Ytterbium triflate

Base Information

• Chemical Name: Ytterbium triflate
• CAS No.: 54761-04-5
• Molecular Formula: C3F9O9S3Yb
• Molecular Weight: 620.251
• Hs Code.: 28469099
• European Community (EC) Number: 629-256-7,629-496-2
• UNII: 4N70OSW24G
• DSSTox Substance ID: DTXSID30369793
• Nikkaji Number: J1.021.255C
• Wikidata: Q27260229
• Mol file: 54761-04-5.mol

Synonyms:Yb(OTf)3;ytterbium(III) triflate;ytterbium(III) trifluoromethanesulfonate

Chemical Property of Ytterbium triflate

Chemical Property:

• Melting Point: 8 °C
• Boiling Point: 162 °C at 760 mmHg
• PSA: 155.25000
• LogP: 4.19310
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 0
• Exact Mass: 620.7949411
• Heavy Atom Count: 25
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

Ytterbium(III) trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].[Yb+3]
• Uses: Versatile rare earth metal catalyst in organic synthesis. Ytterbium(III) Trifluoromethanesulfonate functions as a catalyst in the organic synthesis of heterocycles. Also functions as a Lewis acid in variety of organic reactions.

Technology Process of Ytterbium triflate

There total 3 articles about Ytterbium triflate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ytterbium(III) oxide + trifluorormethanesulfonic acid (1493-13-6) → ytterbium(III) triflate (54761-04-5)

Guidance literature:

In water; Ln2O3 was mixed with excess trifluoromethanesulfonic acid at room temp. and heated at 80-90°C;

Reference yield:

trifluorormethanesulfonic acid (1493-13-6) + ytterbium → ytterbium(III) triflate (54761-04-5)

Guidance literature:

In water; reacted with aq. ligand; septd., dried for 24 h (200°C, 0.001 mbar);

DOI:10.1002/ejic.201000323

Reference yield:

Yb(OTf)3*9H2O → ytterbium(III) triflate (54761-04-5)

Guidance literature:

190°C;

upstream raw materials:

trifluorormethanesulfonic acid

Downstream raw materials:

3-[(4-nitrophenyl)(hydroxy)methyl]-1-[2-(methylsulfanyl)phenyl]prop-2-en-1-one

1-(1-{3-[5-acetyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-2-hydroxy-propyl}-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-one

1-[1-[2-hydroxy-3-(4-o-tolyl-piperazin-1-yl)-propyl]-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone

1-{3-(4-chloro-3-nitro-phenyl)-1-[2-hydroxy-3-(4-o-tolyl-piperazin-1-yl)-propyl]-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl}-ethanone

Refernces

Catalytic enantioselective total synthesis of (-)-platyphyllide and its structural revision

10.1021/jo1003746

The research focuses on the catalytic asymmetric total synthesis of platyphyllide, a norsesquiterpene lactone. The primary purpose of this study is to develop an efficient and enantioselective synthetic route to platyphyllide using a catalytic asymmetric Diels-Alder reaction, and to revise the absolute configuration of natural (-)-platyphyllide based on the synthesized compound. The key chemicals used in this research include Danishefsky diene, an electron-deficient alkene, Yb(OTf)3 as the central metal catalyst combined with axially chiral ligands (BINAMIDE or BINUREA), and various reagents for subsequent transformations such as Pd(OAc)2 for Ito-Saegusa oxidation and Grignard reagents. The study successfully synthesized platyphyllide through a series of reactions, including the Diels-Alder reaction to obtain a highly substituted cyclohexene derivative, followed by oxidation to a protected cyclohexane-1,3-dione, and further transformations to achieve the final product. The researchers discovered that the optical rotation of the synthesized platyphyllide was opposite to that of the natural compound, leading to the revision of the absolute configuration of natural (-)-platyphyllide to the (6S,7S)-enantiomer. This work not only provides a new synthetic method for platyphyllide but also clarifies its absolute stereochemistry through X-ray crystallographic analysis of a key intermediate.

Ytterbium triflate catalysed Meerwein-Ponndorf-Verley (MPV) reduction

10.1016/j.tetlet.2011.12.033

The research investigates the effectiveness of ytterbium triflate in catalyzing the Meerwein–Ponndorf–Verley (MPV) reduction of various substituted aromatic and aliphatic aldehydes and ketones using isopropanol as both the solvent and reducing agent. The study demonstrates that ytterbium triflate can efficiently promote this reduction process, yielding primary and secondary alcohols in yields ranging from 22% to 98%. The methodology involves dissolving the carbonyl compound and ytterbium triflate in isopropanol and stirring the mixture at reflux overnight. After solvent evaporation, catalyst recovery, and purification, the desired alcohols are obtained. Notably, the catalyst can be reused multiple times without significant loss of activity. The study concludes that ytterbium triflate offers a practical and environmentally friendly alternative for MPV reductions, with mild reaction conditions and satisfactory yields.

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