5310-68-9

Basic information

• Product Name: 4-Chlorophenylsulphur pentafluoride
• Synonyms: 4-Chloropentafluorosulphanylbenzene;4-Chlorophenylsulphur pentafluoride;1-Chloro-4-(pentafluorosulphanyl)benzene, 1-Chloro-4-(pentafluorothio)benzene;4-Chlorophenylsulfur Pentafluoride;4-Chloro(pentafluorosulfanyl)benzene;p-Chlorophenylsulfur pentafluoride
• CAS NO: 5310-68-9
• Molecular Formula: C₆H₄ClF₅S
• Molecular Weight: 239
• Mol File: 5310-68-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 77℃ (17 Torr)
• Flash Point: 75°C(lit.)
• Appearance: /
• Refractive Index: 1.4553 (589.3 nm 22℃)
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 4-Chlorophenylsulphur pentafluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorophenylsulphur pentafluoride(5310-68-9)
• EPA Substance Registry System: 4-Chlorophenylsulphur pentafluoride(5310-68-9)

Safety Data

• Hazard Codes: Xi,T
• Hazardous Substances Data: 5310-68-9(Hazardous Substances Data)

Upstream product

• 106-54-7 p-Chlorothiophenol 
• 1605274-62-1 4-(pentafluoro-λ⁶-sulfaneyl)benzenediazonium tetrafluoroborate 
• 1067641-60-4 4-chlorophenyltetetrafluoro-λ⁶-sulfanyl chloride 
• 2613-27-6 1-nitro-4-(pentafluorosulfanyl)benzene 
• 2993-24-0 4-(pentafluorosulfanyl)aniline 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 

Downstream Products

• 165114-87-4 1-chloro-2-nitro-4-(pentafluorosulfanyl)benzene 
• 1422-39-5 pentafluoro(4-fluorophenyl)-λ⁶-sulfane 

Relevant articles and documents

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.

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.

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.