774-93-6

Usage

Uses

Used in Pharmaceutical Synthesis:
1-BROMO-4-(PENTAFLUOROSULFANYL)BENZENE is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with enhanced properties.
Used in Agrochemical Production:
In the agrochemical industry, 1-BROMO-4-(PENTAFLUOROSULFANYL)BENZENE is utilized as an intermediate, playing a crucial role in the creation of effective and innovative agrochemicals to improve crop protection and yield.
Used in Material Sciences:
1-BROMO-4-(PENTAFLUOROSULFANYL)BENZENE is employed as a building block in the production of advanced materials such as polymers and liquid crystals, where its unique properties contribute to the creation of materials with specific characteristics for various applications.

Upstream product

• 2993-24-0 4-(pentafluorosulfanyl)aniline 
• 5335-84-2 bis(4-bromophenyl)disulfide 
• 15224-36-9 thiophosphoric acid S-(4-bromophenyl) ester O,O'-diethyl ester 
• 5467-74-3 4-Bromophenylboronic acid 
• 106-53-6 para-bromobenzenethiol 
• 2557-81-5 pentafluorosulfanylbenzene 
• 1605274-62-1 4-(pentafluoro-λ⁶-sulfaneyl)benzenediazonium tetrafluoroborate 
• 1062609-73-7 4-bromophenyltetetrafluoro-λ⁶-sulfanyl chloride 
• 2613-27-6 1-nitro-4-(pentafluorosulfanyl)benzene 

Downstream Products

• 401892-84-0 4-(pentafluoro- λ⁶-sulfanyl)benzaldehyde 
• 774-94-7 4-(pentafluoro-λ⁶-sulfaneyl)phenol 
• 401892-85-1 4-(pentafluorosulfaneyl)benzonitrile 
• 845882-19-1 methyl 2-methanesulfonyl-5-methyl-4'-pentafluorosulfanylbiphenyl-4-carboxylate 
• 1286278-34-9 pentafluoro-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-6-sulfane 
• 1126968-86-2 pentafluoro(4-phenoxyphenyl)-λ⁶-sulfane 

Relevant academic research and scientific papers

Validation of Arylphosphorothiolates as Convergent Substrates for Ar-SF 4Cl and Ar-SF 5Synthesis

In this manuscript we describe the oxidative fluorination of aryl phosphorothiolates to access Ar-SF4Cl compounds. These compounds serve as precursors for the highly coveted Ar-SF5 compounds. The use of phosphorothiolates as starting materials permits access to Ar-SF4Cl from a wide variety of available starting materials, namely boronic acids, diazonium salts, aryl iodides, thiophenols, or simple arenes. The protocol has been demonstrated for 10 examples and showed good tolerance to various functional groups. Finally, we demonstrated that AgBF4 can be used as a fluorinating agent, affording good yields of an Ar-SF5.

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.

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.

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.

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.

Pd-catalyzed direct arylation of nitro(pentafluorosulfanyl)benzenes with aryl bromides

Limited methods for the synthesis of SF5-substituted compounds significantly restrict their widespread application. A Pd-catalyzed direct arylation of nitro(pentafluorosulfanyl)benzenes with aryl bromides is reported. This protocol provides a facile and straightforward access to diversified SF5-containing aryl derivatives. The notable features of this reaction are its synthetic simplicity, high reaction efficiency, and good regioselectivity.