Sodium chlorodifluoroacetate
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| Identifiers | |
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| ECHA InfoCard | 100.015.988 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C2ClF2NaO2 | |
| Molar mass | 152.46 g·mol−1 |
| Appearance | white solid |
| Melting point | 196–198 °C (385–388 °F; 469–471 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sodium chlorodifluoroacetate is the organofluorine compound with the formula CF2ClCCO2Na.[1] It is a salt formed by neutralization of chlorodifluoroacetic acid with sodium hydroxide. The compound, a white solid, is of interest as a source of difluorocarbene:
- CF2ClCCO2Na → NaCl + CF2 + CO2
The carbanion ClF2C− is a proposed intermediate, being formed by an initial decarboxylation. This reaction is often conducted in hot diglyme as a solvent.[1]
One set of applications is difluorocyclopropanation. Thermal decomposition of sodium chlorodifluoroacetate in the presence of triphenylphosphine and an aldehyde allows for a Wittig-like reactions[2] In this case, (C6H5)3P=CF2 is proposed as an intermediate.
References
- ^ a b Taschner, Michael J. (2001). "Sodium Chlorodifluoroacetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rs058. ISBN 0-471-93623-5.
- ^ Fuqua, Samuel A.; Duncan, Warren G.; Silverstein, Robert M. (1967). "β,β-Difluorostyene". Organic Syntheses. 47: 49. doi:10.15227/orgsyn.047.0049.