370-69-4

Basic information

• Product Name: TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE
• Synonyms: Phosphite, tris(2,2,2-trifluoroethyl);TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE;TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE, 99 %;Tris(2,2,2-trifluoroethyl) phosphite 99%;TTFP
• CAS NO: 370-69-4
• Molecular Formula: C₆H₆F₉O₃P
• Molecular Weight: 328.07
• Product Categories: Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds
• Mol File: 370-69-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 130-131 °C743 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.487 g/mL at 25 °C(lit.)
• Vapor Pressure: 12.7mmHg at 25°C
• Refractive Index: n20/D 1.324(lit.)
• BRN: 1714041
• CAS DataBase Reference: TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE(370-69-4)
• EPA Substance Registry System: TRIS(2,2,2-TRIFLUOROETHYL) PHOSPHITE(370-69-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 370-69-4(Hazardous Substances Data)

Usage

Uses

Tris(2,2,2-trifluoroethyl) phosphite was used in the synthesis of N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide via the Arbuzov reaction with 2-bromo-N-methoxy-N-methylacetamide.

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

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 
• 358-63-4 tris(2,2,2-trifluoroethyl) phosphate 
• 133338-72-4 2,2-Dibromovinyloxybis(2,2,2-trifluoroethoxy)phosphate 
• 1228992-66-2 C₂₉H₂₇F₉NO₅P 
• 1228992-37-7 C₂₆H₂₂N₂O 
• 28212-50-2 C₂₅H₂₁F₉NO₃P 
• 28212-50-2 C₁₃H₁₃F₉NO₃P 
• 624-31-7 4-tolyl iodide 
• 108-88-3 toluene 
• 253185-03-4 tert-butylbenzene 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 1428647-08-8 bis(2,2,2-trifluoroethyl) tert-butylphenylphosphonate 

Relevant articles and documents

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

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.