66470-81-3

Usage

Uses

Used in Chemical Industry:
TRIS(1,1,1,3,3,3-HEXAFLUORO-2-PROPYL) PHOSPHITE is used as a catalyst for the hydroformylation of olefins in combination with a rhodium complex. Its unique steric and electronic properties enable it to improve the efficiency and selectivity of the hydroformylation process, which is crucial for the production of various chemicals and pharmaceuticals.
Used in Nucleoside Chemistry:
TRIS(1,1,1,3,3,3-HEXAFLUORO-2-PROPYL) PHOSPHITE is used as a reagent in the formation of deoxyribonucleoside 3′-bis(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite units when reacting with nucleosides. This application is significant for the development of novel nucleic acid derivatives and potential therapeutic agents in the field of molecular biology and drug discovery.

InChI:InChI=1/C9H3F18O3P/c10-4(11,12)1(5(13,14)15)28-31(29-2(6(16,17)18)7(19,20)21)30-3(8(22,23)24)9(25,26)27/h1-3H

Upstream product

• 6919-74-0 sodium 1-trifluoromethyl-2,2,2-trifluoroethoxide 
• 120104-57-6 bis(1,1,1,3,3,3-hexafluoropropan-2-yl) hydrogen phosphite 
• 121-44-8 triethylamine 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 

Downstream Products

• 133519-14-9 Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester bis-(2,2,2-trifluoro-1-trifluoromethyl-ethyl) ester 
• 157794-99-5 tetrakis(hexafluoroisopropoxy)-α-chlorobenzylphosphorane 
• 120942-91-8 Phosphorous acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester bis-(2,2,2-trifluoro-1-trifluoromethyl-ethyl) ester 
• 120942-89-4 Phosphorous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2,2,2-trifluoro-1-trifluoromethyl-ethyl) ester 
• 130288-81-2 5'-O-dimethoxytrityl-2'-deoxythymidine-3'-H-phosphonate 
• 120942-90-7 Phosphorous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-dibenzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester bis-(2,2,2-trifluoro-1-trifluoromethyl-ethyl) ester 
• 85762-87-4 Tetrakis(1,1,1,3,3,3-hexafluoroisopropoxy)(phenylthio)phosphorane 
• 120942-92-9 Phosphorous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester bis-(2,2,2-trifluoro-1-trifluoromethyl-ethyl) ester 

Relevant academic research and scientific papers

Silver-Catalyzed Regioselective Phosphorylation of para-Quinone Methides with P(III)-Nucleophiles

A simple and efficient method for the silver-catalyzed regioselective phosphorylation of para-quinone methides (p-QMs) with P(III)-nucleophiles (P(OR)3, ArP(OR)2, Ar2P-OR) has been established via Michaelis-Arbuzov-type reaction. A broad range of P(III)-nucleophiles and para-quinone methides are well tolerated under the mild conditions, giving the expected diarylmethyl-substituted organophosphorus compounds with good to excellent yields. Moreover, a series of corresponding enantiomers can be obtained by employing dialkyl arylphosphonite (ArP(OR)2) as substrates. The control experiments and 31P NMR tracking experiments were also performed to gain insights for the plausible reaction mechanism. This protocol may have significant implications for the formation of C(sp3)-P bonds in Michaelis-Arbuzov-type reactions.

Filling a Niche in “Ligand Space” with Bulky, Electron-Poor Phosphorus(III) Alkoxides

The chemistry of phosphorus(III) ligands, which are of key importance in coordination chemistry, organometallic chemistry and catalysis, is dominated by relatively electron-rich species. Many of the electron-poor PIII ligands that are readily available have relatively small steric profiles. As such, there is a significant gap in “ligand space” where more sterically bulky, electron-poor PIII ligands are needed. This contribution discusses the coordination chemistry, steric and electronic properties of PIII ligands bearing highly fluorinated alkoxide groups of the general form PRn(ORF)3?n, where R=Ph, RF=C(H)(CF3)2 and C(CF3)3; n=1–3. These ligands are simple to synthesize and a range of experimental and theoretical methods suggest that their steric and electronic properties can be “tuned” by modification of their substituents, making them excellent candidates for large, electron-poor ligands.

DISPROPORTIONATION OF BIS(FLUOROALKYL) HYDROGEN PHOSPHITES TO TRIS(FLUOROALKYL) PHOSPHITES UNDER THE ACTION OF BASES

Bis(fluoroalkyl) hydrogen phosphites formed by the reaction of PCl3 with fluorinated alcohols in the presence of water undergo disproportionation under the action of triethylamine to form tris(fluoroalkyl) phosphites and triethylammonium fluoroalkyl hydrogen phosphites.The reaction mechanism is discussed.

SYNTHESIS OF TETRAKIS(HEXAFLUOROISOPROPOXY)CHLOROPHOSPHORANE

By phosphorylating hexafluoro-2-propanol with phosphorus pentachloride and with tris(hexafluoroisopropoxy)dichlorophosphorane in the absence of a base stable tetrakis(hexafluoroisopropoxy)chlorophosphorane was prepared for the first time; its reactions wi

USE OF NEW PHOSPHONYLATING AND COUPLING AGENTS IN THE SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES VIA THE H-PHOSPHONATE APPROACH

Tris(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite was used as a phosphonylating reagent for the preparation of nucleoside 3'-H-phosphonate units.The use of a new coupling reagent, 1,3-dimethyl-2-chloro-imidazolinium chloride (DMCI) for the internucleotidic H-phosphonate bond formation via the H-phosphonate approach is also discussed in detail.

Preparation and Nuclear Magnetic Resonance Studies of Pentacoordinated Phosphorus Compounds Containing Hexafluoroisopropoxy Groups

The reaction of 1,1,1,3,3,3-hexafluoroisopropyl benzenesulfenate (7) with tris(1,1,1,3,3,3-hexafluoroisopropyl)phosphite (8) yielded tetrakis(1,1,1,3,3,3-hexafluoroisopropoxy)(phenylthio)phosphorane (9).Variable-temperature 19F NMR studies of 9 show that

On the mechanism of the nickel-catalysed regioselective cyclodimerization of isoprene

A study of various Ni-ligand catalysed oligomerizations of isoprene has shown that with π-acidic P ligands the selectivity to cyclodimers amount to 97%. A new type of ligand is introduced, viz. fluoroalkyl phosphites having π-acceptor properties comparable to those of, e.g. PCl3. With tris(hexafluoroisopropyl) phosphite the main product is 1,4-dimethy1-4-vinylcyclohexene. A detailed explanation based on a two-step mechanism is given. As to the first step, for a series of ligands having similar steric properties the changes in product distribution as a function of the electronic ligand parameter are explained in terms of a gradual change in HOMO-LUMO interactions between Ni and the olefins, with strong π-acidic ligands promoting the head-to-head coupling of the isoprene molecules. The second step, involving reductive elimination of a cyclodimer from the metal, shows an increasing selectivity towards substituted cyclohexenes for the head-to-head and tail-to-tail intermediates with increasing π-acidity of the ligand. The qualitative orbital treatment presented as an explanation is also applicable to reactions found for other metallacyclopentanes.