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767840

Sigma-Aldrich

Zinc difluoromethanesulfinate

95%

Sinônimo(s):

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 (Notação de Hill):
C2H2F4O4S2Zn
Número CAS:
1355729-38-2
Peso molecular:
295.55
Número MDL:
MFCD23134675
Código UNSPSC:
12352103
ID de substância PubChem:
329767342
NACRES:
NA.22

Nível de qualidade

100

Ensaio

95%

Formulário

solid

adequação da reação

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

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

UGEYAPVLXKEKMP-UHFFFAOYSA-L

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Descrição geral

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.

Aplicação

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.

Ligação

Frequently Asked Questions are available for this Product.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
MKCP2854
MKCH0947
MKBW4613V
MKBQ1358V
MKBQ0643V

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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
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
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
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

Artigos

Baran Diversinates™

The synthesis of heteroaromatic and aromatic compounds is at the heart of the chemical industry. The ever-growing demand for new chemical entities, coupled with dwindling resources and time constraints allotted to any given research project, a rapid way to diversify (hetero)aromatic scaffolds is needed.

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