3886-39-3

Basic information

• Product Name: 2,3-Benzodithiin,1,4-dihydro-
• Synonyms: 2,3-Benzodithian(7CI,8CI); RD 3-0028
• CAS NO: 3886-39-3
• Molecular Formula: C8H8 S2
• Molecular Weight: 168.284
• Mol File: 3886-39-3.mol

Chemical Properties

• CAS DataBase Reference: 2,3-Benzodithiin,1,4-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Benzodithiin,1,4-dihydro-(3886-39-3)
• EPA Substance Registry System: 2,3-Benzodithiin,1,4-dihydro-(3886-39-3)

Safety Data

• Hazardous Substances Data: 3886-39-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Benzodithiin,1,4-dihydrois utilized as a key intermediate in the synthesis of pharmaceuticals due to its unique structure and reactivity. Its sulfur-containing ring provides a distinct pharmacophore that can be exploited for the development of novel therapeutic agents with potential applications in treating various diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 2,3-Benzodithiin,1,4-dihydroserves as a crucial building block for the creation of new agrochemicals. Its properties allow for the design of innovative compounds with improved efficacy and selectivity in crop protection and pest management.
Used in Organic Synthesis:
2,3-Benzodithiin,1,4-dihydrois employed as a versatile starting material in organic synthesis. Its sulfur-containing ring and aromatic nature make it an attractive candidate for the preparation of a wide range of organic compounds, including specialty chemicals, dyes, and other functional materials.
Overall, 2,3-Benzodithiin,1,4-dihydrois a significant chemical compound with diverse applications across different industries, primarily due to its unique structural features and reactivity. Its potential in pharmaceuticals, agrochemicals, and organic synthesis highlights its importance in the development of new and improved products.

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Relevant articles and documents

Synthesis of cyclic disulfides using didecyldimethylammonium bromide as phase transfer catalyst

A convenient, practical and general method for the synthesis of symmetrical and unsymmetrical cyclic disulfides based on the reaction of sulfur with sodium sulfide in the presence of didecyldimethylammonium bromide (DDAB) as a phase transfer catalyst is described.

Facile Construction of Yttrium Pentasulfides from Yttrium Alkyl Precursors: Synthesis, Mechanism, and Reactivity

Treatment of the yttrium dialkyl complex TpMe2Y(CH2Ph)2(THF) (TpMe2 = tri(3,5 dimethylpyrazolyl)borate, THF = tetrahydrofuran) with S8 in a 1:1 molar ratio in THF at room temperature afforded a yttrium pentasulfide TpMe2Y(κ4-S5) (THF) (1) in 93% yield. The yttrium monoalkyl complex TpMe2CpYCH2Ph(THF) reacted with S8 in a 1:0.5 molar ratio under the same conditions to give another yttrium pentasulfide [(TpMe2)2Y]+[Cp2Y(κ4-S5)]? (10) in low yield. Further investigations indicated that the S52- anion facilely turned into the corresponding thioethers or organic disulfides, and released the redundant S8, when it reacted with some electrophilic reagents. The mechanism for the formation of the S52- ligand has been investigated by the controlling of the reaction stoichiometric ratios and the stepwise reactions.

Enzyme-catalysed oxidation of 1,2-disulfides to yield chiral thiosulfinate, sulfoxide and cis-dihydrodiol metabolites

Enantioenriched and enantiopure thiosulfinates were obtained by asymmetric sulfoxidation of cyclic 1,2-disulfides, using chemical and enzymatic (peroxidase, monooxygenase, dioxygenase) oxidation methods and chiral stationary phase HPLC resolution of racemic thiosulfinates. Enantiomeric excess values, absolute configurations and configurational stabilities of chiral thiosulfinates were determined. Methyl phenyl sulfoxide, benzo[c]thiophene cis-4,5-dihydrodiol and 1,3-dihydrobenzo[c]thiophene derivatives were among unexpected types of metabolites isolated, when acyclic and cyclic 1,2-disulfide were used as substrates for Pseudomonas putida strains. Possible biosynthetic pathways are presented for the production of metabolites from 1,4-dihydrobenzo-2,3-dithiane, including a novel cis-dihydrodiol metabolite that was also derived from benzo[c]thiophene and 1,3-dihydrobenzo[c]thiophene.

Stereoselective reductase-catalysed deoxygenation of sulfoxides in aerobic and anaerobic bacteria.

Direct and indirect evidence, of unexpected stereoselective reductase-catalysed deoxygenations of sulfoxides, was found. The deoxygenations proceeded simultaneously, with the expected dioxygenase-catalysed asymmetric sulfoxidation of sulfides, during some biotransformations with the aerobic bacterium Pseudomonas putida UV4. Stereoselective reductase-catalysed asymmetric deoxygenation of racemic alkylaryl, dialkyl and phenolic sulfoxides was observed, without evidence of the reverse sulfoxidation reaction, using anaerobic bacterial strains. A purified dimethyl sulfoxide reductase, obtained from the intact cells of the anaerobic bacterium Citrobacter braakii DMSO 11, yielded, from the corresponding racemates, enantiopure alkylaryl sulfoxide and thiosulfinate samples.

Reduction of sulfur with borohydride exchange resin in methanol: Application to rapid and selective synthesis of disulfides

A convenient and rapid method for the synthesis of symmetrical disulfides from alkyl or aryl alkyl halides using sulfurated borohydride exchange resin (SBER) under anhydrous conditions is described. Selective transfer of sulfur to an alkyl group rather than an aryl group is achieved using this methodology.

Antiviral agent containing benzodithiin derivative as active ingredient

Antiviral agents comprising, as an active ingredient, a 1,4-dihydro-2,3-benzodithiin derivative of the formula STR1 wherein each symbol is as defined in the Specification, or a pharmacologically acceptable salt thereof. The antiviral agents of the present invention have superior antiviral activity and are effective for the preventive and therapeutic treatment of viral diseases caused typically by RS virus.

Reductive Dimerization of Organic Thiocyanates to Disulfides Mediated by Tetrathiomolybdate

An interesting reductive dimerization of organic thiocyanates assisted by benzyltriethylammonium tetrathiomolybdate, , 1, leads to the formation of the corresponding disulfides in high yields.

An Investigation of the Retro Diels-Alder Reaction as a Method for the Generation of Diatomic Sulfur

The cyclic disulfides 2,3-dithiabicyclooct-5-ene 5, 1,4-dihydro-2,3-benzodithin 6 and hexahydro-5,8-epoxy-2,3-benzodithiin 7 have been prepared by oxidation of the corresponding dithiols.Each of these compounds has been subjected to vapour phase pyrolysis in order to determine whether a retro Diels-Alder reaction occurs, leading to the formation of diatomic sulfur (S2) and a diene.Compounds 5 and 7 both appeared to decompose in this way; in each case the expected diene was detected in the pyrolysate together with sulfur (S8).Attempts to intercept S2 and thus to obtain direct evidence for its formation were not successful.The benzodithiin 6 underwent an analogous loss of sulfur on vapour phase pyrolysis, but only as a minor reaction pathway, and this decomposition pathway was not detectable in solution pyrolyses.Solution pyrolysis of 6 in the presence of N-phenylmaleinimide gave N-phenyl-2,3-naphthalimide 21 in low yield. cis-Cyclopentene-3,5-dithiol 9 has also been prepared but no evidence could be obtained for the formation of disulfide 4 on oxidation.Reaction of the dithiol 9 with aldehydes and ketones in the presence of acids led to the formation of adducts (such as 12 and 13 from acetone) which were rapidly interconverted in acidic media.

Investigation of a transition metal-assisted retro Diels-Alder reaction used in the synthesis of transition metal S2O complexes

Treatment of 4,5-diphenyl-3,6-dihydro-1,2-dithiin-1-oxide with coordinatively unsaturated transition metal complexes resulted in the production of S2O complexes and 2,3-diphenylbutadiene.A transition metal-assisted retro Diels-Alder mechanism has been proposed for this reaction.A series of IR and 1H NMR experiments and MNDO calculations on 4,5-diphenyl-3,6-dihydro-1,2-dithiin-1-oxide have been performed to gain additional information about this transformation.