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Sodium chlorodifluoroacetate

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Sodium chlorodifluoroacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.988 Edit this at Wikidata
EC Number
  • 217-586-0
UNII
  • InChI=1S/C2HClF2O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1
    Key: MRTAVLDNYYEJHK-UHFFFAOYSA-M
  • C(=O)(C(F)(F)Cl)[O-].[Na+]
Properties
C2ClF2NaO2
Molar mass 152.46 g·mol−1
Appearance white solid
Melting point 196–198 °C (385–388 °F; 469–471 K)
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
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).

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.

References

[edit]
  1. ^ "Sodium chlorodifluoroacetate". pubchem.ncbi.nlm.nih.gov.
  2. ^ a b Taschner, Michael J. (2001). "Sodium Chlorodifluoroacetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rs058. ISBN 0-471-93623-5.
  3. ^ Fuqua, Samuel A.; Duncan, Warren G.; Silverstein, Robert M. (1967). "β,β-Difluorostyene". Organic Syntheses. 47: 49. doi:10.15227/orgsyn.047.0049.