247129-85-7

Basic information

• Product Name: (2-BroMoethyl)diphenylsulfoniuM TrifluoroMethanesulfonate
• Synonyms: (2-BroMoethyl)diphenylsulfoniuM TrifluoroMethanesulfonate;(2-Bromoethyl)diphenylsulfonium trifluoromethanesulfonate 97%;2-bromoethyl(diphenyl)sulfanium:trifluoromethanesulfonate
• CAS NO: 247129-85-7
• Molecular Formula: C15H14BrF3O3S2
• Molecular Weight: 443.2990696
• EINECS: -0
• Mol File: 247129-85-7.mol

Chemical Properties

• Melting Point: 88.0 to 92.0 °C
• Appearance: /
• CAS DataBase Reference: (2-BroMoethyl)diphenylsulfoniuM TrifluoroMethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (2-BroMoethyl)diphenylsulfoniuM TrifluoroMethanesulfonate(247129-85-7)
• EPA Substance Registry System: (2-BroMoethyl)diphenylsulfoniuM TrifluoroMethanesulfonate(247129-85-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 247129-85-7(Hazardous Substances Data)

Usage

Uses

Reactant for:Sulfinylation reactionsCyclization reactionsAnnulation reactions

Upstream product

• 139-66-2 diphenyl sulfide 
• 103935-47-3 2-bromoethyl triflate 

Downstream Products

• 1041173-22-1 methyl (3S)-4-[(4-methylphenyl)sulfonyl]morpholine-3-carboxylate 
• 1431756-37-4 (1S,2R,5R)-2-methyl-3-[(4-methylphenyl)sulfonyl]-6-oxa-3-azabicyclo[3.1.0]hexane 
• 1019853-17-8 (1S,2R,5R)-1,2-dimethyl-3-[(4-methylphenyl)sulfonyl]-6-oxa-3-azabicyclo[3.1.0]hexane 
• 1019853-21-4 1(S),2(S),5(R)-1a-ethyl-2-methyl-3-[(4-methylphenyl)sulfonyl]tetrahydro-1aH-oxireno[2,3-c]pyrrole 
• 1019853-20-3 1(S),2(R),5(R)-1a-ethyl-2-methyl-3-[(4-methylphenyl)sulfonyl]tetrahydro-1aH-oxireno[2,3-c]pyrrole 
• 1431756-54-5 (1S,2R,5R)-2-benzyl-1-ethyl-3-[(4-methylphenyl)sulfonyl]-6-oxa-3-azabicyclo[3.1.0]hexane 
• 1215006-78-2 (1S,3S,6R)-2,2-dimethyl-3-(4-nitrophenyl)-4,7-dioxabicyclo[4.1.0]heptane 

Relevant articles and documents

Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene

The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry of (hetero)cycles, N-vinylation of heterocyclic compounds, and palladium-catalyzed cross-coupling reactions. The structural features of the thianthrene core enable a distinct synthesis and reactivity profile, unprecedented for other vinyl sulfonium derivatives.

Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate

The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.

Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: Synthesis of dihydrofuran derivatives

A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.

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A convenient cyclopropanation process of oxindoles via bromoethylsulfonium salt

A practical convenient conversion of oxindoles into the corresponding spirocyclopropyl oxindoles is achieved efficiently using bromoethylsulfonium salt, which is easily prepared on a large scale and is stable crystalline. This reaction of bromoethylsulfonium salt with different substituted unprotected oxindoles proceeded under mild condition and provided moderate yields.

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An efficient and practical synthesis of 2′,3′-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.

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