4923-91-5

Usage

Uses

Used in Fuel Production:
2,3-Dimethylbenzothiophene is used as a chemical intermediate in the production of fuels, contributing to the formulation of various fuel types that power vehicles and industrial machinery.
Used in Lubricant Production:
2,3-DIMETHYLBENZOTHIOPHENE serves as a key ingredient in the manufacturing of lubricants, enhancing the performance and longevity of machinery by reducing friction and wear.
Used in Industrial Product Manufacturing:
2,3-Dimethylbenzothiophene is utilized in the creation of a range of industrial products, where its chemical properties are harnessed to achieve specific performance characteristics.
Environmental Considerations:
Due to its potential toxicity and persistence in the environment, 2,3-Dimethylbenzothiophene is used with caution, and strict handling and disposal protocols are necessary to minimize its impact on human health and the environment.

InChI:InChI=1/C10H10S/c1-7-8(2)11-10-6-4-3-5-9(7)10/h3-6H,1-2H3

Upstream product

• 58863-51-7 2-chloromethyl-3-methylbenzothiophene 
• 70445-88-4 1-oxo-2,3-dimethylbenzothiophene 
• 63996-66-7 2-methyl-2-(phenylthio)propanal 
• 503-17-3 dimethylacetylene 
• 60-29-7 diethyl ether 
• 541-41-3 chloroformic acid ethyl ester 
• 108-98-5 thiophenol 
• 536-74-3 phenylacetylene 
• 6287-82-7 2,3-dibromobenzo[b]thiophene 
• 934-87-2 S-phenyl thioacetate 
• 26074-25-9 3-chloro-3-methyl-pentane-2,4-dione 
• 1455-18-1 3-methylbenzothiophene 
• 74-88-4 methyl iodide 
• 10243-15-9 3-bromo-2-methylbenzo[b]thiophene 

Downstream Products

• 1505-52-8 3-methylbenzo[b]-thiophene-2-acetic acid 
• 1372135-18-6 2-(4-methoxybenzyl)-3-methylbenzo[b]thiophene 

Relevant academic research and scientific papers

Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF

We describe the double-carboxylation of two C-H bonds (i.e., at the benzylic and the β-positions) in 2-alkylheteroarenes using a combination of LiO-t-Bu and CsF. A diverse range of substrates, namely benzothiophene, thiophene, benzofuran, furan, and indole derivatives, are efficiently converted into the doubly carboxylated products. A variety of functionalities (i.e., methyl, methoxy, halogen, cyano, ester, ketone, and amide moieties) are well tolerated.

Integration of a Four-Step Reaction into One-Pot under the Coexistence of Silica-Gel-Supported Acid and Base Reagents: Synthesis of Benzo- and Naphthothiophenes Using NaHSO 4 /SiO 2 and Na 2 CO 3 /SiO 2

A four-step synthesis of benzo- and naphthothiophenes that have biological importance and application in material science was integrated into a one-pot reaction by using silica gel-supported acid and base reagents, NaHSO 4 /SiO 2 and Na 2 CO 3 /SiO 2. The supported reagents provided acid and base environments on the surface of the supports without neutralization and worked separately in the same medium. The four-step reaction comprises (i) deacetylation of 3-halo-2,4-pentanediones to α-halo ketones, (ii) deacetylation of S -aryl thioacetates to arenethiols, (iii) coupling of α-halo ketones and arenethiols to give α-sulfanyl ketones, and (iv) cyclization of sulfanyl ketones to benzo- and naphthothiophenes. The steps (i) and (iii) proceeded by Na 2 CO 3 /SiO 2, and (ii) and (iv) by NaHSO 4 /SiO 2. The four-step reaction proceeded efficiently by introduction of starting materials and reagents in a single reaction vessel. The starting materials were very easy to handle and unpleasant smell of aryl thiols that were used in conventional methods could be avoided. Novel thirty-nine benzo- and naphthothiophenes were synthesized by this method in excellent to fair yields.

Practical synthesis of photochromic diarylethenes in integrated flow microreactor systems

An effective method for the synthesis of photochromic diarylethenes through the generation of heteroaryllithiums and subsequent reaction with octafluorocyclopentene has been developed by using integrated flow microreactor systems. Reactions can be conducted without using cryogenic conditions by virtue of effective temperature and residence time control, although much lower temperatures (-1. Therefore, the present integrated flow microreactor method serves as a practical way of synthesizing various photochromic diarylethene derivatives. Too successful to be cool: An effective method for the synthesis of photochromic diarylethenes has been developed by using integrated flow microreactor systems. Reactions can be conducted without the need for cryogenic conditions by using these systems (see picture). The synthesis of unsymmetrical diarylethenes, which is difficult to achieve by using conventional macro batch systems, has also been accomplished. Copyright

Switching reaction pathways of benzo[b]thiophen-3-yllithium and benzo[b]furan-3-yllithium based on high-resolution residence-time and temperature control in a flow microreactor

Reaction-pathway control of benzo[b]thiophen-3-yllithium and benzo[b]furan-3-yllithium was accomplished in flow microreactor systems. We could switch between the reaction with an electrophile before ring-opening and that after ring-opening at will by choosing an appropriate residence-time and temperature.

Free-Radical Reactions of Benzenethiol and Diphenyl Disulphide with Alkynes. Chemical Reactivity of Intermediate 2-(Phenylthio)vinyl Radicals

Reaction of benzenethiol at 100 deg C with neat alkyl- and dialkyl-acetylenes leads to virtually quantitative formation of isomeric mixtures of (E)- and (Z)-vinyl sulphide adducts in ratios which depend largely upon both the extent and the nature of alkyl substitution.Results are explained in terms of rapidly interconverting sp2-hybridized (E)- and (Z)-1-alkyl-2-(phenylthio)vinyl radical intermediates which can undergo hydrogen transfer from benzenethiol to an extent which is essentially dependent upon the steric hindrance of their cis-2-substituent.Consistent results are provided by related radical reactions of diphenyl disulphide with alkyl-substituted alkynes to afford varying amounts of 1,2-bis(phenylthio)ethylene adducts ascribable to SH2 reaction of the resulting 1-alkyl-2-(phenylthio)vinyl radicals with the disulphide present.Under analogous conditions benzenethiol and diphenyl disulphide react with phenylacetylenes to give vinyl sulphide or bissulphide adducts in a trans-stereoselective fashio.The findings are interpreted by suggesting, for the intermediate sp-hybridized 1-phenyl-2-(phenylthio)vinyl radicals, the occurrence of significant bonding interaction between the unpaired electron and the adjacent sulphur, which would essentially prevent attack of radical scavenger on the side cis to PhS.Evidence is also presented that 1-phenyl-2-(phenylthio)vinyl radicals can exhibit homolytic intramolecular cyclization reactions, leading to benzothiophene products to a comparatively much greater extent than the 1-alkyl-2-substituted analogues; however, 1-tert-butyl-2-(phenylthio)vinyl radical would represent a special case.

Synthesis and Reactions of 2,3,5,6-Tetrahydro-2,5-ethano-3-benzazocin-4(1H)-one and a Thieno-extended Analogue: X-Ray Structure of 3-Methyl-2,3,5,6-tetrahydro-2,5-ethanobenzothienoazocin-4(1H)-one

5,6,7,8,9,10-Hexahydro-6,9-methanobenzocyclo-octen-11-one (3) was prepared through condensation of o-xylene-α,α'-diyl dibromide with N-cyclopentylidenepyrrolidine and converted by Beckmann rearrangement of its oxime (4) into 2,3,5,6-tetrahydro-2,5-ethano-3-benzazocin-4(1H)-one (6). 2,3-Bis(bromomethyl)benzothiophene was converted similarly into a mixture of 1,4,5,6-tetrahydro-2,5-ethanobenzothienoazocin-3(2H)-one (15) and the isomeric lactam (19).Lactam (6) was N-methylated and both the parent lactam (6) and the N-methyl derivative (23) were reducedwith lithium aluminium hydride to the saturated products (24) and (25), respectively.Conversion of lactam (6) into the corresponding thiolactam (26) with phosphorus pentasulphide followed by alkylation of the latter compound gave an N-(29) or S-alkylated derivative, (27) or (28), depending on the reagent and reaction conditions.Similar reactions are reported also for lactams (15) and (19).The 4(1H)-one structures of compounds (15) - (22) are based on an X-ray analysis of 3-methyl-2,3,5,6-tetrahydro-2,5-ethanobenzothienoazocin-4(1H)-one (20).We also report syntheses of 2-azido-5,6,7,8,9,10-hexahydro-6,9-methanobenzocyclo-octen-11-one (33) and 3-nitro(and 1,3-dinitro)-6,7,8,9,10,11-hexahydro-7,10-methanocyclo-octabenzothiophen-12-one, (36) and (37), respectively.

An Efficient One-Pot Method for the Preparation of Polysubstituted Benzothiophenes

A one-pot method for the transformation of an aryl bromide, an internal alkyne, and sulfur dichloride into a polysubstituted benzothiophene, in high yield, is described.The method involves the generation and trapping of a zirconocene complex of a substituted benzyne.

Photoreactivity of 2- and 3-Substituted Benzothiophene 1-Oxides in Solution

The photochemical behavior of various benzothiophene sulfoxides (3-methyl, 3-phenyl, 2-methyl, 2-phenyl, 2,3-dimethyl, 2-chloro, 2-bromo, 3-chloro, 3-bromo) has been studied in benzene as solvent.The bromo and chloro derivatives gave no identifiable products.The 3-methyl and 3-phenyl compounds gave three head to head anti photodimers which differ only by the stereochemistry of the S-O bond.The kinetics of the photodimerization of 3-MeBTO was studied as a function of the concentration of substrate, triplet quencher, and triplet sensitizer.A monomeric excited triplet is the proposed precursor of the hth dimer.The 2-methyl derivative led to a photoreduction giving the corresponding sulfide probably through an excited triplet.The 2-phenyl derivative gave a mixture of the photodimer hth and the corresponding sulfide.The behavior of the sulfoxides in these series is different from that of the corresponding sulfones which lead to a mixture of hth and htt dimers for the 2-substituted compounds and to the hth dimer for the 3-substituted ones.