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905771 Sigma-Aldrich

Dimethylsulfoxonium-3-(methyl)benzoylmethylide

≥95%

Synonym: 2-(Dimethyl(oxo)-sulfaneylidene)-1-(m-tolyl)ethan-1-one

  • CAS Number 2118974-84-6

  • Empirical Formula (Hill Notation) C11H14O2S

  • Molecular Weight 210.29

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Properties

Related Categories Chemical Synthesis, Sulfoxonium Ylides, Synthetic Reagents More...
assay   ≥95%
form   solid
mp   120-121 °C
storage temp.   −20°C
SMILES string   O=C(C1=CC=CC(C)=C1)C=S(C)(C)=O

Description

General description

Sulfoxonium ylides are highly stable carbene precursors, serving as a safer alternative to diazo compounds as they that do not generate gases as byproducts. Sulfoxonium ylides have been shown to be effective in a wide array of transition metal catalyzed C-H functionalization and coupling reactions.

Other Notes

For additional technical information see Ketosulfoxonium Ylides: Safe, Versatile Carbene Equivalents

Rhodium(III)-Catalyzed Imidoyl C-H Activation for Annulations to Azolopyrimidines

Safety & Documentation

Safety Information

WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Ellman Group – Professor and Product Portal

From our library of Articles, Sigma-Aldrich presents Ellman Group – Professor and Product Portal
Keywords: Arylations, Asymmetric synthesis, C-C bond formation, Catalysis, Drug discovery, Ligands, Pharmaceutical

Ketosulfoxonium Ylides

Since Corey and Chaykovsky first investigated ketosulfoxonium ylides in the 1960s,1  these reagents have become increasingly popular as stable and safe α-diazocarbonyl equivalents, including for larg...
Keywords: Annulations, Catalysis, Drug discovery

Peer-Reviewed Papers
15

References

Related Products

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905860 Dimethylsulfoxonium-4-(chloro)benzoylmethylide, ≥95%
905763 Dimethylsulfoxonium-4-(trifluoromethyl)benzoylmethylide, ≥95%
905798 Dimethylsulfoxonium-(isobutanoyl)methylide, ≥95%
905828 Dimethylsulfoxonium-3-(chloro)benzoylmethylide, ≥95%
905844 Dimethylsulfoxonium-4-(fluoro)benzoylmethylide, ≥95%
905704 Dimethylsulfoxonium-(N-Boc(4-piperidinecarbonoyl)methylide, ≥95%
905690 Dimethylsulfoxonium-2-(chloro)benzoylmethylide, ≥95%
905682 Dimethylsulfoxonium-3-(pyridoyl)methylide, ≥95%
905674 Dimethylsulfoxonium-2-(thiophenoyl)methylide, ≥95%

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