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Merck

767840

Sigma-Aldrich

Zinc difluoromethanesulfinate

95%

Sinónimos:

Bis(((difluoromethyl)sulfinyl)oxy)zinc, 1,1-difluoro-methanesulfinic acid zinc salt (2:1), Baran difluoromethylation reagent, DFMS

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About This Item

Fórmula empírica (notación de Hill):
C2H2F4O4S2Zn
Número de CAS:
Peso molecular:
295.55
Número MDL:
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Ensayo

95%

Formulario

solid

idoneidad de la reacción

reaction type: C-C Bond Formation
reaction type: Fluorinations
reagent type: catalyst
reaction type: C-H Activation

reagent type: diversification reagent

grupo funcional

fluoro
sulfinic acid

temp. de almacenamiento

2-8°C

cadena SMILES

FC(F)S(=O)O[Zn]OS(=O)C(F)F

InChI

1S/2CH2F2O2S.Zn/c2*2-1(3)6(4)5;/h2*1H,(H,4,5);/q;;+2/p-2

Clave InChI

UGEYAPVLXKEKMP-UHFFFAOYSA-L

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Descripción general

Material is complexed with up to 1 equivalent of ZnCl2
Zinc difluoromethanesulfinate is a reagent widely used to incorporate difluoromethyl functionality onto biologically significant structural motifs. It is used to difluoromethylate compounds such as heteroarenes, thiols, enones, and α, β‐unsaturated carboxylic acids.

Aplicación

Zinc difluoromethanesulfinate (DFMS) is part of a zinc sulfinate toolbox developed by Phil Baran for the simple and rapid diversification of heterocycles.†

Practical and Innate Carbon-Hydrogen Functionalization of Heterocycles

DFMS is a new reagent for direct difluoromethylation of organic substrates via a radical process. This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated p−systems and thiols.†

A New Reagent for Direct Difluoromethylation

Learn More at the Professor and Product Portal of Professor Phil S. Baran.

Ligadura / enlace

Frequently Asked Questions are available for this Product.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Jessy Aziz et al.
Organic & biomolecular chemistry, 12(48), 9743-9759 (2014-10-31)
Sulfinic acids and their salts have recently emerged as versatile coupling partners to efficiently access a wide variety of hetero- and carbocyclic compounds, under relatively mild conditions. Their growing importance is attributable to their dual capacity for acting as nucleophilic
Zinc difluoromethanesulfinate
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2014)
Yuta Fujiwara et al.
Journal of the American Chemical Society, 134(3), 1494-1497 (2012-01-11)
Molecular scaffolds containing alkylfluorine substituents are desired in many areas of chemical research from materials to pharmaceuticals. Herein, we report the invention of a new reagent (Zn(SO(2)CF(2)H)(2), DFMS) for the innate difluoromethylation of organic substrates via a radical process. This
Yuta Fujiwara et al.
Nature, 492(7427), 95-99 (2012-12-04)
Nitrogen-rich heterocyclic compounds have had a profound effect on human health because these chemical motifs are found in a large number of drugs used to combat a broad range of diseases and pathophysiological conditions. Advances in transition-metal-mediated cross-coupling have simplified
Fionn O'Hara et al.
Journal of the American Chemical Society, 135(32), 12122-12134 (2013-07-19)
Radical addition processes can be ideally suited for the direct functionalization of heteroaromatic bases, yet these processes are only sparsely used due to the perception of poor or unreliable control of regiochemistry. A systematic investigation of factors affecting the regiochemistry

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