370-69-4

Usage

Uses

Used in Pharmaceutical Industry:
TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique reactivity allows for the formation of new molecules with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE is used as a reagent in the Arbuzov reaction. This reaction is a key step in the synthesis of N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide, which is an important compound in the development of new pharmaceuticals and other chemical products.
Used in Material Science:
TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE is also utilized in the development of new materials with specific properties, such as flame retardancy or improved thermal stability. Its unique structure and reactivity make it a valuable component in the creation of advanced materials for various applications.

Purification Methods

Fractionate it through a 10inch Helipak column [Krogh et al. J Org Chem 19 1124 1954]. Tris-[(3-trifluoromethylhydroxymethylene)-d-camphorato] europium (III) [Eu(tfc)3] [34830-11-0] M 893.6, m 195-299o (dec), ~220o, [ ] D +152o (c 2, CCl4, and varies markedly with concentration). Purify it by extraction with pentane, filter and the filtrate is evaporated and the residual bright yellow amorphous powder is dried at 100o/0.1mm for 36hours. A sample purified by fractional molecular distillation at 180-200o/0.004mm gave a liquid which solidified and softened at ~130o, and melted at ~180o and was analytically pure. IR (CCl4) 1630-1680cm-1 and NMR (CCl4) broad: -1.3 to 0.5, -0.08 (s), 0.41 max (s), 1.6-2.3 and 3.39 (s). [McCreary et al. J Am Chem Soc 96 1038 1974, Goering et al. J Am Chem Soc 93 5913 1971.]

InChI:InChI=1/C6H6F9O3P/c7-4(8,9)1-16-19(17-2-5(10,11)12)18-3-6(13,14)15/h1-3H2

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 121-44-8 triethylamine 
• 92466-70-1 bis(2,2,2-trifluoroethyl)phosphite 

Downstream Products

• 140476-67-1 bis<(diphenylmethylene)imino>tris(2,2,2-trifluoroethoxy)phosphorane 
• 140476-60-4 tetrakis(2,2,2-trifluoroethoxy)<α-(trifluoromethyl)benzylideneamino>phosphorane 
• 71181-76-5 pentakis(2,2,2-trifluoroethoxy)phosphorane 
• 76943-20-9 thiophenyltetrakis(2,2,2-trifluoroethoxy)phosphorane 
• 124841-97-0 1-Chloro-2,2,2-trifluoro-1-phenyl-ethyl-phosphorimidic acid tris-(2,2,2-trifluoro-ethyl) ester 
• 358-63-4 tris(2,2,2-trifluoroethyl) phosphate 
• 757-95-9 bis(2,2,2-trifluoroethyl)(methyl)phosphonate 
• 133338-72-4 2,2-Dibromovinyloxybis(2,2,2-trifluoroethoxy)phosphate 
• 178321-37-4 Phenylsulfanylmethyl-phosphonic acid bis-(2,2,2-trifluoro-ethyl) ester 
• 107905-52-2 ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate 
• 99687-58-8 Ni(P(CH₂CH₂P(C₆H₅)2)3)((P(OCH₂CF₃)3))⁽²⁺⁾*2BF₄^(1-) = {Ni(P(CH₂CH₂P(C₆H₅)2)3)(P(OCH₂CF₃)3)}(BF₄)2 
• 1067232-43-2 (S)-N⁽³⁾-[(bis-2'',2'',2''-trifluoroethoxyphosphoryl)methyl]-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 75-89-8 2,2,2-trifluoroethanol 
• 63036-16-8 tris(2,2,2-trifluoroethoxy)-N-(trimethylsilyl)phosphoranimine 

Relevant academic research and scientific papers

Fluorinated phosphorus compounds: Part 10. Bis(fluoroalkyl) S-alkyl phosphorothiolates and tris(fluoroalkyl) phosphorothionates

Treatment of bis(fluoroalkyl) phosphites (RFCH 2O)2P(O)H, where RF was CF3 or C2F5 with sulfur in pyridine at 80 °C gave salts of structure [(RFCH2O)2P(O)SH]NC5H 5 in 90 and 88% yield, respectively. The salts reacted with alkyl iodides in acetonitrile at 50 °C to furnish bis(fluoroalkyl) S-alkyl phosphorothiolates (RFCH2O)2P(O)SR, where R was Me, Et, n- and i-Pr (when RF = CF3) and Me (when R F = C2F5). Yields ranged from 21 to 57%. Bis(trifluoroethyl) S-methyl phosphorothiolate (CF3CH 2O)2P(O)SMe underwent fluorination by silver(I) fluoride in acetonitrile at room temperature to yield the phosphorofluoridate (CF 3CH2O)2P(O)F in 75% yield. Tris(fluoroalkyl) phosphorothionates (RFCH2O)3P = S, where R F was CF3, C2F5 and C 3F7, were prepared in 30-34% yield by heating the tris(fluoroalkyl) phosphites (RFCH2O)3P and sulfur to 200 °C in a sealed tube for 8 h. Crown Copyright

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.

Synthesis of Non-Symmetric Functionalized Polyfluoroalkyl Phosphites

Abstract: Two ways for the synthesis of new representatives of non-symmetric organicphosphites with polyfluoroalkyl substituents were developed based on organicdichlorophosphites. The reaction of polyfluoroalkyl dichlorophosphites withallyl alcohol, proce

Preparation method of tri(fluoroalkyl)phosphite

The invention discloses a preparation method of tris(fluoroalkyl)phosphite. The preparation method comprises the following steps: 1, dropwise adding phosphorus trichloride into fluorinated fatty alcohol or fluorinated phenyl alkyl alcohol for reaction; and 2, after the reaction is finished, adding an organic solvent and deionized water, carrying out low-temperature water washing, carrying out standing and liquid separation, separating out an organic phase, rectifying the organic phase, and collecting a finished product of the tri(fluoroalkyl)phosphite. The method has the advantages that underthe condition that the yield is guaranteed, impurities in the preparation process of the tri(fluoroalkyl)phosphite can be effectively removed, and therefore a high-purity target product can be obtained through rectification.

Efficient methods for the synthesis of α-aminophosphonate fluoroalkyl esters

Two novel synthetic methods for the preparation of bis(trifluoroethyl) esters of α-aminophosphonic acids are presented. Preliminary results on the application of the compounds synthesized as inhibitors of serine proteases are also reported. Structures originating from α-aminoalkylphosphonate diaryl esters represent a novel class of serine protease inactivators.

Design, synthesis and in vitro evaluation of mono (2, 2, 2-trifluoroethyl) esters, mono l-amino acid ester prodrugs of acyclic nucleoside phosphonates as anti-HBV agents

A series of novel mono (2, 2, 2-trifluoroethyl) esters, mono l-amino acid ester prodrugs of acyclic nucleoside phosphonates was synthesized and their in vitro anti-HBVactivity was evaluated in HepG 2 2.2.15 cells. Compound 1d exhibited more potent anti-HB

The kinetics and mechanism of the reaction of tricoordinate phosphorus compounds with sulfenate esters

The kinetics and mechanism of the reaction of tricoordinate phosphorus compounds, ArnP(OCH2CF3)3-n with arylsulfenate esters, ArSOCH2CF3, are reported. Product analysis, kinetic order, activation parameters, Hammett data and solvent effects are the criteria used to elucidate the two step mechanism involving arylthiophosphoranes as intermediates.

THE THERMOLYTIC DECOMPOSITION OF ACYCLIC PHOSPHORANES

The thermolytic decomposition of acyclic phosphoranes, ArnP(OCH2CF3)5-n in aprotic media has been shown by kinetic studies to proceed via rate-limiting ionization of the phosphoranes.Activation parameters, deuterium isotope effects, solvent effects and ρ-values (for n = 3 and n = 1) support this concept which is consistent with the observed rate-sequence of n = 3> n = 2 > n = 1 > n = 0.Key words: Phosphoranes, thermolysis, kinetics, mechanism.

Synthesis and separation of diastereoisomers of O-(2,2,2-trifluoroethyl)-3',5'-dinucleoside phosphates

The synthesis, diastereomeric separation, and characterization are described for a series of novel O-(2,2,2-trifluoroethyl)-3',5'-dinucleoside phosphates, required for incorporation into antisense probes in the magnetic resonance imaging investigation of

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.