tert-butoxy-3-(bis(3,5-dimethylphenyl)phosphino)isoquinoline 

Relevant academic research and scientific papers

Electrophilic Phosphonium Cation-Mediated Phosphane Oxide Reduction Using Oxalyl Chloride and Hydrogen

The metal-free reduction of phosphane oxides with molecular hydrogen (H2) using oxalyl chloride as activating agent was achieved. Quantum-mechanical investigations support the heterolytic splitting of H2 by the in situ formed electrophilic phosphonium cation (EPC) and phosphane oxide and subsequent barrierless conversion to the phosphane and HCl. The reaction can also be catalyzed by the frustrated Lewis pair (FLP) consisting of B(2,6-F2C6H3)3 and 2,6-lutidine or phosphane oxide as Lewis base. This novel reduction was demonstrated for triaryl and diaryl phosphane oxides providing access to phosphanes in good to excellent yields (51–93 %).

Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation

Chiral diphosphine ligands analogous to bdpp have been synthesized and tested in order to study the effect of the electronic nature of the ligands in Rh-catalyzed asymmetric hydrogenation of some prochiral olefins. The results are compared with those obtained with the analogous unsubstituted ligand (bdpp). The rhodium-catalyzed asymmetric hydrogenation of olefins was influenced by ligand-based electronic effects, as well as substrate based ones. Excellent ee's (up to 98.3%) have been obtained in the rhodium-catalyzed hydrogenation of (Z)-α-acetamidocinnamic acids and esters.

A concise synthesis of a new xylyl-biaryl diphosphine ligand for asymmetric hydrogenation of ketones

A concise synthesis of a symmetrical biaryl diphosphine ligand bearing 3,5-dimethylphenyl substituents at phosphorus is described. The ruthenium catalysts [diphosphine RuCl2 diamine] containing the new ligand Xyl-TetraPHEMP were found to be as active and as selective as the state-of-the-art catalysts for homogeneous asymmetric ketone hydrogenation.

Anodic Bahavior of Crowded Triarylphosphines. ESR Study of Triarylphosphoniumyl Radicals, Ar3P.+

A large number of triarylphosphines exhibiting different steric hindrance has been prepared.The pyramidalization angle α of these compounds was calculated with use of the MM2 force field and was shown to depend almost exclusively on the number of ortho substituents on the phenyl rings.In a series of isosteric (same α) phosphines, the oxidation potential correlates with the sum of the ?+ Hammett parameters of the phenyl substituents.In the absence of oxygen, anodic oxidation of all the triarylphosphines bearing two o-methyl substituents on each phenyl ring is reversible and yields very persistent phosphoniumyl radicals.These radicals are easly detected by ESR in liquid solution and were shown to retain a pyramidal geometry that is significantly flattened compared to that of the parent phosphine.