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Merck
CN

905682

Dimethylsulfoxonium-3-(pyridoyl)methylide

≥95%

Synonym(s):

2-(Dimethyl(oxo)-sulfaneylidene)-1-(pyridin-3-yl)ethan-1-one

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About This Item

Empirical Formula (Hill Notation):
C9H11NO2S
CAS Number:
2218518-58-0
Molecular Weight:
197.25
UNSPSC Code:
12352005

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SMILES string

O=C(C1=CC=CN=C1)C=S(C)(C)=O

assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

133-135 °C

functional group

ketone, sulfoxide

storage temp.

−20°C

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 C−H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused[5,6]-bicyclic heterocycles

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Gia L Hoang et al.
Tetrahedron, 74(26), 3318-3324 (2018-07-11)
The synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles via rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides is disclosed. Reactions proceeded in good to high yields for a range of aryl, heteroaryl and alkyl sulfoxonium ylides. In addition, 2-alkenyl imidazoles

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Ketosulfoxonium Ylides

Ketosulfoxonium ylides serve as versatile carbene equivalents for large-scale reactions, releasing dimethyl sulfoxide biproducts.

Ellman Group – Professor Product Portal

Ellman group developed electron-rich phosphine ligands for C-H functionalization and tert-Butanesulfinamide for asymmetric amine synthesis.

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