774-94-7

Usage

Uses

Used in Chemical Synthesis:
4-(PENTAFLUOROSULFANYL)PHENOL is used as an intermediate in the synthesis of hexylamides. Its unique SF5 group allows for the formation of active esters, which are crucial in the synthesis process.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(PENTAFLUOROSULFANYL)PHENOL is used as a building block for the development of new drugs. Its unique chemical properties enable the creation of novel drug candidates with potential therapeutic applications.
Used in Material Science:
4-(PENTAFLUOROSULFANYL)PHENOL is utilized in the development of new materials, such as polymers and coatings, due to its specific chemical and physical properties. The SF5 group can impart unique characteristics to these materials, making them suitable for various applications.
Used in Synthesis of Non-metallic Derivatives:
4-(PENTAFLUOROSULFANYL)PHENOL is used as a starting material for the preparation of various non-metallic derivatives of pentafluorothiophenol. These derivatives, which contain sulfur bonded to elements such as boron, carbon, silicon, germanium, phosphorus, arsenic, antimony, sulfur, and chlorine, have potential applications in various fields, including pharmaceuticals, materials science, and chemical synthesis.

InChI:InChI=1/C6H5F5OS/c7-13(8,9,10,11)6-3-1-5(12)2-4-6/h1-4,12H

Upstream product

• 852469-75-1 1-methoxy-4-(pentafluorosulfanyl)-benzene 
• 2557-81-5 pentafluorosulfanylbenzene 
• 1605274-62-1 4-(pentafluoro-λ⁶-sulfaneyl)benzenediazonium tetrafluoroborate 
• 2993-24-0 4-(pentafluorosulfanyl)aniline 
• 326921-47-5 bis-(4-acetoxy-phenyl)-disulfide 
• 15015-57-3 bis(4-hydroxyphenyl)disulfide 
• 67-56-1 methanol 
• 2613-27-6 1-nitro-4-(pentafluorosulfanyl)benzene 
• 774-93-6 1-bromo-4-pentafluorosulfanylbenzene 

Downstream Products

• 852469-75-1 1-methoxy-4-(pentafluorosulfanyl)-benzene 
• 1211514-99-6 2-bromo-1-methoxy-4-(pentafluorosulfanyl)benzene 
• 1159512-26-1 2-nitro-4-(pentafluorosulfanyl)phenol 
• 1159512-27-2 3-amino-4-hydroxy(pentafluorosulfanyl)benzene 

Relevant academic research and scientific papers

Making the SF5 Group More Accessible: A Gas-Reagent-Free Approach to Aryl Tetrafluoro-λ6-sulfanyl Chlorides

Modern pentafluorosulfanyl (SF5) chemistry has an Achilles heel: synthetic accessibility. Herein, we present the first approach to aryl-SF4Cl compounds (key intermediates in state-of-the-art aryl-SF5 synthesis) that overco

METHOD FOR PREPARING A POLYFLUORINATED COMPOUND

The present invention relates to a process for preparing a polyfluorinated compound of formula Ar-Ri(l), wherein Ar-Ri(l) is an aromatic ring system wherein R1 is selected from the group consisting of SF4CI, SF3, SF2CF3, TeFS, TeF4CF3, SeF3, IF2, SeF2CF3, and IF4, X2 is N or CR2, X3 is N or CR 3, X 4 is N or CR 4, X 5 is N or CR 5, X 6 is N or CR 6, and the total number of nitrogen atoms in the aromatic ring system is between 0 and 3, and if X 5 is CR 5 and X 6 is CR 6 R 5 and R 6 may form together a saturated or unsaturated five or six membered ring system comprising one or more nitrogen, wherein said five or six membered ring system may be substituted with one or more residues R 7 said process involving the following reaction step reacting a starting material selected from the group consisting of Ar2S2, Ar2Te2, Ar2Se2, ArSCF3, Arl, ArTeCF3, ArSeCF3, ArSCF3, and ArSCI, wherein Ar has the same definition as above, with trichloroisocyanuric acid (TCICA) of the formula (III) in the presence of the alkali metal fluoride (MF).

Synthesis of 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate and analogs and their application for the preparation of SF5-aromatics

4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate salt was synthesized and isolated. The pentafluorosulfanyl salt was examined in a wide assortment of reactions to form novel SF5-bearing alkenes, alkynes, and biaryl derivatives using Heck-Matsuda, Sonogashira, and Suzuki coupling protocols. Dediazoniation of the salt furnished the corresponding p-SF5—C6H4X,C6H4OS(O)(CF3)═NSO2CF3, and p-SF5—C6H4-NTf2 derivatives. The azide derivative p-SF5—C6H4N3 entered into click chemistry with phenylacetylenes to furnish the corresponding triazoles. Various SF5-bearing alkenes were synthesized by coupling reactions using a metal catalyst. Fluorodediazoniation selectively furnished the fluoro derivative p-SF5—C6H4F. Homolytic dediazoniation gave the unsymmetrical biaryls, thus demonstrating the broad utility of pentafluorosulfanyl diazonium salts as building blocks of SF5-aromatics that are in high demand in many branches of chemistry including biomedicine and materials chemistry.

4-(Pentafluorosulfanyl)benzenediazonium Tetrafluoroborate: A Versatile Launch Pad for the Synthesis of Aromatic SF5 Compounds via Cross Coupling, Azo Coupling, Homocoupling, Dediazoniation, and Click Chemistry

The reagent 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate (1) was synthesized and isolated as a stable salt for the first time; its application in a wide assortment of transformations was subsequently investigated. A series of novel SF5-bearing alkenes, alkynes, and biaryl derivatives were synthesized by employing Heck-Matsuda, Sonogashira, and Suzuki coupling protocols. Dediazoniation with TMSX (X = Hal; N3; and CN) and NH4SCN in [BMIM][BF4] as solvent furnished the corresponding p-SF5-C6H4X derivatives. The azide derivative p-SF5-C6H4N3 entered into click chemistry with phenylacetylenes to furnish the corresponding triazoles. The 4,4′-bis(pentafluorosulfanyl)biphenyl was synthesized by homo-coupling using Pd(OAc)2. The corresponding azo compounds were obtained through azo-coupling with reactive aromatic nucleophiles (1,3-dimethoxybenzene, 1,3,5-trimethoxybenzene, 1,2,4-trimethoxybenzene, aniline and phenol). Fluorodediazoniation in [BMIM][PF6] and [BMIM][BF4] selectively furnished the fluoro derivative p-SF5-C6H4F. Dediazoniation in [BMIM][NTf2] gave p-SF5-C6H4OS(O)(CF3)=NSO2CF3 as the major and p-SF5-C6H4-NTf2 as the minor products. Homolytic dediazoniation in MeCN/NaI gave the unsymmetrical biaryls p-SF5-C6H4-Ar (ArH = mesitylene and p-xylene) along with p-SF5-C6H4I. Analysis of the dediazoniation product mixtures indicated that dediazoniation of p-SF5-C6H4N2+ BF4- in low nucleophilicity, highly ionizing, solvents (TfOH, TFE, HFIP, TFAH) is mainly heterolytic, while in MeOH it is mainly homolytic. The isodesmic reaction p-SF5-C6H4+ + R-C6H5 → SF5-C6H5 + p-R-C6H4+ (with R = NO2, CF3, H) was gauged by DFT at various levels and by PCM.

4-(Pentafluorosulfanyl)benzenediazonium Tetrafluoroborate: A Versatile Launch Pad for the Synthesis of Aromatic SF5 Compounds via Cross Coupling, Azo Coupling, Homocoupling, Dediazoniation, and Click Chemistry

The reagent 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate (1) was synthesized and isolated as a stable salt for the first time; its application in a wide assortment of transformations was subsequently investigated. A series of novel SF5-bearing alkenes, alkynes, and biaryl derivatives were synthesized by employing Heck-Matsuda, Sonogashira, and Suzuki coupling protocols. Dediazoniation with TMSX (X = Hal; N3; and CN) and NH4SCN in [BMIM][BF4] as solvent furnished the corresponding p-SF5-C6H4X derivatives. The azide derivative p-SF5-C6H4N3 entered into click chemistry with phenylacetylenes to furnish the corresponding triazoles. The 4,4′-bis(pentafluorosulfanyl)biphenyl was synthesized by homo-coupling using Pd(OAc)2. The corresponding azo compounds were obtained through azo-coupling with reactive aromatic nucleophiles (1,3-dimethoxybenzene, 1,3,5-trimethoxybenzene, 1,2,4-trimethoxybenzene, aniline and phenol). Fluorodediazoniation in [BMIM][PF6] and [BMIM][BF 4] selectively furnished the fluoro derivative p-SF 5-C6H4F. Dediazoniation in [BMIM][NTf 2] gave p-SF5-C6H4OS(O)(CF 3)=NSO2CF3 as the major and p-SF 5-C6H4-NTf2 as the minor products. Homolytic dediazoniation in MeCN/NaI gave the unsymmetrical biaryls p-SF 5-C6H4-Ar (ArH = mesitylene and p-xylene) along with p-SF5-C6H4I. Analysis of the dediazoniation product mixtures indicated that dediazoniation of p-SF 5-C6H4N2+ BF 4- in low nucleophilicity, highly ionizing, solvents (TfOH, TFE, HFIP, TFAH) is mainly heterolytic, while in MeOH it is mainly homolytic. The isodesmic reaction p-SF5-C6H 4+ + R-C6H5 → SF 5-C6H5 + p-R-C6H4 + (with R = NO2, CF3, H) was gauged by DFT at various levels and by PCM. Copyright

Synthesis of aliphatic sulfur pentafluorides by oxidation of SF5-containing anisole, phenols, and anilines

4-(Pentafluorosulfanyl)catechol, 2-amino-4-(pentafluorosulfanyl)phenol, and 2-amino-5-(pentafluorosulfanyl) phenol undergo oxidation by lead tetraacetate at ambient temperature leading to dearomatization and the formation of SF5-substituted nit

PROCESS FOR THE PREPARATION OF 3- AND 4-(PENTAFLUOROSULFANYL)BENZENES

Process for the preparation of substituted 3- and 4-(pentafluorosulfanyI)benzenes of general formula 3 and 4 by nucleophilic aromatic substitution, where nitrobenzene having pentafiuorosulfanyl group connected in position 3 or 4 is allowed to react in concentration range 0.01 to 8.0 mol.l-1 with compound RY-M+, where R is selected from a group comprising saturated, unsaturated, acyclic, cyclic or aromatic, substituted or unsubstituted carbon chain, Y is the element of VI. B group and M+ is the metal ion, in an organic solvent. The invention includes also further chemical modifications of primary products.

SNAr reactions of nitro-(pentafluorosulfanyl)benzenes to generate SF5 aryl ethers and sulfides

Nucleophilic aromatic substitution of the nitro group of para- and meta-nitro-(pentafluorosulfanyl)benzene with alkoxides and thiolates generates a range of substituted 4- and 3-(pentafluorosulfanyl)benzenes in a single-step reaction.

ORTHO-SUBSTITUTED PENTAFLUOROSULFANYL BENZENES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS SYNTHESIS INTERMEDIATES

The invention relates to pentafluorosulfanyl benzenes of formula (I) in which R1 to R5 have the meanings as cited in the claims, which depict valuable intermediates, e.g. for producing medicaments, diagnostic agents, liquid crystals, pesticides, herbicides, fungicides, nematicides, parasiticides, insecticides, acaricide, arthropodicides and polymers.

ORTHO-SUBSTITUTED PENTAFLUORIDE SULFANYL-BENZENES, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF IN THE FORM OF VALUABLE SYNTHESIS INTERMEDIATE STAGES

The invention relates to pentafluoride-sulfanyl-benzenes of formula (I), wherein groups from R1 to R5 correspond to meanings given in claims and constitute valuable intermediates, for example for producing drugs, diagnosis agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.