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Sigma-Aldrich

Zinc difluoromethanesulfinate

95%

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C2H2F4O4S2Zn
Numero CAS:
Peso molecolare:
295.55
Numero MDL:
Codice UNSPSC:
12352103
ID PubChem:
NACRES:
NA.22
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Livello qualitativo

Saggio

95%

Stato

solid

Impiego in reazioni chimiche

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

reagent type: diversification reagent

Gruppo funzionale

fluoro
sulfinic acid

Temperatura di conservazione

2-8°C

Stringa SMILE

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
UGEYAPVLXKEKMP-UHFFFAOYSA-L

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Descrizione generale

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.[1]

Applicazioni

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.

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Frequently Asked Questions are available for this Product.

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°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

Articoli

Rapidly diversify (hetero)aromatic scaffolds for chemical industry needs amid resource and time constraints, ensuring efficiency.

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