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405329

Sigma-Aldrich

Ytterbium(III) trifluoromethanesulfonate hydrate

Yb 25-28 % (approx.)

Synonym(s):

Yb(OTf)3, Trifluoromethanesulfonic acid ytterbium salt, Ytterbium(III) triflate

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About This Item

Linear Formula:
(CF3SO3)3Yb · xH2O
CAS Number:
252976-51-5
Molecular Weight:
620.25 (anhydrous basis)
MDL number:
MFCD03703499
UNSPSC Code:
12161600
PubChem Substance ID:
24865309
NACRES:
NA.22

composition

Degree of hydration, 1-2
Yb, 25-28% (approx.)

reaction suitability

core: ytterbium
reagent type: catalyst

SMILES string

[H]O[H].FC(F)(F)S(=O)(=O)O[Yb](OS(=O)(=O)C(F)(F)F)OS(=O)(=O)C(F)(F)F

InChI

1S/3CHF3O3S.H2O.Yb/c3*2-1(3,4)8(5,6)7;;/h3*(H,5,6,7);1H2;/q;;;;+3/p-3

InChI key

BUJKNFNMGRYZBV-UHFFFAOYSA-K

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General description

Layer-by-layer assembly of 4-aminothiophenol and ytterbium(III)trifluoromethanesulfonate hydrate film has been investigated by atomic force microscopy (AFM). Bis(oxazolinyl)-pyridine-scandium(III) triflate complexes have been reported to catalyze the enantioselective Friedel-Crafts addition of various indoles.

Application

Ytterbium(III) trifluoromethanesulfonate hydrate (Yb(OTf)3) was employed as Lewis acid catalyst for the following studies:
  • Synthesis of the dihydropyrimidine (DHPM) derivative monastrol, by Biginelli cyclocondensation.
  • Cross-aldol reaction between ketone and aldehyde.
  • Synthesis of β-keto enol ethers.
  • Synthesis of deoxypenostatin A in a novel, stereoselective intramolecular Diels-Alder reaction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ytterbium triflate catalyzed synthesis of β-keto enol ethers.
Curini M, et al.
Tetrahedron Letters, 47(27), 4697-4700 (2006)
David A Evans et al.
Journal of the American Chemical Society, 129(32), 10029-10041 (2007-07-31)
The enantioselective Friedel-Crafts addition of a variety of indoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes (Sc(III)-pybox) was accomplished utilizing a series of beta-substituted alpha,beta-unsaturated phosphonates and alpha,beta-unsaturated 2-acyl imidazoles. The acyl phosphonate products were efficiently transformed into esters and amides, whereas
Snider, B.B. Liu, T.
The Journal of Organic Chemistry, 64, 1088-1088 (1999)
Doris Dallinger et al.
Nature protocols, 2(2), 317-321 (2007-04-05)
We present here a protocol for the synthesis of the dihydropyrimidine (DHPM) derivative monastrol, which is known to be a specific mitotic kinesin Eg5 inhibitor. By applying controlled microwave heating under sealed-vessel conditions, the synthesis via the one-pot three-component Biginelli
Ytterbium Trifluoromethanesulfonate Mediated Cross-Aldol Reaction between Ketones and Aldehydes.
Fukuzawa S-I, et al.
Bulletin of the Chemical Society of Japan, 67(8), 2227-2232 (1994)
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Articles

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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