19614-16-5

Basic information

• Product Name: 2-Bromothioanisole
• Synonyms: 2-BROMOTHIOANISOLE;2-BROMOPHENYL METHYL SULFIDE;1-BROMO-2-(METHYLTHIO)BENZENE;O-BROMOTHIOANISOLE;TIMTEC-BB SBB006566;1-Bromo-2-(methylsulfanyl)benzene;o-Bromo(methylthio)benzene;o-Bromophenyl methyl sulfide
• CAS NO: 19614-16-5
• Molecular Formula: C₇H₇BrS
• Molecular Weight: 203.1
• EINECS: 243-183-4
• Product Categories: Miscellaneous;Thioderivates
• Mol File: 19614-16-5.mol

Chemical Properties

• Melting Point: -24 °C
• Boiling Point: 145-146 °C (27 mmHg)
• Flash Point: >110°C
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.522 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0217mmHg at 25°C
• Refractive Index: 1.632-1.634
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 2243716
• CAS DataBase Reference: 2-Bromothioanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromothioanisole(19614-16-5)
• EPA Substance Registry System: 2-Bromothioanisole(19614-16-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• RIDADR: UN 3334
• WGK Germany: 3
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 19614-16-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Bromothioanisole is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to be a valuable building block in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
2-Bromothioanisole is used as a key component in the development of new pharmaceuticals. Its reactivity and structural properties make it suitable for the creation of novel drug candidates with potential therapeutic applications.
Used in Material Science:
In the field of material science, 2-Bromothioanisole is utilized as a precursor for the synthesis of advanced materials with specific properties. These materials can be used in various applications, such as electronics, coatings, and adhesives.
Used in Research and Development:
2-Bromothioanisole is also employed in research and development laboratories for studying its chemical behavior and exploring its potential applications in various fields. Its unique properties make it an interesting subject for scientific investigation.

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

Upstream product

• 4856-13-7 cuprous methylmercaptide 
• 583-53-9 2,3-dibromobenzene 
• 1072-85-1 o-fluorobromobenzene 
• 40920-16-9 methyl dithiopivalate 
• 2568-36-7 6,6-dibromobicylo[3.1.0]hexane 
• 5188-07-8 sodium thiomethoxide 
• 4973-66-4 methyl thiotosylate 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 126218-83-5 1-bromo-2-(methylsulfinyl)benzene 
• 75-18-3 dimethylsulfide 
• 583-55-1 1-Bromo-2-iodobenzene 
• 624-92-0 Dimethyldisulphide 
• 124-38-9 carbon dioxide 
• 6320-02-1 o-bromothiophenol 

Downstream Products

• 166831-65-8 2,2,2-trifluoro-1-(2-methylsulfanylphenyl)ethanone 
• 24845-02-1 2-methylsulphanylbenzhydrol 
• 1620-95-7 [2-(methylthio)phenyl](phenyl)methanone 
• 32250-83-2 1-(2-Methylsulfanyl-phenyl)-1-phenyl-ethanol 
• 33951-33-6 1-bromo-2-(methylsulfonyl)benzene 
• 7321-58-6 (S)-methyl o-bromophenyl sulfoxide 
• 7321-58-6 (R)-2-bromophenyl methyl sulfoxide 
• 14092-00-3 methyl o-tolyl sulfide 
• 1441-97-0 2'-(methylthio)acetophenone 
• 796854-13-2 ethyl 2-cyano-3-[2-(methylthio)phenyl]-3-(1-naphthyl)propanoate 
• 137207-82-0 5,7-Dimethyl-1-(2-methylsulfanyl-phenyl)-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester 
• 161609-93-4 1-benzyloxycarbonyl-4-hydroxy-4-(2-methylthiophenyl)piperidine 
• 1262546-94-0 1-dimesitylboryl-2-methylthio-benzene 
• 2976-66-1 1-isopropyl-2-methylsulfanyl-benzene 

Relevant articles and documents

SUBSTITUTED 3,4,12,12A-TETRAHYDRO-1H-[1,4]OXAZINO[3,4-C]PYRIDO[2,1-F][1,2,4]TRIAZINE-6,8-DIONE, PHARMACEUTICAL COMPOSITION, AND METHODS FOR PREPARING AND USING SAME

Influenza is an acute infectious respiratory disease caused by the influenza virus. It is part of the group of Acute Respiratory Viral Infections (ARVI). It occasionally spreads in the form of epidemics and pandemics. Currently, more than 2000 variants of the influenza virus differing in the antigen spectrum have been identified. Given that influenza is a serious threat to public health (worldwide, these annual epidemics lead to 3-5 million cases of severe illness, millions of hospitalizations, and up to 650,000 deaths), it seems appropriate to search for new anti-influenza drugs with improved characteristics. The inventors surprisingly found out that the previously unknown substituted 3,4,12,12a-tetrahydro-1 H-[1,4] oxazino[3,4-c]pyrido[2,1-f] [1,2,4]triazine-6,8-dione of general formula 1, its stereoisomer, their prodrug, pharmaceutically acceptable salt, solvate, hydrate, and a crystalline or polycrystalline form thereof are effective agents for prophylaxis and treatment of viral diseases, including influenza where R1 is (6,7-difluoro-5,10-dihydrothieno[3,2-c][2]benzothiepin-10-yl, (7,8-difluoro-4,9-dihydrothieno[2,23-c][2]benzothiepin-4-yl, (3,4-difluorophenyl)(phenyl)methyl, (3,4-difluorophenyl)(2-methylsulfanylphenyl)methyl, diphenylmethyl, bis(4-fluorophenyl)-methyl; R2 is hydrogen or a protective group selected from a series comprising (C1-C3 alkyl) oxycarbonyloxy, {[(C1-C3 alkyl)oxycarbonyl]-oxy}methoxy, {[2-(C1-C3 alkyl) oxyethoxy]carbonyl}oxy, ({[(1R)-2-[(C1-C3alkyl)oxy]-1-methylethoxy}carbonyl)oxy, {[(3S)-ethoxyfuran-3-yloxy]-carbonyl}oxy, [(ethoxy-2H-pyran-4-yloxy)carbonyl]oxy,{[(1-acetylazetidine)-3-yloxy]carbonyl}oxy, {[(C1-C3alkyl) oxycarbonyl] -oxy}methoxy, ({[2-(C1-C3 alkyl)oxyethoxy]carbonyl}oxy) methoxy.

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst

We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.

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.

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.

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.

A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

The general catalytic synthesis of aryl and vinyl thioethers from readily available halides remains a challenge. Herein we report a unified method for the thiolation of aryl and vinyl iodides with dialkyl disulfides using visible light photoredox catalysis. A range of thioether products bearing diverse functional groups can be accessed in high yield and with excellent chemoselectivity. We demonstrate the versatility of this method through the expedient synthesis of a family of thioether-rich natural products. A detailed investigation of the photocatalytic mechanism is presented from both steady-state and time-resolved luminescent quenching as well as transient absorption spectroscopy experiments.

Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics

Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.

METHOD FOR PRODUCING SULFIDE

PROBLEM TO BE SOLVED: To provide a method that performs a deoxygenation reaction of a sulfoxide using hydrogen as a reductant, and produces a corresponding sulfide. SOLUTION: A method for producing a sulfide is characterized by performing a deoxygenation reaction of a sulfoxide in the presence of a platinum-carrying molybdenum trioxide catalyst in which a platinum particle is immobilized to a molybdenum trioxide, and hydrogen, to obtain a corresponding sulfide. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Mild Deoxygenation of Sulfoxides over Plasmonic Molybdenum Oxide Hybrid with Dramatic Activity Enhancement under Visible Light

Harvesting solar light to boost commercially important organic synthesis still remains a challenge. Coupling of conventional noble metal catalysts with plasmonic oxide materials which exhibit intense plasmon absorption in the visible light region is a promising option for efficient solar energy utilization in catalysis. Herein, we for the first time demonstrate that plasmonic hydrogen molybdenum bronze coupled with Pt nanoparticles (Pt/HxMoO3-y) shows a high catalytic performance in the deoxygenation of sulfoxides with 1 atm of H2 at room temperature, with dramatic activity enhancement under visible light irradiation relative to dark conditions. The plasmonic molybdenum oxide hybrids with strong plasmon resonance peaks pinning at around 556 nm are obtained via a facile H-spillover process. Pt/HxMoO3-y hybrid provides excellent selectivity for the deoxygenation of various sulfoxides as well as pyridine N-oxides, in which drastically improved catalytic efficiencies are obtained under the irradiation of visible light. Comprehensive analyses reveal that oxygen vacancies massively introduced via a H-spillover process are the main active sites, and the reversible redox property of Mo atoms and strong plasmonic absorption play key roles in this reaction. The catalytic system works under extremely mild conditions and can boost the reaction by the assistance of visible light, offering an ultimately greener protocol to produce sulfides from sulfoxides. Our findings may open up a new strategy for designing plasmon-based catalytic systems that can harness visible light efficiently.

METHOD FOR PRODUCING PHENOTHIAZINE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method for producing a phenothiazine derivative that has reduced limitations on the number of functional groups that can be arranged to it, prevents the occurrence of by-products, and secures high yields. SOLUTION: A method for producing a phenothiazine derivative includes the step of reacting a benzyne precursor with a compound represented by formula (A) (RA1-RA5 independently represent H, a hydroxy group or an organic group, RA1 and RA2, RA2 and RA3, RA3 and RA4 may together form, with an adjacent atom, a 5-8 membered ring; RA6 is H or an optionally substituted C1-C20 hydrocarbon group; X is a halogen atom). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT