3988-99-6

Usage

Synthesis Reference(s)

Tetrahedron, 21, p. 2413, 1965 DOI: 10.1016/S0040-4020(01)93897-9

InChI:InChI=1/C8H6S3/c1-3-7(9-5-1)11-8-4-2-6-10-8/h1-6H

Upstream product

• 7774-74-5 Thiophene-2-thiol 
• 74-86-2 acetylene 
• 96-43-5 2-thienyl chloride 
• 110-81-6 Diethyl disulfide 
• 51639-98-6 ethyldisulfanyl 
• 352-93-2 diethyl sulphide 
• 3600-24-6 diethyltrisulfane 
• 75-33-2 2-propanethiol 
• 75-08-1 ethanethiol 
• 33892-56-7 allyl(2-thiophene)sulfide 
• 3172-52-9 2,5-diclorothiophene 
• 2873-18-9 5-bromo-2-chlorothiophene 
• 7783-06-4 hydrogen sulfide 
• 3437-95-4 2-Iodothiophene 

Downstream Products

• 188290-36-0 thiophene 
• 7774-74-5 Thiophene-2-thiol 
• 7774-73-4 thiophene-3-thiol 
• 236-63-5 dithieno[2,3-b;3',2'-d]thiophene 
• 1386993-73-2 4-(4-fluorophenyl)-4H-dithieno[2,3-b:3',2'-e][1,4]thiazine 
• 1628813-13-7 4-(4-hexylphenyl)-4H-dithieno[2,3-b:3',2'-e][1,4]thiazine 

Relevant academic research and scientific papers

An efficient, one-pot and CuCl-catalyzed route to the synthesis of symmetric organic disulfides via domino reactions of thioacetamide and aryl (alkyl) halides

In this article, a simple, general and novel method for the synthesis of diaryl (dialkyl) disulfides from aryl (alkyl) halides is described. This is a convenient approach that involves the use of commercially available and inexpensive thioacetamide as a sulfur transfer reagent in the domino process for the synthesis of symmetric organic disulfides. Copyright

Gas-phase reaction of 2-chlorothiophene with hydrogen sulfide in the presence of alcohols

The effect of methanol and ethanol on the route of the gas-phase reaction of 2-chlorothiophene with hydrogen sulfide, leading to 2-thiophenethiol and to bis(2-thienyl) sulfide, has been investigated. It was found that methanol significantly enhances this

Reactions of Halothiophenes with Arene- and Hetarenethiols

Reactions of halothiophenes with sulfanyl radicals generated from arene- and hetarenethiols at 140-200°C have been studied for the first time. The reactions result in replacement of halogen in 2-bromothiophene and 2,5-dichloro-, 2-bromo-5-chloro-, and 2,5-dibromothiophenes. The two halogen atoms in dihalothiophenes are replaced only by phenylthio radical generated from benzenethiol. 4-Methylbenzenethiol and naphthalene-1-thiol react with halothiophenes most selectively, yielding corresponding unsymmetrical sulfides. The reactions with 2-thiophenethiol are accompanied by self-condensation to give dithienyl sulfide. The reactions of arene- and hetarenethiols with halothiophenes provide a synthetic route to unsymmetrical sulfides of the thiophene series, which are difficult to obtain by other methods, and allow prediction of the behavior of other sulfanyl radicals in similar reactions.

THERMAL TRANSFORMATIONS OF ALLYL 2-THIENYL SULFIDE AND SELENIDE

In the gas phase at 350-410 deg C allyl 2-thienyl sulfide is converted to thiophene-2-thiol, di(2-thienyl) sulfide, and 2-methylthienothiophene.In the presence of acetylene thienothiophene is formed in addition to these products.Allyl 2-thienyl selenide is converted quantitatively to 2,3-dihydro-2-methylselenophenothiophene during fractional distillation in vacuo.Thiophene, di(2-thienyl) selenide, di(2-thienyl) diselenide, thiophene-2-selenol, and 2-methylselenophenothiophene are formed in addition to these compounds in the thermolysis ofallyl thienyl selenide in the gas phase.In the presence of acetylene the thermal decomposition of allyl thienyl selenide is accompanied by the formation of selenophene.

FORMATION OF THIENOTHIOPHENES IN THE HIGH TEMPERATURE REACTION OF 2-CHLOROTHIOPHENE WITH COMPOUNDS CONTAINING THE C2H5S GROUP

The high temperature gas-phase reaction of 2-chlorothiophene with a mixture of diethyl disulfide and diethyl trisulfide constitutes a simple one-step synthesis of a 4:1 mixture of thioeno- and thieno-thiophenes.Their total yield depends on the nature of the donor of the ethylthio group.

NEW SYNTHESIS OF 1,2,5-SELENADIAZOLES

A new synthesis of 1,2,5-selenadiazoles which starts from unsubstituted or monosubstituted 1,2,5-thiadiazoles and Grignard reagents is described and the mechanism of the reaction discussed.

THERMAL HYDROTHIOLYSIS OF DI(2-THIENYL)SULFIDE IN THE GASEOUS AND LIQUID PHASE

At 500-600 deg C, di(2-thienyl)sulfide is converted to thiophene, thiophene thiols, dithienyls, and dithienothiophenes, and isomerized to 2,3-dithienylsulfide.Hydrogen sulfide accelerates these reactions significantly.In the liquid phase the thermal conversion of di(2-thienyl)sulfide takes place only with the participation of elemental sulfur or in the system sulfur-hydrogen sulfide.Thiophene and diethienothiophenes are not formed in this case, while isomerization occurs to a large degree.The observed thermal conversions of di(2-thienyl)sulfide are based on the addition of thiyl radicals to the double bonds of the thiophene ring and to the sulfide sulfur atom.