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Documentos

905690

Sigma-Aldrich

Dimethylsulfoxonium-2-(chloro)benzoylmethylide

≥95%

Sinónimos:

1-(2-Chlorophenyl)-2-(dimethyl(oxo)-sulfaneylidene)ethan-1-one

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About This Item

Fórmula empírica (notación de Hill):
C10H11ClO2S
Número de CAS:
2118974-86-8
Peso molecular:
230.71
UNSPSC Code:
12352101

assay

≥95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

136-137 °C

storage temp.

−20°C

SMILES string

O=C(C1=CC=CC=C1Cl)C=S(C)(C)=O

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

Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Prochiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones

Related product

Referencia del producto
Descripción
Precios

905860

Dimethylsulfoxonium-4-(chloro)benzoylmethylide, ≥95%

905763

Dimethylsulfoxonium-4-(trifluoromethyl)benzoylmethylide, ≥95%

905771

Dimethylsulfoxonium-3-(methyl)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%

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Alexánder Garay Talero et al.
Organic letters, 20(22), 7206-7211 (2018-10-27)
A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible β-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a
Youwei Xu et al.
Organic letters, 19(16), 4307-4310 (2017-08-08)
Direct and efficient synthesis of 1-naphthols has been realized via Rh(III)-catalyzed C-H activation of sulfoxonium ylides and subsequent annulation with alkynes, where the sulfoxonium ylide functioned as a new traceless bifunctional directing group. This reaction occurred under redox-neutral conditions with
Panjie Hu et al.
Organic letters, 20(8), 2160-2163 (2018-04-03)
Rh(III)-catalyzed cascade C-H activation of benzoylacetonitriles and annulation with sulfoxonium ylides was realized, leading to selective synthesis of naphthols, 2,3-dihydronaphtho[1,8- bc]pyrans, and naphtho[1,8- bc]pyrans. This step-economic reaction proceeded efficiently under mild and redox-neutral conditions via multiple C-H activations.

Contenido relacionado

Ketosulfoxonium Ylides

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

Ellman Group – Professor Product Portal

The Ellman group has participated in the development of a variety of C-H functionalization methods. An electron rich phosphine ligand has proven to be very useful for a variety of Rh(I)-catalyzed C-C bond forming reactions applicable to heterocycle synthesis as exemplified in the recent Science paper “Proton Donor Acidity Controls Selectivity in Nonaromatic Nitrogen Heterocycle Synthesis.” Another useful ligand developed for the highly functional group compatible direct arylation of nitrogen heterocycles is described in a 2008 J. Am. Chem. Soc. paper “Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope through Mechanistic Insight.” The Ellman group also developed the chiral amine reagent tert-Butanesulfinamide, which is extensively used in academics and industry for the asymmetric synthesis of amines. A comprehensive survey of tert-Butanesulfinamide methods and applications up through 2009 is provided in the 2010 Chemical Reviews article, “Synthesis and Applications of tert-Butanesulfinamide.”

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