Sodium trifluoromethanesulfinate

Sodium trifluoromethanesulfinate (CF₃SO₂Na) is the sodium salt of trifluoromethanesulfinic acid. Together with t-butyl hydroperoxide, an oxidant, this compound was found to be a suitable reagent for introducing trifluoromethyl groups onto electron-rich aromatic compounds by Langlois; this reagent is also known as the Langlois reagent. This reaction operates via a free radical mechanism.^[1]

Sodium trifluoromethanesulfinate

Structure of sodium trifluoromethylsulfinate
Names
Preferred IUPAC name Sodium trifluoromethanesulfinate
Identifiers
CAS Number	2926-29-6
3D model (JSmol)	Interactive image
ChemSpider	2059266
ECHA InfoCard	100.203.570
PubChem CID	23690734
CompTox Dashboard (EPA)	DTXSID50635644
InChI InChI=1S/CHF3O2S.Na/c2-1(3,4)7(5)6;/h(H,5,6);/q;+1/p-1 Key: KAVUKAXLXGRUCD-UHFFFAOYSA-M InChI=1/CHF3O2S.Na/c2-1(3,4)7(5)6;/h(H,5,6);/q;+1/p-1 Key: KAVUKAXLXGRUCD-REWHXWOFAL
SMILES [Na+].FC(F)(F)S([O-])=O
Properties
Chemical formula	CF3NaO2S
Molar mass	156.05 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

This reagent is also able to trifluoromethylate electron-deficient aromatic compounds under biphasic conditions.^[2] Zinc difluoromethanesulfinate, a related polymeric coordination complex, is able to introduce difluoromethyl groups (CHF₂-) onto aromatic compounds under similar biphasic conditions as well.^[3]

With the use of DMSO as an oxidant, it provides an environmentally friendly way for the synthesis of β-trifluoromethyl alcohols from alkenes.^[4]