フルオロベンゼン、フッ化ベンゼン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/02/21 02:51:42」(JST)
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| Fluorobenzene |
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Other names
Phenyl fluoride
Monofluorobenzene
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| Identifiers |
| CAS number |
462-06-6 Y |
| PubChem |
10008 |
| ChemSpider |
9614 Y |
| KEGG |
C11272 Y |
| ChEBI |
CHEBI:5115 Y |
| ChEMBL |
CHEMBL16070 Y |
| Jmol-3D images |
Image 1 |
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InChI=1S/C6H5F/c7-6-4-2-1-3-5-6/h1-5H Y
Key: PYLWMHQQBFSUBP-UHFFFAOYSA-N Y
InChI=1/C6H5F/c7-6-4-2-1-3-5-6/h1-5H
Key: PYLWMHQQBFSUBP-UHFFFAOYAM
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| Properties |
| Molecular formula |
C6H5F |
| Molar mass |
96.103 |
| Appearance |
Colorless liquid |
| Density |
1.025 g/mL, liquid |
| Melting point |
−44 °C
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| Boiling point |
84–85 °C
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| Solubility in water |
low |
| Structure |
| Molecular shape |
Planar |
| Hazards |
| R-phrases |
R36, R37, R38 |
| S-phrases |
S16, S26, S36 |
| NFPA 704 |
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| Related compounds |
| Related halobenzenes |
Chlorobenzene
Bromobenzene
Iodobenzene |
| Related compounds |
Benzene
1,2-Difluorobenzene |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
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. Its melting point is -44 °C, which is lower than that of benzene, indicative of the remarkable effect of fluorination on the intermolecular interactions as seen throughout organofluorine chemistry. In contrast, the boiling points of PhF and benzene differ by only 4 °C.
Preparation
On the laboratory scale, PhF is conveniently prepared by the thermal decomposition of the benzenediazonium tetrafluoroborate[1]
- 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.
PhF 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 piperidinide, 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
An interesting historical note: in Wallach’s era, the element fluorine was symbolized with “Fl”. Thus, his procedure is subtitled “Fluorbenzol, C6H5Fl”.[2]
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.
Reactions
PhF 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.[3]
-
Structure of [(C
5Me
5)
2Ti(FC
6H
5)]
+, a coordination complex of fluorobenzene.
Fluorination of fluorobenzene gives mainly 1,2-difluorobenzene.
References
- ^ Flood, D. T. (1943), "Fluorobenzene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0295; Coll. Vol. 2: 295.
- ^ 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
- ^ 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.
English Journal
- Use of molecular modeling aided design to dial out hERG liability in adenosine A2A receptor antagonists.
- Deng Q1, Lim YH2, Anand R3, Yu Y3, Kim JH3, Zhou W2, Zheng J2, Tempest P4, Levorse D5, Zhang X6, Greene S6, Mullins D6, Culberson C7, Sherborne B8, Parker EM9, Stamford A2, Ali A2.
- Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2015 Aug 1;25(15):2958-62. doi: 10.1016/j.bmcl.2015.05.036. Epub 2015 May 21.
- Molecular modeling was performed on a triazolo quinazoline lead compound to help develop a series of adenosine A2A receptor antagonists with improved hERG profile. Superposition of the lead compound onto MK-499, a benchmark hERG inhibitor, combined with pKa calculations and measurement, identified t
- PMID 26048804
- Ruthenium-catalyzed nucleophilic fluorination of halobenzenes.
- Konovalov AI1, Gorbacheva EO, Miloserdov FM, Grushin VV.
- Chemical communications (Cambridge, England).Chem Commun (Camb).2015 Jul 29. [Epub ahead of print]
- The first π-coordination-catalyzed nucleophilic fluorination of unactivated aryl halides has been demonstrated. Chlorobenzene reacts with alkali metal fluorides (CsF, KF) in the presence of a Cp*Ru catalyst at 120-180 °C to give fluorobenzene.
- PMID 26219388
- Synthesis, crystal structure, biological activity and theoretical calculations of novel isoxazole derivatives.
- Jin RY1, Sun XH2, Liu YF3, Long W4, Chen B3, Shen SQ5, Ma HX6.
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Jul 10;152:226-232. doi: 10.1016/j.saa.2015.07.057. [Epub ahead of print]
- Series of isoxazole derivatives were synthesized by substituted chalcones and 2-chloro-6-fluorobenzene formaldehyde oxime with 1,3-dipolar cycloaddition. The target compounds were determined by melting point, IR, 1H NMR, elemental analyses and HRMS. The crystal structure of compound 3a was detected
- PMID 26218917
Japanese Journal
- Oral glucosylceramide reduces 2,4-dinitrofluorobenzene induced inflammatory response in mice by reducing TNF-alpha levels and leukocyte infiltration.
- Mechanistic Studies on Fluorobenzene Synthesis from 1,1-Difluorocyclohexane via Pd-Catalyzed Dehydrofluoro-Dehydrogenation
- Bulletin of the Chemical Society of Japan 84(3), 333-340, 2011-03-15
- NAID 10028046510
- キノリニウムイオンを触媒として用いた芳香族化合物の光フッ素化反応
Related Links
- Sigma-Aldrich offers Aldrich-F6001, Fluorobenzene for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Technical Service: Our team of scientists has experience in all areas ...
- Benzene, fluoro-Formula: C 6 H 5 F Molecular weight: 96.1023 IUPAC Standard InChI: InChI=1S/C6H5F/c7-6-4-2-1-3-5-6/h1-5H Download the identifier in a file. IUPAC Standard InChIKey: PYLWMHQQBFSUBP-UHFFFAOYSA-N ...
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