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 
• 142653-60-9 1,3-diamino-5-(pentafluorosulfanyl)benzene 
• 1379812-14-2 (2-amino-4-(pentafluorosulfanyl)phenyl)(phenyl)methanone 
• 1440512-05-9 (2-amino-4-(pentafluorosulfanyl)phenyl)(3,4,5-trimethoxyphenyl)methanone 
• 1440512-07-1 9-phenyl-6-(pentafluorosulfanyl)-1,2,3,4-tetrahydroacridine 
• 1440512-08-2 2,4-diphenyl-7-(pentafluorosulfanyl)quinazoline 
• 1379811-92-3 3-phenyl-6-(pentafluorosulfanyl)benzo[c]isoxazole 
• 1379812-13-1 6-(pentafluorosulfanyl)-3-(3-methoxyphenyl)benzo[c]isoxazole 
• 1379812-02-8 6-(pentafluorosulfanyl)-3-(3,4-dimethoxyphenyl)benzo[c]isoxazole 
• 1440512-02-6 6-(pentafluorosulfanyl)-3-(3,4,5-trimethoxyphenyl)benzo[c]isoxazole 
• 1309569-49-0 C₁₃H₁₂F₅NO₂S₂ 
• 1446249-92-8 C₂₀H₁₅ClF₅NO₂S₂ 
• 1446249-98-4 C₂₀H₁₅BrF₅NO₂S₂ 
• 1446249-99-5 C₂₁H₁₈F₅NO₃S₂ 

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.

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.

Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

3-Fluoro-5-nitro-1-(pentafluorosulfanyl)benzene was prepared by three different ways: as a byproduct of direct fluorination of 1,2-bis(3-nitrophenyl)disulfane, by direct fluorination of 4-nitro-1-(pentafluorosulfanyl)benzene, and by fluorodenitration of 3,5-dinitro-1-(pentafluorosulfanyl)benzene. The title compound was subjected to a nucleophilic aromatic substitution of the fluorine atom with oxygen, sulfur and nitrogen nucleophiles affording novel (pentafluorosulfanyl)benzenes with 3,5-disubstitution pattern. Vicarious nucleophilic substitution of the title compound with carbon, oxygen, and nitrogen nucleophiles provided 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzenes substituted in position four.