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Usage

Uses

Used in Pharmaceutical Synthesis:
3-Bromotetrahydrothiophene 1,1-dioxide is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of new molecules with potential biological activity, making it a valuable component in drug discovery and development processes.
Used in Agrochemical Synthesis:
In the agrochemical industry, 3-Bromotetrahydrothiophene 1,1-dioxide serves as a crucial building block for the synthesis of compounds with pesticidal properties. Its heterocyclic nature and reactivity contribute to the development of effective and novel agrochemicals.
Used in Organic Synthesis Research:
3-Bromotetrahydrothiophene 1,1-dioxide is also employed in academic and research settings for the study of reaction mechanisms. Its unique structure provides opportunities to explore new synthetic methodologies and understand the underlying chemical processes in organic synthesis.
Used in the Development of New Molecules:
Due to its potential as a starting material, 3-Bromotetrahydrothiophene 1,1-dioxide is used in the development of new molecules with applications in various fields. Its versatility in organic synthesis allows for the creation of a wide range of compounds with different properties and uses.

InChI:InChI=1/C4H7BrO2S/c5-4-1-2-8(6,7)3-4/h4H,1-3H2

Upstream product

• 39013-66-6 3-bromotetrahydrothiophene 
• 62266-25-5 benzyl but-3-enyl sulfide 

Downstream Products

• 1233526-31-2 Racemic 1-(1,1-dioxidotetrahydrothiophen-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 1192-16-1 2,3-dihydrothiophene-1,1-dioxide 

Relevant academic research and scientific papers

Regiochemical and Stereochemical Studies on Halocyclization Reactions of Unsaturated Sulfides

The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent.Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts.The endo- versus exo-regioselectivity of these alkenyl sulfide ring closure most likely reflects the difference in thermodynamic stabilities of the β-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate.The efficiency of cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers.Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides.Conversely, the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length.Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring.The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control.The methodology has been applied to the synthesis of unusual bicyclic β-lactams related to the penicillin family of antibiotics.

Regiochemical Studies on Halocyclization Reactions of Unsaturated Sulfides

The regiochemistry of halocyclization reactions for olefinic and acetylenic sulfides has been examined.Key words: Electrophilic cyclizations, halocyclizations, sulfur cyclizations, unsaturated sulfides, halosulfones