18214-56-7

Usage

Uses

Used in Pharmaceutical Industry:
3,4-dimethyl-2,5-dihydrothiophene 1,1-dioxide is used as a solvent or intermediate for the synthesis of various pharmaceutical compounds.
Used in Agrochemical Industry:
3,4-dimethyl-2,5-dihydrothiophene 1,1-dioxide is used as a solvent or intermediate for the synthesis of various agrochemical compounds.
Used in Polymer Industry:
3,4-dimethyl-2,5-dihydrothiophene 1,1-dioxide is used as a solvent or intermediate for the synthesis of various polymer compounds.
Used in Industrial Applications:
3,4-dimethyl-2,5-dihydrothiophene 1,1-dioxide is used as a solvent or intermediate in various industrial applications due to its wide range of uses and relatively stable and non-reactive nature under normal conditions.
However, it should be handled with care due to its potential health hazards, including skin and eye irritation, and it should be used in a well-ventilated area with appropriate protective equipment.

Upstream product

• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 114079-03-7 3-bromo-3,4-dimethyl-2,3-dihydro-thiophene-1,1-dioxide 
• 127844-21-7 3-Benzenesulfonyl-3,4-dimethyl-2,3-dihydro-thiophene 1,1-dioxide 
• 98194-64-0 Diethyl-thioxomalonat-S-oxid 
• 80043-96-5 3,4-dibromo-3,4-dimethyltetrahydrothiophene-1,1-dioxide 
• 64-19-7 acetic acid 
• 67-64-1 acetone 
• 52722-92-6 3,3'-sulfonylbis(2-methylprop-1-ene) 
• 114596-87-1 3-methyl-4-(phenylsulfonyl)-3-sulfolene 
• 1228075-04-4 4,4'-sulfonylbis(2-methylbut-1-ene) 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 93604-54-7 3-methyl-4-(phenylthio)-2,5-dihydrothiophene 1,1-dioxide 
• 73617-41-1 3,4-dimethyl-2,3-dihydro-thiophene-1,1-dioxide 

Downstream Products

• 1003-82-3 3,4-Dimethyl-sulfolan 
• 80043-96-5 3,4-dibromo-3,4-dimethyltetrahydrothiophene-1,1-dioxide 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 18214-57-8 3,4-bis-(bromomethyl)-2,5-dihydrothiophene 1,1-dioxide 
• 381725-24-2 [4-(4-nitro-phenoxycarbonylmethylsulfanylmethyl)-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-3-ylmethylsulfanyl]-acetic acid 4-nitro-phenyl ester 
• 132869-39-7 (1S,2S,6R,7R)-8,9-Dimethylene-4-phenyl-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione 
• 132869-44-4 6-Phenyl-4,4a,7a,8-tetrahydro-furo[3,4-f]isoindole-5,7-dione 
• 132869-41-1 N,N'-Diphenyl-1,4-epoxy-1,2,3,4,5,6,7,8-octahydronaphthalene-2-exo,3-exo-6,7-tetracarboximide 
• 28084-25-5 perfluoro-3,4-dimethyl-butanesulfonylfluoride 
• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 375-81-5 perfluoro-n-pentane sulfonylfluoride 

Relevant academic research and scientific papers

Solvent effect in pericyclic reactions. X. The cheletropic reaction

The effect of the solvent on the cheletropic reaction of 3,4-dimethyl-2,5-dihydrothiophen-1,1-dioxide was kinetically investigated in 14 solvents. The rate constants of the forward reaction as well as those of the reverse process and the corresponding equilibrium constants were found to be linearly correlated with the E(T)(30) solvent polarity parameters. The solvent effect can be interpreted in terms of change of polarity during the activation process. The different response of the forward and reverse process to the increase of solvent polarity pointed out a clear difference between pericyclic reactions characterized by non-specific solvent effects and those whose medium effect is determined by the specific interaction between the FMO of solute and solvent.

Crystal Structure Analysis of 3,4-Dimethyl-2,5-dihydrothiophen-1,1-dioxide

The geometry of 3,4-dimethyl-2,5-dihydrothiophen-1,1-dioxide was determined by X-ray diffraction: cell dimensions are reported together with bond lengths and bond angles.While bond lengths are smaller than those for the homologue 3-methyl-2,5-dihydrothiophen-1,1-dioxide, bond angles are similar.The Me-C3-C4-Me torsion angle is 5.1 +/- 0.5 deg.The results are consistent with its relatively slow rate of decomposition. - Keywords: X-Ray analysis

THE VOLUME PROFILE FOR A CHELETROPIC REACTION

The volumes of activation and of reaction were measured for the reaction between sulphur dioxide and 2,3-dimethyl-buta-1,3-diene to form 3,4-dimethylsulpholene.Values of ΔV and ΔV* are -33 and -35 cm3/mol, respectively in accordance with a concerted reaction having a very product-like transition state.

Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent

We present herein an efficient and practical method for a gram scale synthesis of 3-sulfolenes using sodium metabisulfite as a safe, inexpensive, and easy to handle sulfur dioxide equivalent. Diversely-substituted 3-sulfolenes can be prepared by reacting a variety of 1,3-dienes or allylic alcohols with sodium metabisulfite in aqueous hexafluoroisopropanol (HFIP) or in aqueous methanol in the presence of potassium hydrogen sulfate. Advantageously, the method enables conversion of allylic alcohols directly to 3-sulfolenes, bypassing intermediate 1,3-dienes.

Diversity oriented approach to phenylalanine derivatives via the dielsalder reaction involving sulfolene intermediates

We report a new synthetic approach to highly functionalized phenylalanine derivatives via sulfolenes as latent diene equivalents. Here, the DielsAlder reaction has been used as a key step to assemble diverse unusual amino acid derivatives.

Stoichiometric release of SO2 from adducts: Application to the direct synthesis of protected dienes

Abstract The in situ, stoichiometric release of SO2 was studied from DABSO (DABCO adduct with SO2) and DMAP adduct. When involved in cheletropic additions, free SO2 released by this technique proved much more reactive than its adducts. Some examples of applications towards the direct synthesis of protected dienes from allylic alcohols are given.

2-PHENYL-5-HETEROCYCLYL-TETRAHYDRO-2H-PYRAN-3-AMINE COMPOUNDS FOR USE IN THE TREATMENT OF DIABETES AND ITS ASSOCIATED DISORDERS

The present invention relates to novel compounds of the general formula (I) their tautomeric forms, their enantiomers, their diastereoisomers, their pharmaceutically accepted salts, or pro-drugs thereof, which are useful for the treatment or prevention of diabetes mellitus (DM), obesity and other metabolic disorders. The invention also relates to process for the manufacture of said compounds, and pharmaceutical compositions containing them and their use.

DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.

Synthesis and RCM activity of [(NHC)(NHCewg)RuCl 2(3-phenylindenylid-1-ene)] complexes

[(NHC)RuCl2(3-phenylindenylid-1-ene)(py)] (1) serves as a convenient starting material for the synthesis of [(NHC)(NHCewg) RuCl2(3-phenylindenylid-1-ene)] complexes 3a-3g utilizing [AgI(NHCewg)] complexes (2) as NHC transfer reagents. The respective complexes 3 display excellent activities in RCM reactions leading to tetrasubstituted olefins. The most active precatalyst, 3f, is characterized by 3,4-dichloro and N,N′-diethyl substituents and can be obtained in 94% isolated yield. The redox potentials of complexes 3 and the crystal structure of 3g (3,4-dichloro and N,N′-diisopropyl substituents) were determined.

[(NHC)(NHCewg)RuCl2(CHPh)] complexes with modified NHCewg ligands for efficient ring-closing metathesis leading to tetrasubstituted olefins

Imidazolium salts (NHCewg-HCl) with electronically variable substituents in the 4,5-position (H,H or C1,C1 or H,NO2 or CN 5CN) and sterically variable substituents in the 1,3-position (Me,Me or Et,Et or iPr,iPr or Me,iPr) were synthesized and converted into the respective [AgI(NHC)ewg] complexes. The reactions of [(NHC)RuCl 2(CHPh)(Py)2] with the [AgI(NHQw8)] complexes provide the respective [(NHC)(NHCewg)RuCl2(CHPh)] complexes in excellent yields. The catalytic activity of such complexes in ring-closing metathesis (RCM) reactions leading to tetrasubstituted olefins was studied. To obtain quantitative substrate conversion, catalyst loadings of 0.2-0.5 mol% at 80°C in toluene are sufficient. The complex with the best catalytic activity in such RCM reactions and the fastest initiation rate has an NHCewg group with l,3-Me,iPr and 4,5-Cl,Cl substituents and can be synthesized in 95 % isolated yield from the ruthenium precursor. To learn which one of the two NHC ligands acts as the leaving group in olefin metathesis reactions two complexes, [(FL-NHC)-(NHCcwg)RuCl2(CHPh)] and [(FLNHCewg)(NHC)RuCl2(CHPh)], with a dansyl fluorophore (FL)-tagged electron-rich NHC ligand (FL-NHC) and an electron-deficient NHC ligand (FLNHCewg) were prepared. The fluorescence of the dansyl fluorophore is quenched as long as it is in close vicinity to ruthenium, but increases strongly upon dissociation of the respective fluorophore-tagged ligand. In this manner, it was shown for ring-opening metathesis ploymerization (ROMP) reactions at room temperature that the NHCewg ligand normally acts as the leaving group, whereas the other NHC ligand remains ligated to ruthenium.