757-95-9

Basic information

• Product Name: BIS(2 2 2-TRIFLUOROETHYL)METHYLPHOSPHON&
• Synonyms: BIS(2 2 2-TRIFLUOROETHYL)METHYLPHOSPHON&;BIS(TRIFLUOROETHYL)METHYLPHOSPHONATE, 9&;bis(2,2,2-trifluoroethyl) methylphosphonate;Bis(2,2,2-trifluoroethyl) methylphosphonate 98%;1,1,1-trifluoro-2-[methyl(2,2,2-trifluoroethoxy)phosphoryl]oxyethane
• CAS NO: 757-95-9
• Molecular Formula: C₅H₇F₆O₃P
• Molecular Weight: 260.069
• Product Categories: C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 757-95-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 24-28 °C(lit.)
• Boiling Point: 183-184 °C(lit.)
• Flash Point: 176 °F
• Appearance: /
• Density: 1.439g/cm³
• Vapor Pressure: 2.85mmHg at 25°C
• Refractive Index: n20/D 1.339(lit.)
• CAS DataBase Reference: BIS(2 2 2-TRIFLUOROETHYL)METHYLPHOSPHON&(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(2 2 2-TRIFLUOROETHYL)METHYLPHOSPHON&(757-95-9)
• EPA Substance Registry System: BIS(2 2 2-TRIFLUOROETHYL)METHYLPHOSPHON&(757-95-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 757-95-9(Hazardous Substances Data)

Usage

Description

BIS(2,2,2-TRIFLUOROETHYL)METHYLPHOSPHON& is a chemical compound with a unique structure that features two trifluoroethyl groups attached to a central phosphonate group. BIS(2 2 2-TRIFLUOROETHYL)METHYLPHOSPHON& exhibits versatile properties and has been identified for its potential applications in various fields.

Uses

Used in Chemical Synthesis:
BIS(2,2,2-TRIFLUOROETHYL)METHYLPHOSPHON& is used as a reactant for the synthesis of fluorescently labeled discodermolide, which is crucial for studying its binding to tubulin, a protein that plays a significant role in cell division and intracellular transport.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BIS(2,2,2-TRIFLUOROETHYL)METHYLPHOSPHON& is used as a reactant for the synthesis of the anticancer microtubule-stabilizing macrolide, (-)-dictyostatin. BIS(2 2 2-TRIFLUOROETHYL)METHYLPHOSPHON& has potential applications in the development of new cancer treatments.
Used in Organic Catalysis:
BIS(2,2,2-TRIFLUOROETHYL)METHYLPHOSPHON& is used as a homogenous organic catalytic system and as a catalyst for the phosphorylation of polyfluoroalkanols. This application highlights its potential in facilitating chemical reactions and improving the efficiency of synthesis processes.
Used in Material Science:
In the field of material science, BIS(2,2,2-TRIFLUOROETHYL)METHYLPHOSPHON& is used as a flame-retardant additive for lithium-ion electrolytes. This application is crucial for enhancing the safety and performance of lithium-ion batteries, which are widely used in various electronic devices and electric vehicles.
Used in Chemical Reactions:
BIS(2,2,2-TRIFLUOROETHYL)METHYLPHOSPHON& is employed in cross metathesis and phosphonate-based intramolecular olefination reactions. These reactions are essential for the synthesis of complex organic molecules and the development of new chemical compounds with potential applications in various industries.

InChI:InChI=1/C5H7F6O3P/c1-15(12,13-2-4(6,7)8)14-3-5(9,10)11/h2-3H2,1H3

Upstream product

• 676-97-1 methylphosphonic acid dichloroanhydride 
• 75-89-8 2,2,2-trifluoroethanol 
• 370-69-4 tris(2,2,2-trifluoroethyl)phosphite 
• 74-88-4 methyl iodide 
• 13113-88-7 Dichlormethyl-phosphonsaeure 
• 756-79-6 dimethyl methane phosphonate 
• 92466-70-1 bis(2,2,2-trifluoroethyl)phosphite 
• 134751-06-7 tris(2,2,2-trifluoroethoxy)methylphosphonium triflate 

Downstream Products

• 1097160-42-3 C₂₀H₂₅F₆O₆P 
• 312695-84-4 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 7-{3-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-2-methyl-propyl}-1-[1-(4-methoxy-benzyloxy)-3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-5-methoxymethoxy-octa-3,7-dienyl ester 
• 312695-95-7 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 1-[1-(4-methoxy-benzyloxy)-3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-5-methoxymethoxy-7-{2-methyl-3-[6-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-2-yl]-propyl}-octa-3,7-dienyl ester 
• 135690-95-8 Benzyl acetate 
• 124755-24-4 ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate 
• 1383610-28-3 tert-butyl 3-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-oxopropylcarbamate 
• 1345025-43-5 bis(2,2,2-trifluoroethyl) 2-[2,4-bis(methoxymethoxy)phenyl]-2-oxoethylphosphonate 
• 939383-45-6 C₂₀H₂₄F₆IO₆P 
• 1097160-33-2 C₁₉H₂₂F₆IO₆P 
• 334936-14-0 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 2,4-dimethoxy-benzyl ester 

Relevant articles and documents

Correction of Q Factor Effects for Simultaneous Collection of Elemental Analysis and Relaxation Times by Nuclear Magnetic Resonance

A new method for measurement of elemental analysis by nuclear magnetic resonance (NMR) of unknown samples is discussed here as a quick and robust means to measure elemental ratios without the use of internal or external calibration standards. The determination of elemental ratios was done by normalizing the signal intensities by the frequency dependent quality factor (Q) and the gyromagnetic ratios (?) for each measured nucleus. The correction for the frequency dependence was found by characterizing the output signal of the probe as a function of the quality factor (Q) and the frequency, and the correction for γwas discussed in a previous study. A Carr-Purcell-Meiboom-Gill (CPMG) pulse sequence was used for evaluation of the relative signal intensities, which allows for derivation of elemental ratios, and was correspondingly used to simultaneously measure the T2? of samples for an added parameter for more accurate identification of unknown samples.

A Green Process for the Preparation of Bis(2,2,2-trifluoroethyl) Methylphosphonate

Bis(trifluoroethyl) methylphosphonate is the starting material for the synthesis of Jin's reagent. Jin's reagent is widely used for the preparation of (Z)-α,β-unsaturated ketones and is also a valuable potent flame-retardant additive. Preparation of bis(trifluoroethyl) methylphosphonate was investigated by direct transesterification of dimethyl methylphosphonate with 2,2,2-trifluoroethanol (further trifluoroethanol, TFE), being a well-known weak nucleophile, using microwave and flow reactors. Direct transesterification was successful in a continuous flow reactor at 450 °C and 200 bar using a highly diluted reaction mixture. The product, bis(trifluoroethyl) methylphosphonate, was purified by column chromatography, and excess trifluoroethanol was recovered by distillation.

LAULIMALIDE ANALOGS AND USES THEREOF

The present invention provides compounds having formula 1: (I) and pharmaceutically acceptable derivatives thereof, wherein R1-R10, q, t, X0, X1, A, B, D, E, G, J, K, L, M and Z are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders associated with cellular hyperproliferation.