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743232

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:
2926-29-6
Molecular Weight:
156.06
Beilstein:
3723394
MDL number:
MFCD03092989
UNSPSC Code:
12352101
PubChem Substance ID:
329765623
NACRES:
NA.22

Quality Level

100

Assay

≥95.0% (T)

form

powder

reaction suitability

reaction type: C-C Bond Formation

impurities

≤1.0% water (Karl Fischer)

mp

<325 °C

functional group

fluoro
sulfinic acid

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD3364
BCCC6879
BCCB0262
BCBX4470
BCBS9566V

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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
Innate CH trifluoromethylation of heterocycles.
Ji Y, et al.
Proceedings of the National Academy of Sciences of the USA, 108(35), 14411-14415 (2011)
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
Trifluoromethylation of aromatic compounds with sodium trifluoromethanesulfinate under oxidative conditions.
Langlois B R, et al.
Tetrahedron Letters, 32(51), 7525-7528 (1991)
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)
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