106-53-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromothiophenol is used as a reagent for the synthesis of indolyl-3-ethanone-α-thioethers, which are non-toxic antimalarial agents. These compounds exhibit significant anti-malarial activity without causing toxicity to HeLa cell lines, making them a promising option for the development of new treatments against malaria.
In addition to its application in the pharmaceutical industry, 4-Bromothiophenol may also find use in other areas such as chemical synthesis, materials science, and research, due to its unique chemical properties and reactivity.

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

Upstream product

• 722-27-0 bis(4-aminophenyl)disulfide 
• 126253-78-9 S-(4-Bromophenyl)mercapturic acid 
• 5335-84-2 bis(4-bromophenyl)disulfide 
• 3226-41-3 4-bromobenzenediazonium tetrafluoroborate 
• 60775-10-2 (4-bromo-phenyl)-(2,4-dinitro-phenyl)-sulfide 
• 68724-10-7 S-(4-bromo-phenyl)-cysteine 
• 108-98-5 thiophenol 
• 123-75-1 pyrrolidine 
• 154393-31-4 (4-bromo-phenyl)-picryl sulfide 
• 106-37-6 1.4-dibromobenzene 
• 109-73-9 N-butylamine 
• 3406-76-6 (4-bromophenylthio)acetic acid 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 

Downstream Products

• 6631-76-1 Piperidinomethyl-<4-brom-phenyl>-sulfid 
• 53136-21-3 1-benzylsulphanyl-4-bromobenzene 
• 28122-80-7 4-substituted phenylthiol benzoate 
• 63116-04-1 (4-bromo-phenyl)-(2-nitro-phenyl)-disulfide 
• 26732-20-7 4-bromo-(ethylsulfonyl)benzene 
• 223557-20-8 1-bromo-4-(propane-2-sulfonyl)benzene 
• 70399-02-9 1-bromo-4-(1-methylethylsulfonyl)benzene 
• 13735-04-1 3-(4-Bromophenylsulfanyl)propanoic Acid 
• 40897-58-3 1-(4-bromophenyl)-2-(4-nitrophenyl)disulfane 
• 403793-28-2 (4-bromo-phenyl)-butyl sulfone 
• 2393-98-8 1,1’-(methylenedisulfanediyl)bis(4-bromobenzene) 
• 18739-77-0 2-<(4-bromophenyl)thio>propionic acid 
• 856165-22-5 (4-bromo-phenyl)-hexyl sulfone 
• 99853-18-6 2-(4-bromo-phenylsulfanyl)-3-methyl-crotonaldehyde 

Relevant academic research and scientific papers

One-pot synthesis of 6-bromo-4,4-dimethylthiochroman

One-pot synthesis of 6-bromo-4,4-dimethylthiochroman from bromobenzene is reported. The crucial connection between the three steps is that the byproducts in the first two steps are used as the catalyst in the third step. Compared with the previous route, this approach is of low consumption and low pollution.

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.

2-(3-Cyanopropyldimethylsilyl)ethyl as a Polar Sulfur Protecting Group

Organosulfur compounds are ubiquitous in synthetic chemistry, biology and materials chemistry. The reactivity of free sulfhydryls requires their masking in many synthetic strategies. To facilitate the isolation of protected thiols by chromatography, we propose 2-(3-cyanopropyldimethylsilyl)ethyl as a polar protecting group analogue of 2-(trimethylsilyl)ethyl. The masked thiophenol is obtained in two synthetically complementing ways. Either an existing thiophenol is protected, or the protected thiol group is introduced by a cross-coupling reaction. In both cases the required reagents are readily available from inexpensive starting materials. Thiol protection and thiol introduction both tolerate a large variety of functional groups and substitution patterns, and the protected thiophenols are stable toward a broad range of reaction conditions. The stability of the protected derivatives in cross-coupling reactions and the mild reaction conditions for the release of the protecting group further emphasizes the potential of the methodology.

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.

The Chan-Lam reaction of chalcogen elements leading to aryl chalcogenides

A copper-catalyzed chalcogenation of arylboronic acids with elemental sulfur or selenium is established, which provides diaryl disulfides or diaryl monoselenides in moderate to good yields with excellent selectivities, respectively. Moreover, after sequential reduction and coupling with aryl/alkyl iodides in one pot, unsymmetrical monosulfides were obtained in good yields.

Catalytic transfer hydrogenation of aryl sulfo compounds

A new method to reduce aryl sulfo compounds via transfer hydrogenation was investigated, using Pd/C as a catalyst, and 2-propanol or formic acid as hydrogen sources. This new process is simple and clean.

Solvent-free synthesis of thiophenol using uncatalyzed transfer hydrogenation

Clean and sustainable transfer hydrogenation for aryl sulfonamides and sulfonyl chlorides is described. The protocol is chemoselective and uses neither catalyst nor solvent.

Novel one-pot synthesis of thiophenols from related triazenes under mild conditions

In this work, at first, triazenes were synthesized from primary aryl amines. Afterwards, triazenes were converted into the corresponding thiophenols in one-pot using sodium sulfide in acidic media, by in situ generation of diazonium counterion beside hydrogen sulfide as anionic sulfur nucleophile at room temperature. The procedure can be a convenient shortcut for the preparation of thiophenols from primary aryl amines. Georg Thieme Verlag Stuttgart · New York.

Kinetics and mechanism of the aminolysis of O-methyl S-aryl thiocarbonates in acetonitrile

The aminolysis of O-methyl S-aryl thiocarbonates with benzylamines are studied in acetonitrile at -45.0°C. The βX (βnuc) values are in the range 0.62-0.80 with a negative cross-interaction constant, ρXZ = -0.42, which are interpreted to indicate a concerted mechanism. The kinetic isotope effects involving deuterated benzylamine nucleophiles (XC6H 4CH2ND2) are large, kH/kD = 1.29-1.75, suggesting that the N-H(D) bond is partially broken in the transition state by forming a hydrogen-bonded four-center cyclic structure. The concerted mechanism is enforced by the strong push provided by the MeO group which enhances the nucleofugalities of both benzylamine and arenethiolate from the putative zwitterionic tetrahedral intermediate.