2613-26-5

Basic information

• Product Name: 3-NITROPHENYLSULFUR PENTAFLUORIDE
• Synonyms: SULFUR, PENTAFLUORO(3-NITROPHENYL);3-NITROPHENYLSULPHUR PENTAFLUORIDE;3-NITROPHENYLSULFUR PENTAFLUORIDE;3-NITROBENZENESULFURPENTAFLUORIDE;3-(PENTAFLUOROSULFUR)-NITROBENZENE;1-NITRO-3-(PENTAFLUOROSULFANYL)BENZENE;3-Nitrobenzenesulphur pentafluoride;3-Nitrophenylsulphurpentafluoride96+%
• CAS NO: 2613-26-5
• Molecular Formula: C₆H₄F₅NO₂S
• Molecular Weight: 249.16
• EINECS: 447-600-2
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Nitro CompoundsOrganic Building Blocks;Pentafluorosulfanyls;Nitrogen Compounds;Organic Building Blocks;Sulfur Compounds;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Organic Fluorinated Building Blocks;Pentafluorosulfanyl;Sulfur Compounds
• Mol File: 2613-26-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 0℃
• Boiling Point: 106 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.665 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.475(lit.)
• Water Solubility: Difficult to mix in water.
• BRN: 2699206
• CAS DataBase Reference: 3-NITROPHENYLSULFUR PENTAFLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITROPHENYLSULFUR PENTAFLUORIDE(2613-26-5)
• EPA Substance Registry System: 3-NITROPHENYLSULFUR PENTAFLUORIDE(2613-26-5)

Safety Data

• Hazard Codes: Xi,T,Xn
• Statements: 34-36/37-20/22
• Safety Statements: 26-36/37/39-45
• RIDADR: 2810
• WGK Germany: 3
• TSCA: No
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2613-26-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to tan liquid

Uses

It has a wide range of applications as a fluorinating agent. g. It is a convenient alternative to current fluorinating agents for use in the synthesis of specialty chemicals and intermediates, such as pharmaceuticals, agrochemicals and electronics chemicals.

InChI:InChI=1/5C6H5NO2S.5FH/c5*8-7(9)5-2-1-3-6(10)4-5;;;;;/h5*1-4,10H;5*1H/q5*+1;;;;;/p-5

Upstream product

• 537-91-7 bis(3-nitrophenyl) disulfide 
• 2993-24-0 4-(pentafluorosulfanyl)aniline 
• 1605274-62-1 4-(pentafluoro-λ⁶-sulfaneyl)benzenediazonium tetrafluoroborate 
• 2557-81-5 pentafluorosulfanylbenzene 
• 654671-65-5 2,4,5-trichloropentafluorosulfanylcyclohexane 
• 89415-83-8 4,5-dichlorocyclohexene 
• 1165952-92-0 cyclohexa-1,4-diene 
• 35964-48-8 1,1'-disulphanediylbis(4-chloro-3-nitrobenzene) 

Downstream Products

• 1736-99-8 (3-acetamidophenyl)sulfurpentafluoride 
• 142653-59-6 1,3-dinitro-5-(pentafluorosulfanyl)benzene 
• 349-78-0 3-nitrobenzene-1-sulfonyl fluoride 
• 1621957-58-1 1-(fluorosulfonyl)-3,5-dinitrobenzene 

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.

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.