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425176

Sigma-Aldrich

Gadolinium(III) trifluoromethanesulfonate

98%

Synonym(s):

Tris(trifluoromethanesulfonato)gadolinium, Gadolinium(III) triflate

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About This Item

Linear Formula:
(CF3SO3)3Gd
CAS Number:
Molecular Weight:
604.46
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

assay

98%

reaction suitability

core: gadolinium
reagent type: catalyst

SMILES string

[Gd+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

1S/3CHF3O3S.Gd/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

InChI key

DYOBTPTUHDTANY-UHFFFAOYSA-K

Application

A water-tolerant Lewis acid used in the Aldol reaction of silyl enol ethers with aldehydes.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Yamanaka et al.
Organic letters, 2(2), 159-161 (2000-05-18)
[reaction: see text] Ytterbium trifluoromethanesulfonate [Yb(OTf)3] catalyzed the imino ene reaction of N-tosyl aldimine with alpha-methylstyrene to give a homoallylamine in moderate yield. Furthermore, addition of a catalytic amount of chlorotrimethylsilane (TMSCI) dramatically enhanced the imino ene reaction.
Tomoaki Hamada et al.
Journal of the American Chemical Society, 125(10), 2989-2996 (2003-03-06)
Catalytic asymmetric aldol reactions in aqueous media have been developed using Pr(OTf)(3) and chiral bis-pyridino-18-crown-6 1. In the asymmetric aldol reaction using rare earth metal triflates (RE(OTf)(3)) and 1, slight changes in the ionic diameters of the metal cations greatly
David A Evans et al.
Journal of the American Chemical Society, 125(34), 10162-10163 (2003-08-21)
A highly enantioselective, quinone Diels-Alder reaction catalyzed by chiral samarium and gadolinium pyridyl-bis(oxazoline) (pybox) complexes has been developed. The reaction scope has been extended to include three quinones and five dienes, all of which exclusively provide the expected endo product
Kobayashi, S.; Nagayama, S.
Journal of the American Chemical Society, 119, 10049-10049 (1997)
The Journal of Organic Chemistry, 59, 3590-3590 (1994)

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