69227-47-0 Usage
Description
TRIS(3,5-DIMETHYLPHENYL)PHOSPHINE is a white to light yellow crystalline powder that serves as a versatile and efficient ligand in various chemical reactions, particularly in the field of asymmetric catalysis.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 69227-47-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,2,2 and 7 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 69227-47:
(7*6)+(6*9)+(5*2)+(4*2)+(3*7)+(2*4)+(1*7)=150
150 % 10 = 0
So 69227-47-0 is a valid CAS Registry Number.
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
69227-47-0Relevant articles and documents
Electrophilic Phosphonium Cation-Mediated Phosphane Oxide Reduction Using Oxalyl Chloride and Hydrogen
Stepen, Arne J.,Bursch, Markus,Grimme, Stefan,Stephan, Douglas W.,Paradies, Jan
supporting information, p. 15253 - 15256 (2018/10/24)
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 %).
A concise synthesis of a new xylyl-biaryl diphosphine ligand for asymmetric hydrogenation of ketones
Henschke, Julian P.,Zanotti-Gerosa, Antonio,Moran, Paul,Harrison, Paul,Mullen, Brendan,Casy, Guy,Lennon, Ian C.
, p. 4379 - 4383 (2007/10/03)
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.
