142421-57-6

Basic information

• Product Name: BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE
• Synonyms: BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE;BIS[BIS(3,5-TRIFLUOROMETHYL)PHENYL]CHLOROPHOSPHINE;Chlorobis[3,5-bis(trifluoromethyl)phenyl]phosphine, 98+%;Chlorobis[3,5-bis(trifluoromethyl)phenyl]phosphine;Chlorobis[3,5-bis(trifluoromethyl)phenyl]phosphine, 98+%, may contain suspended dimethylamine hydrochloride crystals;Bis(3,5-di(trifluoroMethyl)phenyl)chlorophosphine,Min.98%;P,P-Bis[3,5-bis(trifluoromethyl)phenyl]phosphinous chloride;bis[3,5-bis(trifluoromethyl)phenyl]-chlorophosphane
• CAS NO: 142421-57-6
• Molecular Formula: C₁₆H₆ClF₁₂P
• Molecular Weight: 492.63
• Product Categories: Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors;organophosphine ligand;Achiral Phosphine;Aryl Phosphine;P-Cl
• Mol File: 142421-57-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 25-29 °C
• Boiling Point: 333.2°Cat760mmHg
• Flash Point: 155.3°C
• Appearance: colorless/liquid
• Density: g/cm³
• Vapor Pressure: 0.000269mmHg at 25°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE(142421-57-6)
• EPA Substance Registry System: BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE(142421-57-6)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN3265
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 142421-57-6(Hazardous Substances Data)

Usage

Description

BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE, also known as Chlorobis[3,5-bis(trifluoromethyl)phenyl]phosphine, is an organophosphorus compound with a chlorinated phosphorus center and two trifluoromethyl-substituted phenyl groups. It is a versatile reagent in the field of organic chemistry, particularly in catalysis and the synthesis of various ligands.

Uses

Used in Chemical Synthesis:
BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE is used as a reactant for the synthesis of chiral phosphine-aminophosphine ligands for rhodium-catalyzed asymmetric hydrogenation. These ligands are crucial in enhancing the selectivity and efficiency of hydrogenation reactions, which are widely used in the pharmaceutical and fine chemicals industries.
Used in Palladium-Catalyzed Reactions:
In the field of homogeneous catalysis, BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE is used as a ligand for palladium-catalyzed stereoselective allylation reactions. These reactions are essential in the construction of complex molecular structures with high enantiomeric purity, which are often required in the synthesis of biologically active compounds and pharmaceuticals.
Used in Enantioselective Hydrogenations:
BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE is also employed as a ligand in enantioselective hydrogenations, a class of reactions that are vital in the production of optically active compounds. These reactions are widely used in the synthesis of chiral drugs, agrochemicals, and other specialty chemicals.
Used as a Josiphos Analog:
In asymmetric hydrogenation, BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE serves as a Josiphos analog, a type of ligand that is known for its high enantioselectivity and reactivity in various hydrogenation reactions. This makes it a valuable tool in the development of new catalytic systems for asymmetric hydrogenations.
Used in Asymmetric Hydrovinylation Reactions:
BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE is used as a ligand in asymmetric hydrovinylation reactions, which are important for the synthesis of vinylsilanes and other vinylmetal compounds with high enantiomeric purity. These compounds are valuable building blocks in the preparation of complex organic molecules and have applications in the pharmaceutical, agrochemical, and materials science industries.

InChI:InChI=1/C16H6ClF12P/c17-30(11-3-7(13(18,19)20)1-8(4-11)14(21,22)23)12-5-9(15(24,25)26)2-10(6-12)16(27,28)29/h1-6H

Upstream product

• 1069-08-5 diethylphosphoramidous dichloride 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 112981-69-8 3,5-bis(trifluoromethyl)phenylmagnesium bromide 
• 159418-71-0 [di-3,5-bis(trifluoromethyl)phenyl](diethyl-amino)phosphine 
• 15979-14-3 bis[3,5-bis(trifluoromethyl) phenyl]phosphine oxide 

Downstream Products

• 1092491-37-6 (S)-4-tert-butyl-2-(2-(bis(3,5-bis(trifluoromethyl)phenyl)phosphino)phenyl)-4,5-dihydrooxazole 

Relevant articles and documents

Catalytic Dehydrocoupling of Amine-Boranes using Cationic Zirconium(IV)-Phosphine Frustrated Lewis Pairs

A series of novel, intramolecular Zr(IV)/P frustrated Lewis pairs (FLPs) based on cationic zirconocene fragments with a variety of ancillary cyclopentadienyl and 2-phosphinoaryloxide (-O(C6H4)PR2, R = tBu and 3,5-CF3-(C6H3)) ligands are reported and their activity as catalysts for the dehydrocoupling of dimethylamine-borane (Me2NH·BH3) assessed. The FLP system [(C9H7)2ZrO(C6H4)PtBu2][B(C6F5)4] is shown to give unprecedented turnover frequencies (TOF) for a catalyst based on a group 4 metal (TOF ≥ 600 h-1), while also proving to be the most efficient FLP catalyst reported to date. The mechanism of this reaction has been probed using analogous intermolecular Zr(IV)/P FLPs, permitting deconvolution of the reactions taking place at both the Lewis acidic and basic sites. Elucidation of this mechanism revealed an interesting cooperative two-cycle process where one cycle is FLP mediated and the other, a redistribution of a linear diborazane intermediate, relies solely on the presence of a Zr(IV) Lewis acid.

Systematic Study of the Stereoelectronic Properties of Trifluoromethylated Triarylphosphines and the Correlation of their Behaviour as Ligands in the Rh-Catalysed Hydroformylation

The stereoelectronic properties of a series of trifluoromethylated aromatic phosphines have been studied using different approaches. The σ-donating capability has been evaluated by nuclear magnetic resonance (NMR) spectroscopy of the selenide derivatives and the protonated form of the different trifluoromethylated phosphines. The coupling constants between phosphorous and selenium (1JSeP) and phosphorous and hydrogen (1JHP) can be predicted by empirical equations and correlate the basicity of the phosphines with the number and relative position of trifluoromethyl groups. In contrast, the π-acceptor character of the ligands has been evaluated by measuring the frequency of the CO vibration in the infrared (IR) spectra of the corresponding Vaska type iridium complexes ([IrCl(CO)(PAr3)2], PAr3=triarylphosphine). Moreover, the correlation between the electronic properties and the performance of these phosphines as ligands in the rhodium-catalysed hydroformylation of 1-octene has been established. Phosphines with the lowest basicity, that are those with the highest number of trifluoromethyl groups, gave rise to more active catalytic systems.

Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.