672-30-0

Usage

Uses

Used in Pharmaceutical Industry:
1-BROMO-3-(PENTAFLUOROSULFANYL)BENZENE is used as a reactant in the preparation of blue-to-green emitting neutral Ir(III) complexes bearing pentafluorosulfanyl groups. These complexes have potential applications in the development of new pharmaceutical compounds and drug delivery systems.
Used in Chemical Synthesis:
1-BROMO-3-(PENTAFLUOROSULFANYL)BENZENE can be utilized as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure and reactivity make it a valuable building block for the development of new molecules with desired properties.
Used in Research and Development:
Due to its unique chemical properties, 1-BROMO-3-(PENTAFLUOROSULFANYL)BENZENE can be employed in research and development projects aimed at understanding the behavior of pentafluorosulfanyl-containing compounds and their potential applications in various fields, such as materials science, catalysis, and environmental chemistry.

InChI:InChI=1/C6H4BrF5S/c7-5-2-1-3-6(4-5)13(8,9,10,11)12/h1-4H

Upstream product

• 2993-22-8 3-pentafluorosulfuraniline 
• 2557-81-5 pentafluorosulfanylbenzene 
• 1165952-92-0 cyclohexa-1,4-diene 
• 89415-83-8 4,5-dichlorocyclohexene 
• 654671-65-5 2,4,5-trichloropentafluorosulfanylcyclohexane 
• 2613-26-5 3-nitrophenylsulfur pentafluoride 
• 1062609-77-1 m-bromophenylsulfur chlorotetrafluoride 
• 19742-90-6 1-bromo-3-[(3-bromophenyl)disulfanyl]benzene 
• 6320-01-0 3-Bromothiophenol 

Downstream Products

• 159896-31-8 1-[3-(pentafluorosulfanyl)phenyl]ethanone 
• 159727-25-0 2-bromo-4-(pentafluoro-λ⁶-sulfanyl)aniline 
• 401892-80-6 3-(pentafluorosulfanyl)benzaldehyde 

Relevant academic research and scientific papers

AgBF4-Mediated Chlorine-Fluorine Exchange Fluorination for the Synthesis of Pentafluorosulfanyl (Hetero)arenes

We report a new protocol to form pentafluorosulfanyl (hetero)arenes via chlorine-fluorine exchange of (hetero)aryl tetrafluorosulfanyl chlorides by AgBF4. The method enables access to electron-deficient pentafluorosulfanyl(hetero)arenes, which are targets that are difficult to synthesize. Two advantages of AgBF4 are its ease of handling and stability. This would be a general transformation protocol.

METHOD OF PRODUCING PENTAFLUOROSULFANYL AROMATIC COMPOUND

A method of producing a pentafluorosulfanyl aromatic compound is provided. A method of producing a pentafluorosulfanyl aromatic compound represented by general formula (3): [in-line-formulae]Ar—(SF5)k??(3)[/in-line-formulae]where Ar is a substituted or an unsubstituted aryl group or heteroaryl group, and k is an integer of 1 to 3;the method includes reacting IF5 with a halotetrafluorosulfanyl aromatic compound represented by general formula (2): [in-line-formulae]Ar—(SF4Hal)k??(2)[/in-line-formulae]where Ar and k are defined as above; and Hal is a Cl group, a Br group, or an I group.

IF5 affects the final stage of the Cl-F exchange fluorination in the synthesis of pentafluoro-λ6-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents

A difficult chlorine-fluorine (Cl-F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-λ6-sulfanyl-(hetero)arenes having electron-withdrawing substituents has now been elucidated through the use of iodine pentafluoride. A major side-reaction of C-S bond cleavage was sufficiently inhibited by the potential interaction between F and I with a halogen bonding.

Silver-induced self-immolative Cl-F exchange fluorination of arylsulfur chlorotetrafluorides: Synthesis of arylsulfur pentafluorides

A novel strategy for the synthesis of arylsulfur pentafluorides by silver carbonate-induced Cl-F exchange fluorination of arylsulfur chlorotetrafluorides is reported. This fluorination does not require any exogenous fluoride sources. Rather, the reaction proceeds via the self-immolation of the substrate Ar-SF4Cl.

Ir-catalyzed preparation of SF5-substituted potassium aryl trifluoroborates via C-H borylation and their application in the Suzuki-Miyaura reaction

The preparation of new pentafluorosulfanyl-substituted potassium aryltrifluoroborates via Ir-catalyzed C-H borylation is reported. The utility of these novel building blocks was demonstrated in the Suzuki-Miyaura cross-coupling reaction, giving access to

Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of "super-trifluoromethyl" arene chemistry and its industry

Various arylsulfur pentafluorides, ArSF5, have long been desired in both academic and industrial areas, and ArSF5 compounds have attracted considerable interest in many areas such as medicines, agrochemicals, and other new materials, since the highly stable SF5 group is considered a "super-trifluoromethyl group" due to its significantly higher electronegativity and lipophilicity. This article describes the first practical method for the production of various arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides), from the corresponding diaryl disulfides or aryl thiols. The method consists of two steps: (Step 1) treatment of a diaryl disulfide or an aryl thiol with chlorine in the presence of an alkali metal fluoride, and (step 2) treatment of the resulting arylsulfur chlorotetrafluoride with a fluoride source, such as ZnF2, HF, and Sb(III/V) fluorides. The intermediate arylsulfur chlorotetrafluorides were isolated by distillation or recrystallization and characterized. The aspects of these new reactions are revealed and reaction mechanisms are discussed. As the method offers considerable improvement over previous methods in cost, yield, practicality, applicability, and large-scale production, the new processes described here can be employed as the first practical methods for the economical production of various arylsulfur pentafluorides and their higher homologues, which could then open up a new era of "super-trifluoromethyl" arene chemistry and its applications in many areas.

METHODS FOR PRODUCING ARYLSULFUR PENTAFLUORIDES

Novel methods for preparing arylsulfur pentafluorides are disclosed. Arylsulfur halotetrafluoride is reacted with a fluoride source under hydrous conditions to form an arylsulfur pentafluoride. The purification method is also disclosed.

PROCESS FOR PRODUCING ARYLSULFUR PENTAFLUORIDES

Novel processes for preparing arylsulfur pentafluorides are disclosed. Processes include reacting at least one aryl sulfur compound with a halogen and a fluoro salt to form an arylsulfur halotetrafluoride. The arylsulfur halotetrafluoride is reacted with a fluoride source to form a target arylsulfur pentafluoride.

Synthesis and characterisation of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives. X-ray structure of 3-SF5-C6H4-COOH

The high yield synthesis of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives is described starting from the NO2-derivatives, which are reduced to the corresponding anilines. Then the NH2- group is converted to bromide and subsequently to the HC{double bond, long}O moiety. The benzaldeydes are then oxidised to the corresponding benzoic acids. The X-ray structure of 3-SF5-C6H4-COOH is also reported.

The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine

The trifluoromethyl group of fluoxetine 1 and fenfluramine and norfenfluramine, 2 and 3, was substituted by the pentafluorosulfanyl group. On examination of the efficacy of the pentafluorosulfanyl containing compounds as inhibitors of 5-hydroxytryptamine receptors, it was found that substitution could lead to enhanced selectivity and in the case of the pentafluorosulfanyl analog of fenfluramine, 18, it significantly enhanced potency against the 5-HT2b, 5-HT2c, and 5-HT6 receptors.