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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:
12352300
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)

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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)
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
Ytterbium triflate catalyzed synthesis of β-keto enol ethers.
Curini M, et al.
Tetrahedron Letters, 47(27), 4697-4700 (2006)
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
Snider, B.B. Liu, T.
The Journal of Organic Chemistry, 64, 1088-1088 (1999)
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Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

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