methyl P P-bis(2 2 2-trifluoroethyl) phosphonoacetate（CAS# 88738-78-7)
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29319090 |
Application
Methyl P,P-bis(2,2,2-trifluoroethyl)phosphonoacetate (CAS 88738-78-7, C₇H₉F₆O₅P, MW 318.11), also known as the Still-Gennari reagent, is a specialized phosphonoacetate ester used as a powerful Horner-Wadsworth-Emmons (HWE) reagent for the highly Z-selective synthesis of α,β-unsaturated esters from aldehydes and ketones. The presence of the electron-withdrawing bis(trifluoroethyl) groups significantly enhances the reactivity and Z-selectivity of the reagent compared to standard HWE reagents (e.g., triethyl or dimethyl phosphonoacetates), making it an indispensable tool in modern organic synthesis.
This reagent is widely used in the total synthesis of complex natural products and bioactive molecules. It has been employed in key synthetic steps for the preparation of trans-hydrindanes and (R)-(+)-umbelactone. Beyond these specific targets, it is a critical building block in medicinal chemistry for constructing Z-alkene-containing pharmaceuticals, peptidomimetics, and other biologically active compounds where stereochemical control is essential. Its utility extends to the synthesis of novel phosphonoacetates bearing stereogenic phosphorus atoms for asymmetric HWE reactions.
The compound is typically supplied as a liquid with a purity of ≥95% (GC). It has a density of 1.504 g/mL and a flash point of >110°C. Its solubility in water is approximately 11 g/L at 25°C. As a high-value research chemical, methyl bis(trifluoroethyl)phosphonoacetate is exclusively intended for life science research and is not for diagnostic or therapeutic use.
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