| 词条 | Fluorobenzene |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443823513 | Name = Fluorobenzene | ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1 = Fluorobenzene-2D-skeletal.png | ImageSizeL1 = 80px | ImageNameL1 = Structure of fluorobenzene | ImageFileR1 = Fluorobenzene-3D-vdW.png | ImageSizeR1 = 120px | ImageNameR1 = Space-filling model of fluorobenzene | IUPACName = Fluorobenzene | OtherNames = Phenyl fluoride Monofluorobenzene |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 9614 | PubChem = 10008 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C11272 | InChI = 1/C6H5F/c7-6-4-2-1-3-5-6/h1-5H | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 5115 | SMILES = Fc1ccccc1 | InChIKey = PYLWMHQQBFSUBP-UHFFFAOYAM | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 16070 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H5F/c7-6-4-2-1-3-5-6/h1-5H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = PYLWMHQQBFSUBP-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 462-06-6 |Section2={{Chembox Properties | Formula = C6H5F | MolarMass = 96.103 | Appearance = Colorless liquid | Density = 1.025 g/mL, liquid | Solubility = low | MeltingPtC = −44 | BoilingPtC = 84 to 85 | BoilingPt_notes = | MagSus = -58.4·10−6 cm3/mol }} |Section3={{Chembox Structure | MolShape = Planar |Section7={{Chembox Hazards | NFPA-H = 1 | NFPA-F = 3 | NFPA-R = 0 | RPhrases = {{R36}}, {{R37}}, {{R38}} | SPhrases = {{S16}}, {{S26}}, {{S36}} |Section8={{Chembox Related | OtherFunction = Chlorobenzene Bromobenzene Iodobenzene | OtherFunction_label = halobenzenes | OtherCompounds = Benzene 1,2-Difluorobenzene }} Fluorobenzene is the chemical compound with the formula C6H5F, often abbreviated PhF. This species is a derivative of benzene, with a single fluorine atom attached. PropertiesIts melting point is -44 °C, which is lower than that of benzene, as a result of the reduced symmetry of the molecule compared to benzene. In contrast, the boiling points of PhF and benzene are very similar, differing by only 4 °C. It is considerably more polar than benzene, with a dielectric constant of 5.42 compared to 2.28 for benzene at 298 K.[1] PreparationOn the laboratory scale, PhF is conveniently prepared by the thermal decomposition of the benzenediazonium tetrafluoroborate[2] PhN2BF4 → PhF + BF3 + N2 According to the procedure, solid [PhN2]BF4 is heated with a flame to initiate an exothermic reaction that affords two volatile products, PhF and BF3, which are readily separated because of their differing boiling points. HistoryPhF was first reported in 1886 by O. Wallach at the University of Bonn, who prepared the compound in two steps, starting also with a phenyldiazonium salt. The diazonium chloride was first converted to its piperidine triazene, which in turn was cleaved using hydrofluoric acid. [PhN2]Cl + 2 C5H10NH → PhN=N-NC5H10 + [C5H10NH2]Cl PhN=N-NC5H10 + 2 HF → PhF + N2 + [C5H10NH2]F Historical note: in Wallach’s era, the element fluorine was symbolized with “Fl”. Thus, his procedure is subtitled “Fluorbenzol, C6H5Fl”.[3] The technical synthesis is by the reaction of cyclopentadiene with difluorocarbene. The initially formed cyclopropane undergoes a ring expansion and subsequent elimination of hydrogen fluoride. ReactionsPhF is a relatively inert compound because the C–F bond is very strong. PhF is a useful solvent for highly reactive species, but a metal complex has been crystallized.[4] See also
References1. ^{{Cite book|title=Table of Dielectric Constants of Pure Liquids|last=|first=|publisher=National Bureau of Standards|year=1951|isbn=|location=|pages=}} {{fluorine compounds}}2. ^{{OrgSynth|author = Flood, D. T.|year = 1943|title=Fluorobenzene|collvol = 2|collvolpages = 295|prep= CV2P0295}}. 3. ^Wallach, O. “Über einen Weg zur leichten Gewinnung organischer Fluorverbindungen” (Concerning a method for easily preparing organic fluorine compounds) Justus Liebig's Annalen der Chemie, 1886, Volume 235, p. 255–271; {{doi|10.1002/jlac.18862350303}} 4. ^R.N. Perutz and T. Braun “Transition Metal-mediated C–F Bond Activation” Comprehensive Organometallic Chemistry III, 2007, Volume 1, p. 725–758; {{doi|10.1016/B0-08-045047-4/00028-5}}. 2 : Fluoroarenes|Phenyl compounds |
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