2993-22-8

Usage

Uses

Used in Chemical Synthesis:
3-AMINOPHENYLSULFUR PENTAFLUORIDE is used as a reagent for the reduction of pentafluoroaniline (PFA), leading to rapid fluoride elimination and the formation of the aminotetrafluorophenyl radical. This radical can then participate in homolytic reactions with other aromatic compounds, allowing for the synthesis of novel and complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-AMINOPHENYLSULFUR PENTAFLUORIDE is used as an intermediate for the synthesis of various drugs and drug candidates. Its unique chemical properties enable the development of new compounds with potential therapeutic applications.
Used in Material Science:
3-AMINOPHENYLSULFUR PENTAFLUORIDE is used as a building block for the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. These materials can be applied in various fields, including electronics, coatings, and adhesives.
Used in Research and Development:
3-AMINOPHENYLSULFUR PENTAFLUORIDE is used as a research tool for studying the properties and reactivity of perfluoroaromatic compounds. Its unique structure allows scientists to gain insights into the behavior of these compounds and develop new strategies for their synthesis and application.

InChI:InChI=1/C6H6F5NS/c7-13(8,9,10,11)6-3-1-2-5(12)4-6/h1-4H,12H2

Upstream product

• 654671-65-5 2,4,5-trichloropentafluorosulfanylcyclohexane 
• 2557-81-5 pentafluorosulfanylbenzene 
• 89415-83-8 4,5-dichlorocyclohexene 
• 1165952-92-0 cyclohexa-1,4-diene 
• 2613-26-5 3-nitrophenylsulfur pentafluoride 

Downstream Products

• 2402-76-8 1-(dimethylamino)-3-(pentafluorosulfanyl)benzene 
• 286947-67-9 pentafluoro(3-iodophenyl)-λ⁶-sulfane 
• 1736-99-8 (3-acetamidophenyl)sulfurpentafluoride 
• 672-31-1 3-hydroxy(pentafluorosulfanyl)benzene 
• 108-95-2 phenol 
• 845882-12-4 N-methanesulfonyl-(3-pentafluorosulfanylphenyl)methanesulfonamide 
• 833-96-5 3-(pentafluoro-λ⁶-sulphanyl)benzoic acid 
• 401892-82-8 3-(pentafluorosulfaneyl)benzonitrile 
• 1286278-35-0 4,4,5,5-tetramethyl-2-(3-(pentafluoro-λ6-sulfaneyl)phenyl)-1,3,2-dioxaborolane 
• 2557-81-5 pentafluorosulfanylbenzene 

Relevant academic research and scientific papers

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.

Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects

Direct fluorination of ortho-, meta- and para-substituted aromatic thiols and disulfides using elemental fluorine afforded substituted (pentafluorosulfanyl)benzenes. This work thus represents the first study of the scope and limitation of direct fluorination for the synthesis of new SF5-containing building blocks. Fluorinations in batch and flow modes were compared. A comprehensive computational study was carried out employing density functional and wave function methods to elucidate the reaction mechanism of the transformation of ArSF3 into ArSF5. Eliminating various nonradical pathways, it has been shown that the reaction proceeds by a radical mechanism, initiated by the attack of the F. on the ArSF3 moiety, propagated via an almost barrierless F2+ArSF4 .→ArSF5+F. step and terminated by the ArSF4 .+F.→ArSF5. Most of the calculated data are in very good agreement with experimental observations concerning the ortho-substituent effect on the reaction rates and yields.

METHOD FOR PRODUCING NITROGEN-CONTAINING PENTAFLUOROSULFANYLBENZENE COMPOUND

A method for producing a nitrogen-containing pentafluorosulfanylbenzene compound of formula (2a) or (2b): (wherein R1 a hydrogen atom or a hydrocarbon group; Z is an aryl group linked to a carbonyl group; Y is a group of formula (Y1), (Y2), (Y3), or (Y4); R2 is a hydrogen atom or a hydrocarbon group) the method comprising reacting a halogeno-pentafluorosulfanylbenzene compound of formula (1) with a nitrogenous nucleophile: (wherein X is a halogen atom; n is an integer of 1 to 5; R1 is as defined above).

The pentafluorosulfanyl group in cannabinoid receptor ligands: Synthesis and comparison with trifluoromethyl and tert-butyl analogues

An array of cannabinoid ligands, bearing meta- and para-substituted pentafluorosulfanyl (SF5) aniline groups in position 3 of the pyrazole ring, was efficiently synthesised and compared with the exact trifluoromethyl and tert-butyl analogues. In general, the SF5 substituted ligands showed higher lipophilicity (i.e. logP values) than the CF3 counterparts and lower lipophilicity than the tert-butyl ones. In terms of pharmacological activity, SF5 pyrazoles generally showed slightly higher or equivalent CB1 receptor affinity (Ki), always in the nanomolar range, and selectivity towards the CB2 relative to both CF3 and tert-butyl analogues. Functional β-arrestin recruitment assays were used to determine equilibrium dissociation constants (Kb) and showed that all of the tested SF 5 and CF3 compounds are CB1 neutral antagonists. These results confirm the possibility of successfully using an aromatic SF5 group as a stable, synthetically accessible and effective bioisosteric analogue of the electron-withdrawing CF3 group, and possibly also of bulky aliphatic groups, for drug discovery and development applications. This journal is the Partner Organisations 2014.

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

Synthesis of pentafluorosulfanyl-containing indoles and oxindoles

Vicarious nucleophilic substitution (VNS) of 3- and 4- nitro(pentafluorosulfanyl)benzenes with phenoxyacetonitrile followed by catalytic hydrogenation provided a two-step, atom-economical synthetic route to 6- and 5-(pentafluoro-sulfanyl)-1H-indoles. The

Preparations and reactions of SF5-substituted aryl and heteroaryl derivatives via Mg and Zn organometallics

Polyfunctional SF5-substituted cycles: Several organometallic sequences using zinc, copper, and magnesium intermediates were developed to prepare a broad range of SF5-substituted aromatic and heterocyclic compounds of potential interest for pharmaceutical applications. Copyright

Substituted imidazoline-2,4-diones, process for preparation thereof, medicaments comprising these compounds and use thereof

The invention relates to compounds of formula (I) wherein the groups R and R′, A, D, E, G, L, p and R1 to R10 have the stated meanings and to their physiologically compatible salts. Said compounds are suitable, for example, as anti-obesity drugs.

Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, process for preparing them, medicaments comprising these compounds, and their use

This invention relates to arylaminoaryl-alkyl-substituted imidazolidone-2,4-diones of formula (I) and also to their physiologically tolerated salts: Wherein R, R′, R1 to R10, A, D, E, G, L and p are as defined herein. The invention also relates to processes for preparing them, pharmaceutical compositions comprising them and their therapeutic use. The compounds are suitable, for example, as anti-obesity drugs and for treating cardiometabolic syndrome.

A new synthesis of pentafluorosulfanylbenzene

(Equation Presented) A new and convenient three-step synthesis of pentafluorosulfanylbenzene from 1,4-cyclohexadiene with an overall yield of >70% is reported along with a number of derivatization reactions.