6320-02-1

Basic information

• Product Name: 2-BROMOTHIOPHENOL
• Synonyms: 2-BROMOBENZENETHIOL;2-BROMOTHIOPHENOL;O-BROMOBENZENETHIOL;2-bromo-benzenethio;Benzenethiol, 2-bromo-;Benzenethiol, o-bromo-;o-Bromothiophenol;2-Bromophenyl mercaptan
• CAS NO: 6320-02-1
• Molecular Formula: C₆H₅BrS
• Molecular Weight: 189.07
• EINECS: 228-665-4
• Product Categories: Phenol&Thiophenol&Mercaptan
• Mol File: 6320-02-1.mol

Chemical Properties

• Melting Point: 220-222 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 128-130 °C25 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colorless to very deep yellow/Liquid
• Density: 1.573 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0568mmHg at 25°C
• Refractive Index: n20/D 1.635(lit.)
• Storage Temp.: −20°C
• PKA: 5.90±0.43(Predicted)
• Sensitive: Stench
• BRN: 2039769
• CAS DataBase Reference: 2-BROMOTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOTHIOPHENOL(6320-02-1)
• EPA Substance Registry System: 2-BROMOTHIOPHENOL(6320-02-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-7/9
• RIDADR: UN2922
• WGK Germany: 3
• F: 10-13-23
• TSCA: T
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6320-02-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Bromothiophenol is used as a chemical intermediate for the synthesis of various organic compounds. Its reactivity with other molecules makes it a valuable building block in the creation of new chemical entities.
Used in Pharmaceutical Industry:
2-Bromothiophenol is used as a starting material for the development of pharmaceutical compounds. Its unique structure and reactivity can be exploited to design and synthesize new drugs with potential therapeutic applications.
Used in Material Science:
2-Bromothiophenol can be utilized in the development of novel materials, such as polymers and coatings, due to its chemical properties. Its ability to form nitro-sulphide compounds can be particularly useful in creating materials with specific properties for various applications.
Used in Research and Development:
2-Bromothiophenol serves as a valuable compound for research purposes, particularly in the fields of organic chemistry and materials science. It can be used to study reaction mechanisms, explore new synthetic routes, and develop innovative applications in various industries.

InChI:InChI=1/C6H5BrS/c7-5-3-1-2-4-6(5)8/h1-4,8H/p-1

Upstream product

• 17333-81-2 o-bromobenzenediazonium 
• 140-89-6 potassium ethyl xanthogenate 
• 615-36-1 2-bromoaniline 
• 15939-85-2 2-((2-bromophenyl)thio)acetic acid 
• 108-98-5 thiophenol 
• 34835-57-9 2-bromo benzene diazonium chloride 
• 583-55-1 1-Bromo-2-iodobenzene 
• 39128-19-3 (2-bromophenyl)ethylxanthate 

Downstream Products

• 71112-91-9 bis(2-bromophenyl) disulfide 
• 103052-99-9 S-(2-bromophenyl) ethanethioate 
• 19614-16-5 2-bromo-1-(methylsulfanyl)benzene 
• 100125-58-4 2-bromophenyl 4-chloro-2-nitrophenyl sulfide 
• 18587-39-8 5-(2-bromo-phenylsulfanyl)-4-nitro-isothiazole 
• 30483-77-3 4-[4-(2-bromo-phenylsulfanyl)-3-nitro-phenyl]-morpholine 
• 18587-37-6 5-(2-bromo-phenylsulfanyl)-3-methyl-4-nitro-isothiazole 
• 16771-05-4 2'-Brom-,4-chlor-2,6-dinitro-diphenylsulfid 
• 7623-76-9 2-(2-bromophenolthio)-5-(methylthio)nitrobenzene 
• 17801-96-6 2'-Brom-4-chlor-5-isopropyloxy-2-nitro-diphenylsulfid 
• 17801-91-1 2'-Brom-4-chlor-5-benzyloxy-2-nitro-diphenylsulfid 
• 17844-93-8 2'-Brom-4-chlor-5-hydroxy-2-nitro-diphenylsulfid 
• 16762-87-1 2'-Brom-4-chlor-2-nitro-3-isopropyloxy-diphenylsulfid 
• 17844-52-9 2'-Brom-4-chlor-5-methoxy-2-nitro-diphenylsulfid 

Relevant articles and documents

SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF

The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017

Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol

A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.

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.

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.

Peroxide Salts as Reagents in Oxidative Halogenation of Aromatic Compounds

Chloromesitylene, chloro-p-xylene, and 1-bromonaphthalene are formed in 78, 79, and 86percent yield, respectively, under the action of the halogenating system hydrogen peroxide-hydrohalic acid-AcOH.The following aryl halides are also formed in high yields in this halogenating system: 2-bromothiophene (89 - 92percent) upon bromonation of thiophene; chlorobenzene (77 - 79percent) and iodobenzene (79 - 81percent) upon chlorination and iodination of benzene.

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.

Electrophilic Aromatic Substitution. Part 33. Partial Rate Factors for Protiodetritiation of Benzothiophen; the Resonance-dependent Reactivity of the Ring Positions

Rate coefficients for detriation of benzothiophen, specifically labelled with tritium at each position, have been measured in anhydrous trifluoroacetic acid, and, for benzothiophen, in a range of trifluoroacetic acid-acetic acid mixtures, all at 70 deg C.The dependence of rate upon acidity is consistent with the effect of hydrogen bonding between sulphur and trifluoroacetic acid, as found previously for other sulphur-containing heterocycles.Partial rate factors, corrected for the effect of hydrogen bonding are (positions in parentheses): 8.84 * 105 (2); 1.18 * 106 (3); 360 (4); 13200 (5); 16200 (6); and 26.2 (7); the corresponding ?+ values are -0.68, -0.695, -0.29, -0.47, -0.48, and -0.16.The positional reactivity order is the same as found in pyrolysis of 1-arylethyl acetates, and solvolysis of 1-arylethyl chlorides, but the ?+ values are more negative due to the greater demand for resonance stabilization of the transition states in hydrogen exchange.Comparison of the 2- : 3-isomer ratios in various substitutions leads to the unexpected conclusion that substitution at the 2-position is subject to steric effects, probably due to the proximity of the sulphur d-orbitals.