6007-71-2

Usage

Uses

Used in Solvent Applications:
2-methyl-2,5-dihydrothiophene 1,1-dioxide is utilized as a solvent for its ability to dissolve a range of substances, facilitating various chemical processes and reactions.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 2-methyl-2,5-dihydrothiophene 1,1-dioxide is employed as a key component in the production of medications, leveraging its chemical properties to contribute to the efficacy and formulation of drugs.
Used as a Building Block in Chemical Production:
2-methyl-2,5-dihydrothiophene 1,1-dioxide serves as a fundamental building block in the synthesis of other chemicals, underpinning the creation of a variety of products in the chemical industry.
Used in Organic Chemistry and Material Science:
2-methyl-2,5-dihydrothiophene 1,1-dioxide is harnessed in the synthesis of various organic compounds, playing a crucial role in advancing research and development within the fields of organic chemistry and material science.
Used in Chemical Synthesis:
As a versatile intermediate, 2-methyl-2,5-dihydrothiophene 1,1-dioxide is used in the synthesis of a multitude of organic compounds, contributing to the diversity of chemical products available.
Safety Note:
Given its flammable nature, 2-methyl-2,5-dihydrothiophene 1,1-dioxide requires careful handling and should be stored in a well-ventilated area to mitigate risks associated with its chemical properties.

Upstream product

• 2004-70-8 1-methylbuta-1,3-diene 
• 77-79-2 3-Sulfolene 
• 74-88-4 methyl iodide 
• 53336-42-8 3-bromo-2,3-dihydro-thiophene-1,1-dioxide 
• 61464-28-6 2-methyl-4,5-dihydrothiophene 1,1-dioxide 
• 106212-24-2 (+/-)-2,5-dihydro-2-(trimethylsilyl)thiophene 1,1-dioxide 

Downstream Products

• 30293-90-4 4-methyl-3a,4,6,6a-tetrahydro-3H-thieno[3,4-c]pyrazole 5,5-dioxide 
• 30293-89-1 6-methyl-3a,4,6,6a-tetrahydro-3H-thieno[3,4-c]pyrazole 5,5-dioxide 
• 54795-49-2 (+/-)-3c-methyl-cyclohex-4-ene-1r,2c-dicarboxylic acid dimethyl ester 
• 106212-25-3 2-methyl-5-(trimethylsilyl)-3-sulfolene 
• 61464-28-6 2-methyl-4,5-dihydrothiophene 1,1-dioxide 
• 109-68-2 2-pentene 
• 375-81-5 perfluoro-n-pentane sulfonylfluoride 
• 28084-22-2 perfluoromethylbutane sulfonylfluoride 

Relevant academic research and scientific papers

A Study of 2-Methyl-3-phenylsulphinyl-2,3,4,5-tetrahydrothiophene 1,1-Dioxides: NMR Spectra, Crystal Structure and Dehydrosulphinylations

The (2R*,3S*,SR*) and (2R*,3S*,SS*) isomers of 2-methyl-3-phenylsulphinyl-2,3,4,5-tetrahydrothiophene 1,1-dioxide were converted to 2-methyl-4,5-dihydrothiophene 1,1-dioxide in refluxing toluene, while the (2S*,3S*,SR*) isomer underwent thermolysis to give 2-methyl-2,5-dihydrothiophene 1,1-dioxide.No reaction of the (2S*,3S*,SS*) isomer occurred because the required conformation in dehydrosulphinylation was prohibited by the steric effect of the methyl and phenyl groups.

4-Bromo-2-sulfolenes. Butadienyl Cation Equivalents

4-Bromo-2-sulfolene and 4-bromo-3-methyl-2-sulfolene react with alkylcuprates to give direct substitution products, with vinyl- or phenylcuprates or sulfur-containing nucleophiles to give allylic substitution products, and with strongly basic nucleophiles to give elimination products.The allylic substitution products and the isomerized direct substitution products are precursors for substituted 1,3-butadienes.Thus, these 4-bromo-2-sulfolenes serve as butadienyl cation equivalents.

Control of Regioselectivity in the Alkylation of 2-Trimethylsilyl-2,5-dihydrothiophene 1,1-Dioxide. A Route for 2,2-Dialkylation

The readily available 2-trimethylsilyl-2,5-dihydrothiophene 1,1-dioxide can be converted regioselectively into the dialkyl- and dispiro analogues, which are precursors of the corresponding 1,1-disubstituted buta-1,3-dienes and asymmetric dicycloalkylidenylethanes, respectively.

Stereoselective Synthesis of (E)-, (E,Z)-, and (E,E)-Conjugated Dienes via Alkylation of 3-Sulfolenes as the Key Step

A new stereoselective method is presented for synthesizing (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step.Direct alkylation of 3-sulfolene at the 2-position proceeds with good yields when labile sulfolene α-carbanion is generated in the presence of alkyl iodides in THF-HMPA solution at -78 deg C.Alkylation of 2-alkyl-3-sulfolenes gives trans-2,5-dialkyl-3-sulfolenes with 100percent regioselectivity and more than 90percent stereoselectivity.Desulfonylation of trans-3,5-disubstituted 3-sulfolenes is examined in detail, and the conditions to give stereoselectively the corresponding (E,Z)-and (E,E)-conjugated dienes are found.Applying the method, three insect pheromones, (E)-9,11-dodecadien-1-yl acetate, a sex pheromone of the red bollworm moth, (E,E)-8,10-dodecadien-1-ol, a sex pheromone of the codling moth, and (E,E)-11,13-hexadecadienal, a sex pheromone of the cabbage webworm, are easily synthesized by starting with 3-sulfolene with nearly 100percent stereoselectivity.Synthesis of cis-3,4,5-trisubstituted cyclohexenes using 2-substituted 3-sulfolenes as the diene synthons is also described.

One-Pot Sequential Acylation/Alkylation Reactions of 3-Sulfolenes

3-Sulfolene 2-anion and 3-methyl-3-sulfolene 2-anion have been generated at -105 deg C and are stable in the absence of electrophiles for at least 15 min at this temperature.These anions were used in sequential reactions with acyl chlorides and alkyl halides to yield the corresponding 2-acyl-2-alkyl-3-sulfolenes.

Study of the Alkylation Reactions of Sulphol-3-enes

Sulphol-3-ene can be deprotonated with sodium hydride in DMF to form the α-anion which reacts with various alkyl halides to give the 2-alkylsulpholenes.This approach provides a regiospecific preparation of disubstituted sulphol-3-enes and sulphol-2-enes.

STEREOSELECTIVE SYNTHESIS OF (E)-, (E,Z)- AND (E,E)-CONJUGATED DIENES VIA ALKYLATION OF 3-SULFOLENES AS KEY STEP

Stereoselective method for synthesizing (E)-, (E,Z)- and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as key step is developed.Sex pheromones with (E)- and (E,E)-conjugated diene structures are synthesized with exclusively high stereoselectivity by applying the method.