Sodium chlorodifluoroacetate

Sodium chlorodifluoroacetate
Identifiers
CAS Number
  • 1895-39-2
3D model (JSmol)
  • Interactive image
ChemSpider
  • 67266
ECHA InfoCard 100.015.988 Edit this at Wikidata
EC Number
  • 217-586-0
PubChem CID
  • 2734985
UNII
  • ZAY4J838P2
CompTox Dashboard (EPA)
  • DTXSID1062049 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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]
Pictograms
 GHS07: Exclamation mark
Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 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
Chemical compound

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

  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.