Sodium chlorodifluoroacetate

Sodium chlorodifluoroacetate
Identifiers
CAS Number	1895-39-2;
3D model (JSmol)	Interactive image;
ChemSpider	67266;
ECHA InfoCard	100.015.988
EC Number	217-586-0;
PubChem CID	2734985;
UNII	ZAY4J838P2;
CompTox Dashboard (EPA)	DTXSID1062049 ;
	InChI InChI=1S/C2HClF2O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1 Key: MRTAVLDNYYEJHK-UHFFFAOYSA-M;
	SMILES 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:
Pictograms
Signal word	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

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

^ "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.

[1] "Sodium chlorodifluoroacetate". pubchem.ncbi.nlm.nih.gov.

[eEROS-2] 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.

[1]