99665-68-6

Basic information

• Product Name: BIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE
• Synonyms: DI-(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE;BIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE;Bis(4-trifluoromethylphenyl)phosphine,98%;Bis(4-trifluoromethylphenyl)phosphine 97%
• CAS NO: 99665-68-6
• Molecular Formula: C₁₄H₉F₆P
• Molecular Weight: 322.19
• Mol File: 99665-68-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 291.4 °C at 760 mmHg
• Flash Point: 130 °C
• Appearance: /
• Density: 1.317 g/mL at 25 °C
• Refractive Index: n20/D1.512
• CAS DataBase Reference: BIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE(99665-68-6)
• EPA Substance Registry System: BIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE(99665-68-6)

Safety Data

• Hazard Codes: T
• Statements: 25-37-41
• Safety Statements: 26-39-45
• RIDADR: UN 2810 6.1 / PGIII
• Hazardous Substances Data: 99665-68-6(Hazardous Substances Data)

Usage

Description

Bis(4-trifluoromethylphenyl)phosphine is an organophosphorus compound characterized by its phosphorus atom bonded to two 4-trifluoromethylphenyl groups. It is known for its unique electronic properties and stability, making it a versatile building block in various chemical applications.

Uses

Used in Catalyst Preparation:
Bis(4-trifluoromethylphenyl)phosphine is used as a reactant for the preparation of iron(II) chiral diimine diphosphine complexes, which serve as catalysts in asymmetric transfer hydrogenation of ketones. This application is crucial for the synthesis of enantiomerically pure alcohols, which are essential in the pharmaceutical industry.
Used in Enantioselective Reactions:
In the field of enantioselective synthesis, Bis(4-trifluoromethylphenyl)phosphine is utilized as a key component in the development of catalysts for enantioselective decarboxylative allylation and ring-closing metathesis reactions. These reactions are vital for constructing complex molecular architectures with high enantiomeric purity, which is particularly important in the production of biologically active compounds and pharmaceuticals.
Used in Chemical Research:
Bis(4-trifluoromethylphenyl)phosphine is also employed in chemical research as a ligand or a precursor for the synthesis of novel organophosphorus compounds. Its unique properties allow for the exploration of new reaction pathways and the development of innovative synthetic methods, further expanding the scope of organic chemistry.

Upstream product

• 141868-69-1 Benzyl-bis-(4-trifluoromethyl-phenyl)-phosphane 
• 2786-01-8 (4-trifluoromethylphenyl)lithium 
• 15929-43-8 bis(4-(trifluoromethyl)phenyl)phosphine oxide 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 

Downstream Products

• 944836-22-0 (S)-2-(2-(bis(4-trifluoromethyl-phenyl)-phosphino))-5-(4-trifluoromethyl-phenyl)-4-tert-butyl-4,5-dihydro-oxazole 
• 1073641-72-1 trans-1,2-ethenediylbis[di(4-trifluoromethylphenyl)phosphine] 
• 1163249-49-7 (3-ethoxypropyl)bis[4-(trifluoromethyl)phenyl]phosphine 
• 1163249-50-0 [3-(dimethylamino)propyl]bis[4-(trifluoromethyl)phenyl]phosphine 
• 1163249-48-6 (2-ethoxyethyl)bis[4-(trifluoromethyl)phenyl]phosphine 
• 1229618-93-2 C₇₂H₅₈B₄F₂₄P₄ 
• 1006708-91-3 (R)-(p-CF₃)₃-t-BuPHOX 
• 1315513-21-3 (CF₃C₆H₄)2PCH₂CH(OCH₂CH₃)2 
• 1357268-46-2 tetraphenylphosphonium bis(p-trifluoromethylphenyl)dithiophosphinate 
• 1357268-47-3 C₁₄H₉F₆PS₂*H₃N 
• 1122052-40-7 bis(p-trifluoromethylphenyl)dithiophosphinic acid 
• 1426142-02-0 [Cp*Ru(η⁶-C₆H₅P(p-C₆H₄CF₃)₂)][OTf] 
• 1615244-31-9 C₃₈H₂₉F₁₂P₃ 

Relevant articles and documents

A versatile synthesis of chiral β-aminophosphines

A method for the preparation of chiral β-aminophosphines having substituted P-aryl groups is described. Ring-opening of cyclic sulfamidates with metal diarylphosphinites yields β-aminophosphine oxides, which are then reduced to the corresponding phosphines. Effects of the diarylphosphinite countercation on the regioselectivity of the ring-opening reaction (P- versus O-alkylation) are discussed. This method enables the introduction of electron-deficient, electron-rich and sterically hindered diarylphosphino groups, as demonstrated by the synthesis of a series of novel, P-aryl-substituted β-aminophosphines derived from tert-leucinol, valinol and phenylglycinol. Access to these derivatives will create new opportunities for steric and electronic tuning of β-aminophosphine-derived chiral ligands and organocatalysts.

Rhodium catalyzed C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates and analogs

The C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates with aryl boronic acids catalyzed by a rhodium complex was studied with a "conjugate addition/β-C cleavage/protonation" strategy.

Metal-Free Reduction of Phosphine Oxides, Sulfoxides, and N-Oxides with Hydrosilanes using a Borinic Acid Precatalyst

The general reduction of phosphine oxides, sulfoxides, and amine N-oxides was achieved by combining bis(2-chlorophenyl)borinic acid with phenylsilane. The reaction was shown to tolerate a wide range of substrates and could be performed under mild conditions, with only 2.5 mol % of the easily synthesized catalyst. Mechanistic investigations pointed to a key borohydride as the real catalyst and at bis(2-chlorophenyl)borinic acid as a precatalyst.