4923-91-5

Basic information

• Product Name: 2,3-DIMETHYLBENZOTHIOPHENE
• Synonyms: 2,3-DIMETHYLBENZOTHIOPHENE
• CAS NO: 4923-91-5
• Molecular Formula: C₁₀H₁₀S
• Molecular Weight: 162.25
• Mol File: 4923-91-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 268.4°C at 760 mmHg
• Flash Point: 84.5°C
• Appearance: /
• Density: 1.114g/cm³
• Vapor Pressure: 0.0127mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 2,3-DIMETHYLBENZOTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHYLBENZOTHIOPHENE(4923-91-5)
• EPA Substance Registry System: 2,3-DIMETHYLBENZOTHIOPHENE(4923-91-5)

Safety Data

• Hazardous Substances Data: 4923-91-5(Hazardous Substances Data)

Usage

General Description

2,3-Dimethylbenzothiophene is a chemical compound with the molecular formula C10H10S. It is a type of heterocyclic aromatic compound that contains a benzene ring fused to a thiophene ring. This chemical is commonly used in the production of fuels, lubricants, and other industrial products. It is also found in some natural sources such as coal tar and crude oil. 2,3-Dimethylbenzothiophene is known for its strong, unpleasant odor and is considered a potential environmental hazard due to its potential toxicity and persistence in the environment. It is important to handle and dispose of this chemical with caution 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 
• 60-29-7 diethyl ether 
• 541-41-3 chloroformic acid ethyl ester 
• 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 
• 3133-88-8 (3-methylbenzo[b]thiophen-2-yl)methanol 
• 78614-64-9 1-Methoxy-1-(phenylsulfanyl)-2-methylpropan-2-ol 
• 13865-50-4 methoxymethyl phenyl sulfide 
• 536-74-3 phenylacetylene 
• 108-98-5 thiophenol 

Downstream Products

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

Relevant articles and documents

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

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.