35371-03-0

Basic information

• Product Name: 4-IODOTHIOANISOLE
• Synonyms: 4-IODOTHIOANISOLE;4-Iodothiaanisole;(4-iodophenyl)(methyl)sulfane;1-(Methylthio)-4-iodobenzene;1-Iodo-4-(methylthio)benzene;Methyl p-iodophenyl sulfide;Methyl(4-iodophenyl) sulfide;p-Iodothioanisole
• CAS NO: 35371-03-0
• Molecular Formula: C₇H₇IS
• Molecular Weight: 250.1
• Mol File: 35371-03-0.mol

Chemical Properties

• Melting Point: 40 °C
• Boiling Point: 262.622 °C at 760 mmHg
• Flash Point: 112.6 °C
• Appearance: /
• Density: 1.787 g/cm³
• Vapor Pressure: 0.0176mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-IODOTHIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODOTHIOANISOLE(35371-03-0)
• EPA Substance Registry System: 4-IODOTHIOANISOLE(35371-03-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 35371-03-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Iodothioanisole is used as a reagent in organic synthesis for its strong electrophilicity, facilitating the creation of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Iodothioanisole is utilized as an important intermediate. Its role is crucial in the synthesis of drugs, contributing to the development of new medicinal compounds.
Used in Agrochemical Production:
4-Iodothioanisole also serves as an intermediate in the production of agrochemicals, playing a part in the creation of substances that protect and enhance crop yields.
Used in Dye Manufacturing:
4-IODOTHIOANISOLE is used as a building block in the manufacturing of dyes, contributing to the coloration and quality of various products.
Used in Specialty Chemicals Production:
4-Iodothioanisole is employed in the production of specialty chemicals, where its unique properties are harnessed for specific applications in different industries.
Due to the reactivity and strong electrophilic nature of 4-Iodothioanisole, it requires careful handling and storage to ensure safety and prevent accidents or exposure.

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

Upstream product

• 52928-01-5 4-iodothiophenol 
• 104-95-0 (4-bromophenyl)thioanisole 
• 100-68-5 methyl-phenyl-thioether 
• 104-96-1 4-methylsulfanylaniline 
• 624-38-4 para-diiodobenzene 
• 74-88-4 methyl iodide 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 624-92-0 Dimethyldisulphide 
• 540-37-4 p-aminoiodobenzene 
• 5122-99-6 4-iodophenylboronic acid 
• 1514-50-7 4-iodobenzenediazonium tetrafluoroborate 
• 870081-83-7 dimethyl{4-(methylthio)phenyl}sulfonium triflate 
• 352-34-1 4-fluoro-1-iodobenzene 
• 13205-48-6 4-(methylthio)benzoic acid 

Downstream Products

• 21203-94-1 1-iodo-4-(methylsulfinyl)benzene 
• 64984-08-3 1-iodo-4-(methylsulfonyl)benzene 
• 98-61-3 p-Iodobenzenesulfonyl chloride 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 33533-42-5 1-[4-(methylsulfanyl)phenyl]-2-phenylacetylene 
• 134317-21-8 1-methylthio-4-[2-(trimethylsilyl)ethynyl]benzene 
• 939899-89-5 3-(4-(methylthio)phenyl)prop-2-yn-1-ol 
• 64-19-7 acetic acid 
• 52323-93-0 1-methanesulfonyl-4-methylsulfanyl-benzene 
• 547768-63-8 ((CH₃)2CH)2NBHC₆H₄SCH₃ 

Relevant articles and documents

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.

t-BuOK-promoted methylthiolation of aryl fluorides with dimethyldisulfide under transition-metal-free and mild conditions

In the presence of potassium tert-butoxide (t-BuOK), the cross-coupling reaction between aryl fluorides and dimethyldisulfide was developed. A series of aryl methyl sulfides were obtained in moderate to good yields under transition-metal-free and mild conditions.

Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust

Readily available aryldimethylsulfonium triflates react with zinc powder under nickel catalysis via the selective cleavage of the sp2-hybridized carbon-sulfur bond to produce salt-free arylzinc triflates under mild conditions. This zincation displays superb chemoselectivity and thus represents a protocol that is complementary or orthogonal to existing methods. The generated arylzinc reagents show both high reactivity and chemoselectivity in palladium-catalyzed and copper-mediated cross-coupling reactions.

Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water

An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.

Photochromic dithienylethenes characterized by: In situ irradiation NMR-spectroscopy and electrochemically induced responsiveness on gold substrates

Photochromic compounds comprising small molecules and polymers have been shown to be of great interest in the field of stimuli-responsive materials for applications as sensors and (nano-) devices. In this regard dithienylethenes (DTEs) have been proven to be especially valuable because of their tolerance to chemicals and their good stability making them tunable and reversibly switchable between an open and a closed structure featuring different optical properties. By utilizing a potent in situ irradiation NMR spectroscopy approach, it is possible to determine the photochromic switching capability of two DTE derivatives in solution leading to crucial information about the structures, the equilibria of the chemical ring-opening and closing of the DTEs as well as the longtime stability of these molecular switches. In particular the perfluorinated thioether bearing compound shows remarkable stability with little fatigue related to the irreversibly cyclized byproduct known for DTEs. The thioether-bearing DTEs can be deprotected and used for immobilization on gold substrates which are characterized by water contact angle measurements prior to and after DTE functionalization. Finally, the electrochemically induced switching capability of the perhydro DTE is investigated by cyclic voltammetry proving its fast, quantitative and reversible cyclization. We envisage these materials for applications as sensors and optical switching devices.

Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen: Development of a base-catalyzed iododeboronation for radiolabeling applications

An investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: General Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation that is amenable to the preparation of 125I-labeled products for SPECT applications.

Visible light-promoted formation of C-B and C-S bonds under metal- A nd photocatalyst-free conditions

A green, efficient, photoinduced synthesis of arylboronic esters and aryl sulfides has been developed. Bench stable arylazo sulfones were used as radical precursors for a photocatalyst- A nd additive-free carbon-heteroatom bond formation under visible light. The protocols are applicable to a wide range of substrates, providing products in good yields.

Metal-Free, DTBP-Mediated Methylthiolation of Arylboronic Acids with Dimethyldisulfide

An efficient method for the C-S bond formation via the coupling reaction of arylboronic acids with dimethyldisulfide has been developed under the metal-free conditions. This novel protocol provides an attractive route for the synthesis of aryl methyl sulf

Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.

Practical and efficient ipso-iodination of arylboronic acids via KF/I2 system

A facile and effective iododeboronation of variously substituted aryl and heteroarylboronic acids through activation and subsequent ipso-introduction of iodine is presented. The use of KF and I2 at 80 °C in 1,4-dioxane furnishes iodinated compounds in high yields.