286947-68-0

Usage

Uses

Used in Pharmaceutical Industry:
1-IODO-4-(PENTAFLUOROSULFANYL)BENZENE is used as a key intermediate in the synthesis of new pharmaceuticals, contributing to the development of innovative drugs with enhanced properties and therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, 1-IODO-4-(PENTAFLUOROSULFANYL)BENZENE is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides, to improve their efficacy and selectivity in crop protection.
Used in Advanced Materials Industry:
1-IODO-4-(PENTAFLUOROSULFANYL)BENZENE is employed as a component in the creation of advanced materials, including polymers and composites, due to its unique chemical properties that can enhance material performance and functionality.
Used as a Reagent in Organic Chemistry:
1-IODO-4-(PENTAFLUOROSULFANYL)BENZENE is used as a reagent in various chemical reactions, facilitating the synthesis of complex organic compounds and contributing to the advancement of organic chemistry research.

InChI:InChI=1/C6H4F5IS/c7-13(8,9,10,11)6-3-1-5(12)2-4-6/h1-4H

Upstream product

• 2993-24-0 4-(pentafluorosulfanyl)aniline 
• 774-93-6 1-bromo-4-pentafluorosulfanylbenzene 
• 2557-81-5 pentafluorosulfanylbenzene 
• 1605274-62-1 4-(pentafluoro-λ⁶-sulfaneyl)benzenediazonium tetrafluoroborate 
• 100-66-3 methoxybenzene 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 106-42-3 para-xylene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 2613-27-6 1-nitro-4-(pentafluorosulfanyl)benzene 

Downstream Products

• 1046446-99-4 pentafluoro(4-vinylphenyl)-λ⁶-sulfane 
• 401892-84-0 4-(pentafluoro- λ⁶-sulfanyl)benzaldehyde 
• 1401165-57-8 6-((4-(pentafluorothio)phenyl)ethynyl)picolinaldehyde 
• 1416985-68-6 C₁₈H₂₇F₅OSSi 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 55606-94-5 1,4-bis(4'-fluorophenyl)-buta-1,3-diyne 
• 134889-83-1 1,4-dicyclopentylbuta-1,3-diyne 
• 183210-84-6 1,4-bis(4-tert-butylphenyl)buta-1,3-diyne 
• 1286278-34-9 pentafluoro-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-6-sulfane 
• 1606141-18-7 1-pentafluorosulfanyl-4-(trifluoromethylthio)ethynylbenzene 
• 832-32-6 4-(pentafluoro-λ⁶-sulphanyl)benzoic acid 

Relevant academic research and scientific papers

Development of boron-cluster-based progesterone receptor antagonists bearing a pentafluorosulfanyl (SF5) group

The progesterone receptor (PR) plays an important role in various physiological processes, especially in the female reproductive system, and abnormalities of PR function are associated with several diseases, including some types of cancer. Non-steroidal P

Studies of halogen bonding induced by pentafluorosulfanyl aryl iodides: A potential group of halogen bond donors in a rational drug design

The activation of halogen bonding by the substitution of the pentafluoro-λ6-sulfanyl (SF5) group was studied using a series of SF5-substituted iodobenzenes. The simulated electrostatic potential values of SF5-substituted iodobenzenes, the ab initio molecular orbital calculations of intermolecular interactions of SF5-substituted iodobenzenes with pyridine, and the 13C-NMR titration experiments of SF5-substituted iodobenzenes in the presence of pyridine or tetra (n-butyl) ammonium chloride (TBAC) indicated the obvious activation of halogen bonding, although this was highly dependent on the position of SF5-substitution on the benzene ring. It was found that 3,5-bis-SF5-iodobenzene was the most effective halogen bond donor, followed by o-SF5-substituted iodobenzene, while the m- and p-SF5 substitutions did not activate the halogen bonding of iodobenzenes. The similar ortho-effect was also confirmed by studies using a series of nitro (NO2)-substituted iodobenzenes. These observations are in good agreement with the corresponding Mulliken charge of iodine. The 2:1 halogen bonding complex of 3,5-bis-SF5-iodobenzene and 1,4-diazabicyclo[2.2.2]octane (DABCO) was also confirmed. Since SF5-containing compounds have emerged as promising novel pharmaceutical and agrochemical candidates, the 3,5-bis-SF5-iodobenzene unit may be an attractive fragment of rational drug design capable of halogen bonding with biomolecules.

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides

A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.

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.

DIARYLIODONIUM SALT

PROBLEM TO BE SOLVED: To provide a compound that allows easy introduction of a pentafluorosulfanylaryl group into a compound of interest. SOLUTION: A diaryliodonium salt is represented by the general formula (d) in the figure. (In the formula, k is 1 or 2, R1 is an alkyl group having 1 or 2 carbon atoms, m is an integer from 0 to 4, R2 is a straight or branched alkyl group having 1 to 4 carbon atoms, n is an integer from 0 to 5, and A- is a counter anion.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT

DIARYLIODONIUM SALT

Provided is a compound that allows easy introduction of a pentafluorosulfanylaryl group into a compound of interest. A diaryliodonium salt is represented by the general formula (d) shown below: In this formula, k is 1 or 2, R1 is an alkyl group having 1 or 2 carbon atoms, m is an integer of 0 to 4, R2 is a straight or branched alkyl group having 1 to 4 carbon atoms, n is an integer of 0 to 5, and A? is a counter anion.

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B2pin2, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.

Synthesis of Diaryliodonium Salts Having Pentafluorosulfanylarenes and Their Application to Electrophilic Pentafluorosulfanylarylation of C-, O-, N-, and S-Nucleophiles

Novel reagents for the electrophilic introduction of pentafluorosulfanyl (SF5) arenes into target molecules are disclosed. Unsymmetrical diaryliodonium salts 1 having SF5-arenes were synthesized by a one-pot process from iodo-SF5-benzenes 2 in good yields. The SF5-aryliodonium salts 1 were found to be efficient for the electrophilic SF5-arylation of carbon and heterocentered nucleophiles to furnish the corresponding substituted SF5-arenes in good to high yields.

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

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.