16587-52-3

Usage

Uses

Used in Environmental Remediation:
3-METHYLDIBENZOTHIOPHENE is used as a target compound for biodegradation in the development of methods to remove spilled oil from marine and terrestrial environments. The application reason is that certain bacteria have the ability to break down 3-METHYLDIBENZOTHIOPHENE, along with other harmful PAHs, which can help in cleaning up oil spills and reducing their environmental impact.
Used in Crude Oil Processing:
3-METHYLDIBENZOTHIOPHENE is used as a component in crude oil, which is a significant source of energy and raw material for various industries. The application reason is that its presence in crude oil affects the refining process and the quality of the final products, making it an important factor to consider in the oil industry.

InChI:InChI=1/C13H10S/c1-9-6-7-11-10-4-2-3-5-12(10)14-13(11)8-9/h2-8H,1H3

Upstream product

• 97511-04-1 2-bromodibenzo[b,d]thiophene 
• 77-78-1 dimethyl sulfate 
• 113222-82-5 3-Methyldibenzothiophen-5,5-dioxid 
• 128916-13-2 2-Allylsulfanyl-benzoic acid p-tolyl ester 
• 119303-10-5 7-methyl-11H-dibenz<1,4>-oxathiepin-11-one 
• 144463-76-3 allyl 2-(3-methylthiophenoxy)benzoate 
• 16587-53-4 7-methyl-1,2,3,4-tetrahydro-dibenzothiophene 
• 128916-15-4 2-Allylsulfanyl-benzoic acid m-tolyl ester 
• 37692-09-4 4-methyl-2-phenylsulfanylaniline 
• 6320-03-2 2-chlorothiphenol 
• 5720-05-8 4-methylphenylboronic acid 
• 6320-02-1 o-bromothiophenol 
• 108-40-7 toluene-3-thiol 
• 583-55-1 1-Bromo-2-iodobenzene 

Relevant academic research and scientific papers

Synthesis and properties of thieno[2,3-d:5,4-d']bisthiazoles and their oxidized derivatives: Thionyl chloride as a sulfurative ring-fusing reagent towards thiophene-based ring-fused heteroaromatic compounds

A new route to thiophene-ring-fused compounds with thionyl chloride as a sulfur source was developed. Use of an excess amount thionyl chloride directly gave the corresponding thiophene-ring-fused compound via further reduction of generated thiophene-S-oxide with excess thionyl chloride in some cases. One-pot reduction with tributylphosphine also gave thiophene-ring-fused compounds in good yields, and oxidation with NaClO·5H2O gave S-dioxides. In addition, one of the obtained thiazole-thiophene ring-fused compounds showed some unexpected mechanochromism behavior.

Synthesis method of substituted dibenzothiophene compound

The invention belongs to the technical field of organic synthesis, and particularly discloses a synthesis method of a substituted dibenzothiophene compound. The method comprises the following steps: reacting halogenated substituted biphenyl with an organic strong base at a low temperature, reacting with ethanedithiol to obtain a high-purity key intermediate mercaptobiphenyl, and carrying out a coupling reaction under the action of a catalyst to obtain the substituted dibenzothiophene compound. The method provided by the invention has the advantages of low raw material cost, mild reaction conditions, short reaction time, simple post-treatment, single reaction product, few byproducts, no impurity difficult to remove, simple process operation, easy obtaining of high-purity products, suitability for large-scale production of the process and the like.

Synthesis of Benzo[b]thiophenes through Rhodium-Catalyzed Three-Component Reaction using Elemental Sulfur

A benzo[b]thiophene synthesis by Rh-catalyzed three-component coupling reaction of arylboronic acids, alkynes, and elemental sulfur (S8) is developed. A notable feature of this protocol is that the thienannulation (thiophene annulation) proceeds with high regioselectivity via the sequential alkyne insertion, C?H activation, and then sulfur atom transfer to the metallacycle intermediate. In a similar manner, dibenzothiophenes can be synthesized from the parent biarylboronic acids and S8. (Figure presented.).

A Pd-catalyzed optional approach for the synthesis of dibenzothiophenes

A direct and practical approach for the construction of DBTs was developed via a Pd-catalyzed tandem reaction, in which commercially available o-bromo-iodobenzenes combined with benzene thiols or iodobenzenes combined with o-bromo-benzene thiols were applied. These two approaches will provide an alternative for the synthesis of DBT derivatives.

Palladium catalysis based one-pot synthesis method for DBTs (dibenzothiophenes)

The invention discloses a palladium catalysis based one-pot synthesis method for DBTs (dibenzothiophenes). An inorganic base is added to an N,N-dimethylacetamide solution, with a palladium catalyst/ligand as a catalysis system, o-bromoiodobenzene derivatives or iodobenzene derivatives and thiophenol derivatives taken as raw materials are subjected to a reaction in nitrogen atmosphere, and DBTs areobtained through separation. The simple, economical and easily available raw materials are taken as substrates, all-position-substituted DBTs are synthesized on the basis of palladium catalyzed cascade reaction, and DBTs have great application prospect in medical synthesis intermediates and organic optoelectronic material science.

Cyclization of 2-Biphenylthiols to Dibenzothiophenes under PdCl2/DMSO Catalysis

A palladium-catalyzed synthesis of dibenzothiophenes from 2-biphenylthiols is described. This highly efficient reaction employs a simple PdCl2/DMSO catalytic system, in which PdCl2 is the sole metal catalyst and DMSO functions as an oxidant and solvent. This transformation has broad substrate scope and operational simplicity and proceeds in high yield. The synthetic utility was demonstrated by the facile synthesis of helical dinapthothiophene 3 and an eminent organic semiconductor DBTDT 4. Importantly, highly strained trithiasumanene 5, a buckybowl of considerable synthetic challenge, was observed under this catalytic system.

Palladium(II)-Catalyzed Synthesis of Dibenzothiophenes from 2-Biphenylyl Disulfides by C?H Functionalization

The palladium-catalyzed oxidative preparation of dibenzothiophene derivatives from 2-biphenylyl disulfides by C?H functionalization is described herein. This procedure shows a high tolerance toward various functional groups and does not require the further addition of a metal oxidant, a base, or a ligand. Also, the present method was applied to the facile preparation of dibenzoselenophene.

Green Preparation of Dibenzothiophene Derivatives Using 2-Biphenylyl Disulfides in the Presence of Molecular Iodine and Its Application to Dibenzoselenophene Synthesis

A protocol for the direct preparation of dibenzothiophenes from 2-biarylyl disulfides in the presence of an economic and ecological oxidant, molecular iodine, was explored. This protocol was used for the direct preparation of dibenzoselenophene.

Iron-catalyzed carbon–sulfur bond formation: Atom-economic construction of thioethers with diaryliodonium salts

Diaryliodonium salts are characterized by poor atom economy with the formation of one equivalent of an iodoarene as waste. We have developed an atom-economic iron-catalyzed protocol for the synthesis of a variety of thioethers with diaryliodonium salts. Not only cyclic diaryliodonium salts but also linear diaryliodonium salts were found to perform well in the reactions.

N-Benzyldithiocarbamate Salts as Sulfur Sources to Access Tricyclic Thioheterocycles Mediated by Copper Species

Using an easily prepared triethylammonium N-benzyldithiocarbamate salt as a sulfur source, a dual C?S functionalization of cyclic diaryliodoniums to form tricyclic thioheterocycles is realized. Our method uses the readily available copper sulfate to accelerate the chemical transformation under mild conditions. A broad range of cyclic diaryliodoniums with a ring size from 5- to 7-membered can be employed to gain a quick access to tricyclic thioheterocycles including dibenzothiophenes, thioxanthenes, and phenoxathiines. (Figure presented.).