33775-94-9

Basic information

• Product Name: 2-IODOTHIOANISOLE
• Synonyms: 2-IODOTHIOANISOLE;1-IODO-2-(METHYLTHIO)BENZENE;2-Iodophenyl methyl sulphide~2-(Methylthio)iodobenzene;2-Iodophenyl methyl sulfide;1-Iodo-2-(methylthio)benzene, 95+%;(2-iodophenyl)(methyl)sulfane;1-(Methylthio)-2-iodobenzene;Methyl[2-iodophenyl] sulfide
• CAS NO: 33775-94-9
• Molecular Formula: C₇H₇IS
• Molecular Weight: 250.1
• EINECS: -0
• Mol File: 33775-94-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 129 °C
• Flash Point: 129-131°C/3mm
• Appearance: /
• Density: 1.787 g/cm³
• Vapor Pressure: 0.0298mmHg at 25°C
• Refractive Index: 1.682
• Storage Temp.: 2-8°C(protect from light)
• Sensitive: Light Sensitive
• BRN: 2516385
• CAS DataBase Reference: 2-IODOTHIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODOTHIOANISOLE(33775-94-9)
• EPA Substance Registry System: 2-IODOTHIOANISOLE(33775-94-9)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• HazardClass: LIGHT SENSITIVE, STENCH
• Hazardous Substances Data: 33775-94-9(Hazardous Substances Data)

Usage

Description

2-Iodothioanisole, also known as 2-iodo-1,3-benzodithiole, is a chemical compound characterized by its molecular formula C7H5IS. It presents as a pale yellow to light brown liquid with a distinctive strong odor. 2-IODOTHIOANISOLE is recognized for its utility in various chemical syntheses and material productions, despite its potential to cause irritation and its classification as hazardous to the aquatic environment.

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Iodothioanisole is utilized as a building block in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its unique chemical properties.
Used in Liquid Crystal Material Production:
2-IODOTHIOANISOLE is employed in the production of liquid crystal materials, which are crucial for the manufacturing of displays and other optical devices, owing to their ability to manipulate light under the influence of an electric field.
Used in Dye Production:
2-Iodothioanisole is also used in the creation of dyes, where its strong odor and color characteristics are harnessed for specific applications in the dye industry.
Safety and Environmental Considerations:
Given its potential to cause irritation to the eyes, skin, and respiratory system, 2-Iodothioanisole requires careful handling and the implementation of proper safety measures to protect workers and the environment. Moreover, its classification as hazardous to the aquatic environment necessitates responsible disposal and management practices to mitigate ecological risks.

InChI:InChI=1/C7H7IS/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3

Upstream product

• 19614-16-5 2-bromo-1-(methylsulfanyl)benzene 
• 624-92-0 Dimethyldisulphide 
• 348-52-7 1-Fluoro-2-iodobenzene 
• 136-95-8 2-amino-benzthiazole 
• 137-07-5 2-amino-benzenethiol 
• 137092-18-3 2-Iodo-benzenediazonium; hydrogen sulfate 
• 137092-22-9 Dithiopivalinsaeure-2-iodphenylester 
• 2987-53-3 2-(Methylthio)aniline 

Downstream Products

• 73671-43-9 2-methylthio-2'-nitrobiphenyl 
• 415680-01-2 5-(2-methylmercaptophenyl)-5-hexenenitrile 
• 415680-02-3 trimethyl{[2-(methylsulfanyl)phenyl]ethynyl}silane 
• 124153-79-3 2-methyl-4-(2-(methylthio)phenyl)but-3-yn-2-ol 
• 868861-78-3 3-(2-methanesulfonyl-phenylethynyl)-phenol 
• 26563-22-4 3-bromo-2-(4-methoxyphenyl)benzo[b]thiophene 
• 7342-82-7 3-Bromothianaphthene 

Relevant articles and documents

Synthesis of [1]Benzothieno[3,2- b][1]benzothiophene Derivatives via Successive Iodocyclization/Photocyclization of Alkynes

A new synthetic method for [1]benzothieno[3,2-b][1]benzothiophene derivatives (BTBTs) was developed. The present method consists of iodocyclization of 1,2-bis(2-methylthiophenyl)ethynes and photolysis of 3-iodo-(2-methylthiophenyl)benzo[b]thiophenes. With 1,2-bis(2-methylthiophenyl)ethynes treated with I2/PhI(OAc)2 in CH2Cl2 at room temperature, selective cyclization at sulfur took place to give 3-iodo-(2-methylthiophenyl)benzo[b]thiophenes in good yields. Irradiation of the iodinated benzo[b]thiophenes with a high-pressure Hg lamp (>290 nm) provided BTBTs in good yields. Furthermore, the present method was applied to the synthesis of bis[1]benzothieno[2,3-d;2′,3′-d′]benzo[1,2-b;4,5-b′]dithiophene (BBTBDT).

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.

Copper-catalysed aromatic-Finkelstein reactions with amine-based ligand systems

A new efficient and low-cost ligand, diethylenetriamine, has been utilised to promote the iodination of 16 different bromo-substrates via the copper catalysed Finkelstein halogen exchange reaction under mild conditions. In contrast to earlier methods, the use of inert atmosphere conditions was not required to obtain high yields and purity. Studies on the speciation of the catalyst in solution indicate rapid disproportionation of copper(i) in the presence of diethylenetriamine to give copper(0) and a bis-ligated copper(ii) complex which is characterised by X-ray diffraction. This copper(ii) complex was also shown to be catalytically active in the halogen exchange reaction. In contrast, no significant disproportionation was observed using dimethylethylenediamine as the ligand, and the solid-state structures of a copper(i) dimeric complex and a 2D polymeric network of copper(i) iodide tetramers are reported. The catalytic activity of diethylenetriamine and dimethylethylenediamine with both copper(i) and copper(ii) salts are compared, and possible mechanistic implications discussed.