37972-89-7

Basic information

• Product Name: 2-iodothiophenol
• Synonyms: 2-iodothiophenol
• CAS NO: 37972-89-7
• Molecular Formula: C₆H₅IS
• Molecular Weight: 236.07337
• EINECS: -0
• Mol File: 37972-89-7.mol

Chemical Properties

• Boiling Point: 119.5 °C(Press: 11 Torr)
• Appearance: /
• Density: 1.901±0.06 g/cm3(Predicted)
• PKA: 5.96±0.43(Predicted)
• CAS DataBase Reference: 2-iodothiophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-iodothiophenol(37972-89-7)
• EPA Substance Registry System: 2-iodothiophenol(37972-89-7)

Safety Data

• Hazardous Substances Data: 37972-89-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Iodothiophenol is used as a building block in organic synthesis for the formation of heterocyclic compounds, which are important in various chemical and pharmaceutical applications.
Used in Pharmaceutical Preparation:
It serves as a key intermediate in the preparation of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
2-Iodothiophenol is utilized in the synthesis of agrochemicals, playing a role in the creation of pesticides and other agricultural chemicals to protect crops and enhance yields.
Used in Dye Manufacturing:
2-iodothiophenol is also employed in the production of dyes, where its unique properties contribute to the color and stability of various dye products.
In all applications, due to the reactivity and potential toxicity of 2-iodothiophenol, it is crucial to implement proper safety measures during its use to ensure the well-being of workers and the environment.

Upstream product

• 98554-55-3 (2-Iodo-phenylsulfanyl)-acetic acid 
• 615-43-0 2-iodophenylamine 
• 56410-50-5 2-iodo benzene diazonium chloride 
• 69646-18-0 (2-iodophenyl)ethylxanthate 

Downstream Products

• 154180-33-3 2-cyclohexenyl 2-iodophenyl sulfide 
• 73033-74-6 1α-(2-iodophenylthio)-17β-acetoxy-5α-androstan-3-one 
• 19374-74-4 6-phenyl-6H-dibenzo[c,e][1,2]thiaborinine 
• 1337956-21-4 2-(12H-11,12-diazaindeno[2,1-a]fluoren-11-yl)benzenethiol 
• 27943-36-8 3,3-dimethylthiochroman-4-one 
• 1034921-53-3 3,3-dimethyl-3,4-dihydro-2H-1-benzothiopyran-4-ol 

Relevant articles and documents

Palladium-catalyzed domino ring-opening/carboxamidation reactions of N -tosyl aziridines and 2-iodothiophenols: A facile and efficient approach to 1,4-benzothiazepin-5-ones

A novel and efficient domino procedure has been developed for the synthesis of 1,4-benzothiazepin-5-ones from simple and readily accessible N-tosyl aziridines and o-iodothiophenols. This process involves aziridines ring-opening with o-iodothiophenols, followed by palladium-catalyzed intramolecular carboxamidation. The scope and limitation of this transformation have been investigated in detail by using various aziridines and o-iodothiophenols.

Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis

Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acid medium. The product of oxidation is the corresponding thiophenol. The rate data of meta- and para-substituted acids have been correlated well with σI, σ°R values and the meta-compounds correlate well with F,R values. The reaction constants are negative and of smaller magnitudes. Further, the ortho-substituted acids show a good correlation with triparametric equation involving Taft's σI and σ°R and charton's steric parameter v. There is no considerable steric contribution to the total orthosubstituent effect. Based on these observations, the mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.

Regioselective Carbonylative Heteroannulation of o-Iodothiophenols with Allenes and Carbon Monoxide Catalyzed by a Palladium Complex: A Novel and Efficient Access to Thiochroman-4-one Derivatives

The palladium-catalyzed carbonylative ring-forming reactions of 2-iodothiophenol, and the corresponding substituted derivatives, with allenes and carbon monoxide are described. The reactions afford thiochroman-4-ones in good to excellent isolated yields with quite high regioselectivity. The catalytic heteroannulation may involve regioselective addition of the sulfur moiety of the reactants on the more positive end of the allene, arylpalladium formation, CO insertion, subsequent intramolecular cyclization, and then reductive elimination. The regioselectivity is probably governed by electronic effects.

Oxidative Cleavage of S-Arylmercaptoacetic Acids by Sodium Perborate: Kinetic and Correlation Study

Kinetics of oxidation of twenty six S-arylmercaptoacetic acids (SAMA) (I) by sodium perborate (PB) have been studied in acid medium.The product of oxidation is the corresponding thiophenol.The rate data of meta- and para-substituted acids have been correlated with DSP equations.While the para-compounds correlate well with ?I and ?0R values, the meta-compounds correlate well with ?I and ?-R values.The reaction constants are negative and of smaller magnitudes.Further, the ortho-substituted acids show a good correlation with a triparametric equation involving Taft's ?I and ?0R and Charton's steric parameter ν.There is a considerable steric contribution to the total ortho-substituent effect.Based on these observations, mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.

Preparation of Benzothiophenes by Pd(0)-Catalyzed Intramolecular Cyclization of Allyl (and Propargyl) o-Iodophenyl Sulfides

Benzothiophenes are prepared by intramolecular Pd(0)-catalyzed Heck reaction of allyl o-iodophenyl sulfides.Pd(0)-Catalyzed intramolecular cyclization of o-iodophenyl propargyl sulfide in the presence of a hydride donor gives 3-methylene-2,3-dihydrobenzothiophene, which reacts with several enophiles in ene type reactions.However, allyl (and propargyl) aryl sulfides react with palladium(II) chloride to afford polymeric 2.