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Merck
CN

405329

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)
NACRES:
NA.22
PubChem Substance ID:
24865309
UNSPSC Code:
12161600
MDL number:
MFCD03703499

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InChI

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

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 key

BUJKNFNMGRYZBV-UHFFFAOYSA-K

composition

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

reaction suitability

core: ytterbium, reagent type: catalyst

Related Categories

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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
0000313319
0000313319
0000179411
0000179403
0000179411

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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
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)
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
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Articles

Friedel–Crafts Acylation

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

傅-克酰基化反应

傅-克酰基化反应是一种芳烃与酰氯或酸酐使用强路易斯酸催化剂的反应。该反应通过亲电芳族取代进行，形成单酰化产物。

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