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Fluorobenzenes
Fluorobenzenes are a group of aryl fluorides/halobenzenes consisting of one or more fluorine atoms as substituents on a benzene core. They have the formula C6H6–''n''F''n'', where ''n'' = 1–6 is the number of fluorine atoms. Depending on the number of fluorine substituents, there may be several constitutional isomers possible. * Monofluorobenzene * Difluorobenzene ** 1,2-Difluorobenzene ** 1,3-Difluorobenzene ** 1,4-Difluorobenzene * Trifluorobenzene ** 1,2,3-Trifluorobenzene ** 1,2,4-Trifluorobenzene ** 1,3,5-Trifluorobenzene * Tetrafluorobenzene ** 1,2,3,4-Tetrafluorobenzene ** 1,2,3,5-Tetrafluorobenzene ** 1,2,4,5-Tetrafluorobenzene * Pentafluorobenzene * Hexafluorobenzene See also *Chlorobenzenes *Bromobenzenes *Iodobenzenes Iodobenzenes are a group of aryl iodides/halobenzenes consisting of one or more iodine atoms as substituents on a benzene core. They have the formula C6H6–''n''I''n'', where ''n'' = 1–6 is the number of iodine atoms. Depending on the nu ...
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Iodobenzenes
Iodobenzenes are a group of aryl iodides/halobenzenes consisting of one or more iodine atoms as substituents on a benzene core. They have the formula C6H6–''n''I''n'', where ''n'' = 1–6 is the number of iodine atoms. Depending on the number of iodine substituents, there may be several constitutional isomers possible. * Monoiodobenzene * Diiodobenzene ** 1,2-Diiodobenzene ** 1,3-Diiodobenzene ** * ** 1,2,3-Triiodobenzene ** 1,2,4-Triiodobenzene ** 1,3,5-Triiodobenzene * Tetraiodobenzene ** 1,2,3,4-Tetraiodobenzene ** 1,2,3,5-Tetraiodobenzene ** 1,2,4,5-Tetraiodobenzene * Pentaiodobenzene * Hexaiodobenzene See also

*Fluorobenzenes *Chlorobenzenes *Bromobenzenes Iodobenzenes, {{Chemistry index ...
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Bromobenzenes
Bromobenzenes are a group of aryl bromides/halobenzenes consisting of one or more bromine atoms as substituents on a benzene core. They have the formula C6H6–''n''Br''n'', where ''n'' = 1–6 is the number of bromine atoms. Depending on the number of bromine substituents, there may be several constitutional isomers possible. Isomers * Monobromobenzene * Dibromobenzene ** 1,2-Dibromobenzene ** 1,3-Dibromobenzene ** 1,4-Dibromobenzene * Tribromobenzene ** 1,2,3-Tribromobenzene ** 1,2,4-Tribromobenzene ** 1,3,5-Tribromobenzene * Tetrabromobenzene ** 1,2,3,4-Tetrabromobenzene ** 1,2,3,5-Tetrabromobenzene ** 1,2,4,5-Tetrabromobenzene * Pentabromobenzene * Hexabromobenzene Preparation Bromobenzenes may be prepared by electrophilic aromatic bromination of benzene and benzene derivatives, using elemental bromine and the Lewis acid catalyst iron(III) bromide. They may also be prepared from diazonium compounds. Reactions Bromobenzenes may be carboxylated into carboxylic a ...
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Chlorobenzenes
Chlorobenzenes are a group of aryl chlorides/ halobenzenes consisting of one or more chlorine atoms as substituents on a benzene core. They have the formula C6H6–''n''Cl''n'', where ''n'' = 1–6 is the number of chlorine atoms. Depending on the number of chlorine substituents, there may be several constitutional isomers possible. * Monochlorobenzene * Dichlorobenzene ** 1,2-Dichlorobenzene ** 1,3-Dichlorobenzene ** 1,4-Dichlorobenzene * Trichlorobenzene ** 1,2,3-Trichlorobenzene ** 1,2,4-Trichlorobenzene ** 1,3,5-Trichlorobenzene * Tetrachlorobenzene ** 1,2,3,4-Tetrachlorobenzene ** 1,2,3,5-Tetrachlorobenzene ** 1,2,4,5-Tetrachlorobenzene * Pentachlorobenzene * Hexachlorobenzene Hexachlorobenzene, or perchlorobenzene, is an aryl chloride and a six-substituted chlorobenzene with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. Its u ... See also * Fluorobenzenes * Bromobenzen ...
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Hexafluorobenzene
Hexafluorobenzene, HFB or perfluorobenzene is an organofluorine compound with the chemical formula . In this derivative of benzene, all hydrogen atoms have been replaced by fluorine atoms. The technical uses of the compound are limited, although it has some specialized uses in the laboratory owing to distinctive spectroscopic properties. Geometry of the aromatic ring Hexafluorobenzene stands somewhat aside in the perhalogenbenzenes. If a perhalogenated benzene ring were to remain planar, then geometric constraints would force adjacent halogens closer than their associated nonbonding radius. Consequently the benzene ring buckles, reducing ''p''-orbital overlap and aromaticity to avoid the steric clash. Perfluorobenzene is an exception: as shown in the following table, two fluorines are small enough to avoid collision, retaining planarity and full aromaticity. Synthesis The direct synthesis of hexafluorobenzene from benzene and fluorine has not been useful. Instead it is pr ...
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Pentafluorobenzene
Pentafluorobenzene is a synthetic organofluoride compound with the molecular formula . The compound consists of a benzene ring substituted with five fluorine atoms. The substance is a colorless liquid with a boiling point similar to that of benzene.''CRC Handbook of Chemistry and Physics'', 90. Edition, CRC Press, Boca Raton, Florida, 2009, , Section 3, ''Physical Constants of Organic Compounds'', p. 3-414. It is prepared by defluorination of highly fluorinated cyclohexanes over hot nickel or iron. Another method involved dehydrofluorination of polyfluorinated cyclohexane using hot aqueous solution of potassium hydroxide. It has been observed as a degradation by-product of the incineration of polytetrafluoroethylene and of biosolids. Safety According to its Safety Data Sheet (SDS), the chemical is highly flammable, and is harmful if swallowed. The SDS states its "toxicological properties have not been fully investigated". Combustion by-products include hydrogen fluoride. Se ...
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Monofluorobenzene
Fluorobenzene is an aryl fluoride and the simplest of the fluorobenzenes, with the formula C6H5F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds. Preparation PhF was first reported in 1886 by O. Wallach at the University of Bonn, who prepared the compound in two steps. Phenyldiazonium chloride was first converted to a triazene using piperidine: : hN2l + 2 (CH2)5NH → PhN=N-N(CH2)5 + CH2)5NH2l The triazine was then cleaved with hydrofluoric acid: :PhN=N-N(CH2)5 + 2 HF → PhF + N2 + CH2)5NH2 Historical note: in Wallach's era, the element fluorine was symbolized with "Fl". Thus, his procedure is subtitled "Fluorbenzol, C6H5Fl". On the laboratory scale, PhF is prepared by the thermal decomposition of the benzenediazonium tetrafluoroborate: :PhN2BF4 → PhF + BF3 + N2 According to the procedure, solid hN2F4 is heated with a flame to initiate an exothermic reaction, which also affords boron trifluoride and nitro ...
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1,2-Difluorobenzene
1,2-Difluorobenzene, also known as DFB, is an aromatic compound with formula CHF. This colorless flammable liquid is a solvent used in the electrochemical studies of transition metal complexes. Compared to most conventional halogenated aliphatic and aromatic solvents, it possesses an exceptionally high dielectric constant (ε0 = 13.8 at 300 K). Thus, it can be a suitable solvent for cationic, and/or highly electrophilic organometallic complexes. Synthesis Difluorobenzenes can be prepared by the Balz-Schiemann reaction, which entails conversion of diazonium tetrafluoroborate salts to their fluorides. The synthesis of 1,2-difluorobenzene starts with 2- fluoroaniline: : : The syntheses of 1,3- and 1,4-difluorobenzene proceed respectively from 1,3- and 1,4-diaminobenzene, which are doubly diazotized. Laboratory applications Organometallic derivatives of 1,2-difluorobenzene have been well developed. It is found to be a weaker base than benzene. 1,2-Difluorobenzene has been ...
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Halobenzene
Halobenzenes are a group of aryl halides consisting of a benzene ring with halogen atoms as substituents. This includes these groups of halobenzenes: * Fluorobenzenes *Chlorobenzenes * Bromobenzenes *Iodobenzenes Halobenzene may also refer to any of the monosubstituted halobenzenes: *Fluorobenzene *Chlorobenzene *Bromobenzene *Iodobenzene * Astatobenzene Mixed halobenzenes Mixed halobenzenes contain two or more types of halogens bonded to the same benzene ring: * Chlorofluorobenzene * Bromofluorobenzene * Fluoroiodobenzene * Bromochlorobenzene * Chloroiodobenzene * Bromoiodobenzene List of halobenzene derivatives * Haloanilines ** Fluoroaniline ** Chloroaniline ** Bromoaniline ** Iodoaniline * Haloanisoles ** Fluoroanisole ** Chloroanisole ** Bromoanisole ** Iodoanisole * Halobenzaldehydes ** Fluorobenzaldehyde ** Chlorobenzaldehyde ** Bromobenzaldehyde ** Iodobenzaldehyde * Halobenzoic acids ** Fluorobenzoic acid ** Chlorobenzoic acid ** Bromobenzoic acid ** Iodobe ...
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1,2,4,5-Tetrafluorobenzene
Onekama ( ) is a village in Manistee County in the U.S. state of Michigan. The population was 399 at the 2020 census. The village is located on the northeast shore of Portage Lake and is surrounded by Onekama Township. The town's name is derived from ''Ona-ga-maa'', an Anishinaabe word which means "singing water". History The predecessor of the village of Onekama was the settlement of Portage at Portage Point, first established in 1845, at the western end of Portage Lake, at the outlet of Portage Creek. In 1871, when landowners around the land-locked lake became exasperated with the practices of the Portage Sawmill, they took the solution into their own hands and dug a channel through the narrow isthmus, opening a waterway that lowered the lake by and brought it to the same level as Lake Michigan. When this action dried out Portage Creek on May 14, 1871, the settlement, which had only the week before been designated as "Onekama" with a post office under that name, moved to th ...
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