Global InformationSodium chlorodifluoroacetate information
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3D model (JSmol)
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| ECHA InfoCard | 100.015.988 |
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CompTox Dashboard (EPA)
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Chemical formula
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C2ClF2NaO2 |
| Molar mass | 152.46 g·mol−1 |
| Appearance | white solid |
| Melting point | 196–198 °C (385–388 °F; 469–471 K) |
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Pictograms
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Warning |
Hazard statements
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H315, H319, H335 |
Precautionary statements
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P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Sodium chlorodifluoroacetate is the organofluorine compound with the formula CF2ClCO2Na.[2] 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:
- CF2ClCO2Na → NaCl + CF2 + CO2
This reaction is conducted in a hot solution also containing the substrate. Diglyme is a typical solvent.[2] The conversion of sodium chlorodifluoroacetate is proposed to start with decarboxylation, which generates the carbanion ClF2C−.
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[3] In this case, (C6H5)3P=CF2 is proposed as an intermediate.
- ^ "Sodium chlorodifluoroacetate". pubchem.ncbi.nlm.nih.gov.
- ^ 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.