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CF0014

Sigma-Aldrich

Phenylsulfanyltetrafluorobromoethane

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About This Item

Linear Formula:
C8H5BrF4S
CAS Number:
83015-33-2
MDL number:
MFCD27996155
UNSPSC Code:
12352101
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: C-C Bond Formation

Application

Phenylsulfanyltetrafluoroethyl bromide is a fluoroalkylbromide that is a radical source of the phenylsulfanyltetrafluoroethyl moiety. Alternatively, it can also be selectively metallated at the fluorinated carbon with Turbo Grignard reagent at low temperatures resulting in a thermally unstable anion that can act as a nucleophilic fluoroalkylation reagent towards a wide variety of electrophiles, such as aldehydes, ketones or sulfonylimines. A phenylsulfanyltetrafluoroethyl moiety incorporated in the substrate can be treated with tributyltin hydride and generate the corresponding fluoroalkyl radical. If the substrate lacks any olefins, it can be reduced to tetrafluoroethyl group whereas if the substrate contains an olefin in a correct spatial orientation, it can lead to an intramolecular cyclization affording tetrafluorinated cyclic structures.

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Other Notes

Technology Spotlight: Fluoroalkylation: Expansion of Togni Reagents

Legal Information

Product of CF Plus Chemicals.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319,H413

Precautionary Statements

P273 - P305 + P351 + P338

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Articles

Fluoroalkylation: Expansion of Togni Reagents

The fluoroalkylation toolbox now includes Togni reagents, hypervalent iodine perfluoroalkylation reagents, fluoroalkyl bromides, silanes, carboxylates, and sulfonyl fluorides for late stage fluoroalkylation.

Fluoroalkylation: Expansion of Togni Reagents

The fluoroalkylation toolbox now includes Togni reagents, hypervalent iodine perfluoroalkylation reagents, fluoroalkyl bromides, silanes, carboxylates, and sulfonyl fluorides for late stage fluoroalkylation.

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