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Sigma-Aldrich

Sodium triflinate

≥95.0% (T)

Synonym(s):

Langlois reagent, Sodium trifluoromethanesulfinate, Sodium trifluoromethylsulfinate, Trifluoromethanesulfinic acid sodium salt

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About This Item

Empirical Formula (Hill Notation):
CF3NaO2S
CAS Number:
Molecular Weight:
156.06
Beilstein/REAXYS Number:
3723394
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95.0% (T)

form

powder

reaction suitability

reaction type: C-C Bond Formation

impurities

≤1.0% water (Karl Fischer)

mp

<325 °C

SMILES string

[Na+].[O-]S(=O)C(F)(F)F

InChI

1S/CHF3O2S.Na/c2-1(3,4)7(5)6;/h(H,5,6);/q;+1/p-1

InChI key

KAVUKAXLXGRUCD-UHFFFAOYSA-M

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Application

Sodium triflinate (Langlois reagent) is a trifluoromethylating reagent used to incorporate trifluoromethyl groups onto aromatic and heteroaromatic moieties.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Joachim Demaerel et al.
Ultrasonics sonochemistry, 41, 134-142 (2017-11-16)
Direct sonication by means of ultrasound horns constitutes a widely used technique in chemical process technology. However, the direct contact between the metal probe and the reaction mixture does not always leave the chemical system unaffected. In this report, we
Indrajit Ghosh et al.
Science (New York, N.Y.), 365(6451), 360-366 (2019-07-28)
Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here
Yulia A Konik et al.
Organic & biomolecular chemistry, 15(21), 4635-4643 (2017-05-18)
Tertiary cyclopropanols easily available from carboxylic esters have been used in the synthesis of distally fluorinated ketones. Cyclopropane ring cleavage reactions in methanol with aqueous tert-butyl hydroperoxide in the presence of a copper(ii) acetate catalyst and sodium triflinate (Langlois reagent)
Trifluoromethylation of aromatic compounds with sodium trifluoromethanesulfinate under oxidative conditions.
Langlois B R, et al.
Tetrahedron Letters, 32(51), 7525-7528 (1991)
Innate CH trifluoromethylation of heterocycles.
Ji Y, et al.
Proceedings of the National Academy of Sciences of the USA, 108(35), 14411-14415 (2011)

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