767840

Sigma-Aldrich

Zinc difluoromethanesulfinate

95%

Synonym(s):
Bis(((difluoromethyl)sulfinyl)oxy)zinc, DFMS, 1,1-difluoro-methanesulfinic acid zinc salt (2:1), Baran difluoromethylation reagent
Empirical Formula (Hill Notation):
C2H2F4O4S2Zn
CAS Number:
Molecular Weight:
295.55
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

95%

reaction suitability

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

reagent type: diversification reagent

storage temp.

2-8°C

SMILES string

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

InChI key

UGEYAPVLXKEKMP-UHFFFAOYSA-L

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General description

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.

Application

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.

Packaging

1, 10, 100 g in glass bottle

Linkage

Frequently Asked Questions are available for this Product.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
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...
Articles
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.
Read More

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