827-15-6

Basic information

• Product Name: IODOPENTAFLUOROBENZENE
• Synonyms: Pentafluoroiodobenzene (stabilized with Copper chip);2,3,4,5,6-Pentafluoro-1-iodobenzene;Five-fluoroiodobenzene;Iodoperfluorobenzene 99%;Iodopentafluorobenzene, 99%, stabilised over copper;Pentafluoroiodobenzene, 1-Iodo-2,3,4,5,6-pentafluorobenzene, Perfluoroiodobenzene;Iodopentafluorobenzene, stabilized with copper;Iodopentafluorobenzene SynonyMs: Pentafluoroiodobenzene
• CAS NO: 827-15-6
• Molecular Formula: C₆F₅I
• Molecular Weight: 293.96
• EINECS: 212-565-2
• Product Categories: Aryl;C6;Halogenated Hydrocarbons;organofluorine compounds
• Mol File: 827-15-6.mol
• Article Data: 41

Chemical Properties

• Melting Point: -29°C
• Boiling Point: 161 °C(lit.)
• Flash Point: None
• Appearance: Clear colorless/Liquid
• Density: 2.204 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.33mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 2051549
• CAS DataBase Reference: IODOPENTAFLUOROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: IODOPENTAFLUOROBENZENE(827-15-6)
• EPA Substance Registry System: IODOPENTAFLUOROBENZENE(827-15-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 827-15-6(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Different sources of media describe the Uses of 827-15-6 differently. You can refer to the following data:
1. Iodopentafluorobenzene was used to study the formation of radical ions of iodopentafluorobenzene in aqueous solution . It was used as solvent in a study to determine singlet oxgen lifetimes from phosphorescence decays in halogen substituted perfluorinated solvents by infrared emission spectrometery . It has potential applications in plasma processing industry and in preparation of catalysts .
2. Iodopentafluorobenzene was used to study the formation of radical ions of iodopentafluorobenzene in aqueous solution. It was used as solvent in a study to determine singlet oxgen lifetimes from phosphorescence decays in halogen substituted perfluorinated solvents by infrared emission spectrometery.It has potential applications in plasma processing industry and in preparation of catalysts.

General Description

Iodopentafluorobenzene forms supramolecular complexes with aromatic electron donors by forming halogen bonds to form discrete heterodimeric aggregates.

InChI:InChI=1/C6F5I/c7-1-2(8)4(10)6(12)5(11)3(1)9

Upstream product

• 591-50-4 iodobenzene 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 812-11-3 trifluoromethyliodine difluoride 
• 1109-15-5 tris(pentafluorophenyl)borate 
• 14353-88-9 iodopentafluorobenzene bis(trifluoroacetate) 
• 106-46-7 para-dichlorobenzene 
• 71-43-2 benzene 
• 2314-97-8 iodotrifluoromethane 
• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 91-20-3 naphthalene 
• 98-95-3 nitrobenzene 
• 108-88-3 toluene 
• 95-47-6 o-xylene 
• 98-82-8 Isopropylbenzene 

Downstream Products

• 61794-45-4 3-(Pentafluorphenyl)-prop-2-inol 
• 95123-21-0 5-oxo-5-(pentafluorophenyl)-pentanoic acid methyl ester 
• 129177-95-3 methyl 4-[(pentafluorophenyl)ethynyl]benzoate 
• 1744-45-2 1,2,4,5-tetrafluorobenzene-3-iodo-6-methoxybenzene 
• 3851-64-7 2,3,5,6-Tetrafluorobis(phenylsulphonyl)benzene 
• 135736-89-9 C₁₂F₉IO 
• 1584-03-8 perfluoro-2-methylpent-2-ene 
• 1423-07-0 1-deutero-2,3,4,5,6-pentafluorobenzene 
• 363-72-4 Pentafluorobenzene 
• 118-74-1 hexachlorobenzene 
• 434-90-2 decafluorobiphenyl 
• 14315-34-5 1-iodo nonafluoro cyclohexene 
• 100758-38-1 2,3,3,4,5,6,6-heptafluoro-1-iodo-cyclohexa-1,4-diene 
• 18064-76-1 bis(pentafluorophenyl)telluride 

Relevant articles and documents

One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding

Perfluorinated arenes (benzeneF derivatives, diphenylF, naphthaleneF) were converted into X-perfluoroarenes (X = Br, I) via the developed one-pot protocol based on [Fe(acetylacetonate)3]-assisted C-F functionalization. The syntheses proceed under mild conditions and employ readily available perfluorinated arenes, which are treated with EtMgBr followed by addition of X2/[Fe(acetylacetonate)3] (0.8 mol %); yields range from good to moderate. The σ-hole donor properties of the obtained mono- and di-X-perfluoroarenes and the significance of these species for halogen-bonding-based crystal engineering was illustrated in a series of postsynthetic experiments, all supported by density functional theory (DFT) energy calculations, molecular electrostatic potential (MEP) surface analysis, and the quantum theory of atoms in molecules (QTAIM). These include (i) a solid-state X-ray diffraction study of X-perfluoroarene self-association (dimerization) via iodine σ-hole - electron belt interactions (three X-ray structures) and (ii) verification of X-perfluoroarene σ-hole donor abilities by their interactions with iodides acting as external σ-hole acceptors (five X-ray structures); a Hirshfeld surface analysis was performed for all eight structures.

T -BuONa-mediated direct C-H halogenation of electron-deficient (hetero)arenes

An efficient halogenation of electron-deficient (hetero)arenes is described. The reaction utilizes common t-BuONa as a catalyst (for iodination) or a promoter (for bromination and chlorination), and perfluorobutyl iodide, CBr4 or CCl4 as the readily-available halogenating agents, respectively. The protocol features broad scope, high efficiency, mild conditions and gram scalability. An ionic pathway involving halogen bond formation and halophilic attack is proposed. The utility of the resulting iodinated heteroarenes is demonstrated in visible light-mediated Caryl-Caryl cross-coupling reaction.

Unexpected reactivity of cyclic perfluorinated iodanes with electrophiles

We have found that cyclic perfluorinated iodanes react with electrophiles (E+ = Br, Cl, F, I) to afford perfluorinated E-RF compounds. This reactivity is unexpected since cyclic perfluorinated iodanes are considered as electrophilic reagents that normally react with nucleophiles (e.g. Nu- = SR, OR) to afford Nu-RF products. The utility of this new transformation is demonstrated for a [18F]CF3CF2-containing compound which was prepared from [18F]XeF2 obtained from cyclotron produced [18F]fluoride.