104-95-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromothioanisole is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. It plays a crucial role in the production of specific organic molecules that have potential applications in the development of drugs.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-Bromothioanisole is utilized as a reagent in the synthesis of several organic compounds, such as 4′-nitro-4-mercaptobiphenyl, 4′-iodo-4-mercaptobiphenyl, 3′-nitro-4-mercaptobiphenyl, 3′-iodo-4-mercaptiobiphenyl, and (S)-(–)-p-bromophenyl methyl sulfoxide. These synthesized compounds can have various applications in different industries.
Used in Toxicology Research:
4-Bromothioanisole is also used as a urinary metabolite of bromobenzene in rats, which makes it valuable in toxicology research. Studying its metabolism can provide insights into the effects of bromobenzene and related compounds on biological systems.
Overall, 4-Bromothioanisole is a versatile compound with applications in the pharmaceutical industry, chemical synthesis, and toxicology research, making it an important component in the development of new drugs and understanding the impact of certain chemicals on living organisms.

InChI:InChI=1/C7H7BrS/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 100-68-5 methyl-phenyl-thioether 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 106-53-6 para-bromobenzenethiol 
• 77-78-1 dimethyl sulfate 
• 3406-76-6 (4-bromophenylthio)acetic acid 
• 82244-58-4 1-bromo-4-<²H3>methylthiobenzene 
• 161573-70-2 <(4-bromophenylsulfinyl)(metoxycarbonyl)methylene>triphenylphosphorane 
• 74-88-4 methyl iodide 
• 75-15-0 carbon disulfide 
• 7726-95-6 bromine 
• 5188-07-8 sodium thiomethoxide 
• 934-71-4 1-bromo-4-(methylsulfinyl)benzene 

Downstream Products

• 13205-48-6 4-(methylthio)benzoic acid 
• 100-68-5 methyl-phenyl-thioether 
• 623-13-2 4-methylphenyl methylsulfide 
• 934-71-4 1-bromo-4-(methylsulfinyl)benzene 
• 27691-35-6 1-bromo-4-[(chloromethyl)sulfanyl]benzene 
• 3466-32-8 4-bromoohenyl methyl sulfone 
• 345635-35-0 (2,4-dibromo-phenyl)-methyl sulfide 
• 179748-73-3 (4-bromophenyl)(trichloromethyl)sulfane 
• 35958-19-1 N-(4-methylsulfanyl-phenyl)-anthranilic acid 
• 22515-25-9 [4-(methylsulfanyl)phenyl]trimethylsilane 
• 53104-01-1 N-tert-Butyl-N-(4-methylsulfanyl-phenyl)-hydroxylamine 
• 92191-50-9 7-(4-Methylmercapto-phenyl)-tropiliden 
• 51953-89-0 (E)-3-(4-Methylsulfanyl-phenyl)-acrylic acid methyl ester 
• 1591-30-6 (1,1'-biphenyl)-4,4'-dicarbonitrile 

Relevant academic research and scientific papers

A mild protocol for the deoxygenation of α-hydrogen-containing sulfoxides to the corresponding sulfides

A mild method for the deoxygenation of α-hydrogen-containing sulfoxides to sulfides is reported. This synthetically useful and operationally simple protocol derives mechanistically from the Swern oxidation methodology.

Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides

We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.

Scalable electrochemical reduction of sulfoxides to sulfides

A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.

Chemoenzymatic Deracemization of Chiral Sulfoxides

The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine-type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides.

Highly efficient deoxygenation of sulfoxides using hydroxyapatite-supported ruthenium nanoparticles

We report the first example of the deoxygenation of sulfoxides using heterogeneous catalysts with alcohols as environmentally friendly reducing reagents. Hydroxyapatitesupported Ru nanoparticles (RuNPs/HAP) act as a highly efficient and reusable heterogeneous catalyst for deoxygenation of sulfoxides using alcohols as reductants. The catalytic activity of Ru nanoparticles is outstanding compared to other metal nanoparticles such as Pt, Pd, Rh, and Au nanoparticles. RuNPs/HAP can also catalyze the selective deoxygenation of various sulfoxides, giving the corresponding sulfides in excellent yields.

In situ acidic carbon dioxide/ethanol system for selective oxybromination of aromatic ethers catalyzed by copper chloride

An environmentally benign carbon dioxide/ethanol reversible acidic system was developed for the copper(II)-catalyzed regioselective oxybromination of aromatic ethers without the need of any conventional acid additive and organic solvent. Good to excellent yields together with very good regioselectivity were achieved when easily available cupric chloride dihydrate was used as catalyst and lithium bromide as the cheap and easy-to-handle bromine source under supercritical carbon dioxide conditions. Notably, the catalytic system worked well for a wide range of aromatic ethers including sulfides, resulting in the formation of the mono-brominated products in high yields and exclusive regioselectivity. The alkylcarbonic acid in situ formed from ethanol and carbon dioxide is assumed to play the crucial role in the Braonsted acid-promoted reaction, which could probably act as the proton donator, and was studied employing in situ FT-IR technique under carbon dioxide pressure by monitoring the vibration shift of the hydroxy group of ethanol. Given with excellent bromine atom efficiency as well as no need of neutralization in waste disposal, this approach thus represents a greener pathway for the aerobic bromination of aromatic ethers. A possible catalytic cycle for the in situ alkylcarbonic acid-assisted oxybomination and the effect of supercritical carbon dioxide, i.e., activation of alcohol and enhancement of mass transfer are also discussed. Copyright

Linker Deficiency, Aromatic Ring Fusion, and Electrocatalysis in a Porous Ni8-Pyrazolate Network

The cruciform linker molecule here features two designer functions: the pyrazole donors for framework construction, and the vicinal alkynyl units for benzannulation to form nanographene units into the Ni8-pyrazolate scaffold. Unlike the full 12 connections of the Ni8(OH)4(H2O)2 clusters in other Ni8-pyrazolate networks, significant linker deficiency was observed here, leaving about half of the Ni(II) sites capped by acetate ligands, which can be potentially removed to open the metal sites for reactivity. The crystalline Ni8-pyrazolate scaffold also retains the crystalline order even after thermal treatments (up to 300 °C) that served to partially graphitize the neighboring alkyne units. The resultant nanographene components enhance the electroactive properties of the porous hosts, achieving hydrogen evolution reaction (HER) activity that rivals that of topical nickel/palladium-enabled materials.

A practical and chemoselective Mo-catalysed sulfoxide reduction protocol using a 3-mercaptopropyl-functionalized silica gel (MPS)

A convenient sulfoxide deoxygenation procedure using a mercaptopropyl-functionalized silica gel as the reducing agent is described. This new protocol based on a heterogeneous reagent displays broad scope and tolerance to reducible functional groups and, from an experimental point of view, enhances previous methods by simplifying the isolation of the sulfide to a simple filtration.

Homolytic Cleavage of a B-B Bond by the Cooperative Catalysis of Two Lewis Bases: Computational Design and Experimental Verification

Density functional theory (DFT) investigations revealed that 4-cyanopyridine was capable of homolytically cleaving the B-B σ bond of diborane via the cooperative coordination to the two boron atoms of the diborane to generate pyridine boryl radicals. Our experimental verification provides supportive evidence for this new B-B activation mode. With this novel activation strategy, we have experimentally realized the catalytic reduction of azo-compounds to hydrazine derivatives, deoxygenation of sulfoxides to sulfides, and reduction of quinones with B2(pin)2 at mild conditions. Breaking good: The diborane B-B bond can be homolytically cleaved via the cooperative catalysis of two 4-cyanopyridine molecules. Using this combination of a diborane (B2(pin)2) and 4-cyanopyridine also allows the catalytic reduction of the N=N double bond of azo-compounds to hydrazine derivatives, deoxygenation of sulfoxides to sulfides, and reduction of quinones under mild conditions.

Efficient hydrodeoxygenation of sulfoxides into sulfides under mild conditions using heterogeneous cobalt-molybdenum catalysts

Nitrogen-doped carbon-supported cobalt-molybdenum bimetallic catalysts (abbreviated as Co-Mo/NC) are active for the hydrodeoxygenation of sulfoxides to sulfides under mild conditions (25-80 °C and 10 bar H2), which represents the first example of the use of heterogeneous non-noble metal catalysts for this transformation. MoO3 with Lewis acid sites assists the hydrodeoxygenation of sulfoxides into sulfides by hydrogen over cobalt nanoparticles.