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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:
52093-29-5
Molecular Weight:
604.46
MDL number:
MFCD00192189
UNSPSC Code:
12161600
PubChem Substance ID:
24866617
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.[1]

pictograms

Exclamation mark
GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
0000225250
0000225250
0000198802
0000163287

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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
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
Kobayashi, S.; Nagayama, S.
Journal of the American Chemical Society, 119, 10049-10049 (1997)
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.
The Journal of Organic Chemistry, 59, 3590-3590 (1994)

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