104-95-0

Basic information

• Product Name: 4-Bromothioanisole
• Synonyms: 1-BROMO-4-(METHYLTHIO)BENZENE;4-BROMOTHIOANISOLE 98%;(4-bromophenyl)(methyl)sulfane;4-(Methylthio)-1-bromobenzene;4-Bromothioanisole,97%;1-Bromo-4-(methylsulphanyl)benzene, 1-Bromo-4-(methylthio)benzene;4-BroMothioanisole, 97% 5GR;1-Bromo-4-(methylthio)benzene 4-Bromophenyl Methyl Sulfide
• CAS NO: 104-95-0
• Molecular Formula: C₇H₇BrS
• Molecular Weight: 203.1
• EINECS: 203-255-8
• Product Categories: Miscellaneous;Thioderivates;blocks;Bromides
• Mol File: 104-95-0.mol
• Article Data: 81

Chemical Properties

• Melting Point: 38-40 °C(lit.)
• Boiling Point: 128-130 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to beige/Low Melting Crystalline Mass, Crystals, Crystalline Powder or Chunks
• Density: 1.5027 (estimate)
• Vapor Pressure: 0.0537mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 0-10°C
• Sensitive: Stench
• BRN: 1906693
• CAS DataBase Reference: 4-Bromothioanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromothioanisole(104-95-0)
• EPA Substance Registry System: 4-Bromothioanisole(104-95-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• RIDADR: UN 3335
• WGK Germany: 3
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 104-95-0(Hazardous Substances Data)

Usage

Description

4-Bromothioanisole is an organic compound characterized by its white to beige low melting crystalline mass. It is known for undergoing Heck olefination reaction with styrenes to yield stilbenes, which is a significant chemical property.

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

• 100-68-5 methyl-phenyl-thioether 
• 3406-76-6 (4-bromophenylthio)acetic acid 
• 616-38-6 carbonic acid dimethyl ester 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 624-92-0 Dimethyldisulphide 
• 106-37-6 1.4-dibromobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 5188-07-8 sodium thiomethoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 934-71-4 1-bromo-4-(methylsulfinyl)benzene 
• 124-38-9 carbon dioxide 
• 106-53-6 para-bromobenzenethiol 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 56075-37-7 1-(methylsulfonyl)-2-(4-bromophenyl)diazene 

Downstream Products

• 73242-19-0 2,2-dimethyl-1-(4-(methylthio)phenyl)propan-1-one 
• 100-25-4 para-dinitrobenzene 
• 3466-32-8 4-bromoohenyl methyl sulfone 
• 345635-35-0 (2,4-dibromo-phenyl)-methyl sulfide 
• 28227-62-5 (R)-1-bromo-4-(methylsulfinyl)benzene 
• 22515-25-9 [4-(methylsulfanyl)phenyl]trimethylsilane 
• 125872-45-9 ethyl (E)-3-<4-(methylthio)phenyl>propenoate 
• 477885-33-9 3-(4-methylsulfanyl-phenyl)-propionic acid ethyl ester 
• 21134-14-5 methyl (4-phenyloxy)phenyl sulfide 
• 844856-40-2 3'-bromo-4-methylthiobiphenyl 
• 190966-43-9 2-bromo-3-(4-(methylthio)phenyl)-2-cyclopenten-1-one 
• 33932-80-8 4-(methylthio)phenyl phenyl sulfide 
• 203631-79-2 C₂₂H₂₂OS₃ 
• 203631-77-0 C₁₆H₁₈OS₂ 

Relevant articles and documents

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.

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.

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

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.

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.

Nickel phosphide nanoalloy catalyst for the selective deoxygenation of sulfoxides to sulfides under ambient H2pressure

Exploring novel catalysis by less common, metal-non-metal nanoalloys is of great interest in organic synthesis. We herein report a titanium-dioxide-supported nickel phosphide nanoalloy (nano-Ni2P/TiO2) that exhibits high catalytic activity for the deoxygenation of sulfoxides. nano-Ni2P/TiO2 deoxygenated various sulfoxides to sulfides under 1 bar of H2, representing the first non-noble metal catalyst for sulfoxide deoxygenation under ambient H2 pressure. Spectroscopic analyses revealed that this high activity is due to cooperative catalysis by nano-Ni2P and TiO2. This journal is

Photochemical Sandmeyer-type Halogenation of Arenediazonium Salts

Trihalide salts were found to efficiently promote photochemical dediazotizing halogenations of diazonium salts. In contrast to classical Sandmeyer reactions, no metal catalysts are required to achieve high yields and outstanding selectivities for halogena

Synthesis of Aryl Methyl Sulfides from Arysulfonyl Chlorides with Dimethyl Carbonate as the Solvent and C1 Source

A new procedure for the synthesis of aryl methyl sulfides from dimethyl carbonate (DMC) and arylsulfonyl chlorides has been achieved. In this strategy, DMC plays a dual role as both, C1 building block and green solvent. Arylsulfonyl chlorides served as the sulfur precursors, and a variety of aryl methyl sulfides were obtained in moderate to excellent yields with good functional group tolerance. Additionally, alkylsulfonyl chloride and dibenzyl carbonate are proven to be suitable substrates as well.

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.