Tetrabromo-o-xylene
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Tetrabromo-o-xylene
α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C6H4(CHBr2)2. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prepared by the photochemical reaction of o-xylene with elemental bromine: : Reaction of α,α,α',α'-tetrabromo-o-xylene with sodium iodide affords α,α'-dibromo-o- xylylene, which can be trapped with dienophiles to give naphthylene. In the absence of trapping agents, the xylylene relaxes to α,α'-dibromobenzocyclobutane: : : Cycloadditions of these xylylenes provides a pathway to acene In organic chemistry, the acenes or polyacenes are a class of organic compounds and polycyclic aromatic hydrocarbons made up of benzene () rings which have been linearly fused. They follow the general molecular formula . The larger represent ...s. References {{Reflist Organobromides ...
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Xylylene
In organic chemistry, a xylylene (sometimes quinone-dimethide) is any of the constitutional isomers having the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. Arene substitution patterns, ''ortho''- and ''para''-xylylene are best known, although neither is stable in solid or liquid form. The ''meta'' form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, such as tetracyanoquinodimethane and the xylylene dichlorides. p-Xylylene ''p''-Xylylene forms upon pyrolysis of ''p''-xylene or, more readily, the α-substituted derivatives. ''p''-Xylylene Dimer (chemistry), dimerizes with moderate efficiency to give ''p''-cyclophane: Further heating of the ''p''-cyclophane gives Parylene, poly(''para''-xylylene). o-Xylylenes o-Xylylenes (''o''-quinodimethanes) are often generated in situ, e.g., by the pyrolysis of the corresponding sulfone. Another met ...
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Organobromine Compound
Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. General properties Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Carbon–haloge ...
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Photochemical Reaction
Organic photochemistry encompasses organic reactions that are induced by the action of light. The absorption of ultraviolet light by organic molecules often leads to reactions. In the earliest days, sunlight was employed, while in more modern times ultraviolet lamps are employed. Organic photochemistry has proven to be a very useful synthetic tool. Complex organic products can be obtained simply. History Early examples were often uncovered by the observation of precipitates or color changes from samples that were exposed to sunlights. The first reported case was by Ciamician that sunlight converted santonin to a yellow photoproduct: An early example of a precipitate was the photodimerization of anthracene, characterized by Yulii Fedorovich Fritzsche and confirmed by Elbs. Similar observations focused on the dimerization of cinnamic acid to truxillic acid. Many photodimers are now recognized, e.g. pyrimidine dimer, thiophosgene, diamantane. Another example was uncovered by ...
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O-xylene
''o''-Xylene (''ortho''-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of ''m''-xylene and ''p''-xylene, the mixture being called xylene or xylenes. ''o''-Xylene is a colourless slightly oily flammable liquid. Production and use Petroleum contains about one weight percent xylenes. Most ''o''-xylene is produced by cracking petroleum, which affords a distribution of aromatic compounds, including xylene isomers. ''m''-Xylene is isomerized to ''o''-xylene. Net production was approximately 500,000 tons in the year 2000. ''o''-Xylene is largely used in the production of phthalic anhydride, which is a precursor to many materials, drugs, and other chemicals. Related to their easy oxidation, the methyl groups are susceptible to halogenation. When treated with elemental bromine Bromine is a chemical element; it has chemical ...
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Bromine
Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig (in 1825) and Antoine Jérôme Balard (in 1826), its name was derived , referring to its sharp and pungent smell. Elemental bromine is very reactive and thus does not occur as a free element in nature. Instead, it can be isolated from colourless soluble crystalline mineral halide Ionic salt, salts analogous to table salt, a property it shares with the other halogens. While it is rather rare in the Earth's crust, the high solubility of the bromide ion (Br) has caused its Bromine cycle, accumulation in the oceans. Commercially the element is easily extracted from brine evaporation ponds, mostly in the United States and Israel. The mass of bromine in the oce ...
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Cycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the Multiplicity (chemistry)#Molecules, bond multiplicity". The resulting reaction is a cyclization reaction. Many but not all cycloadditions are Concerted reaction, concerted and thus pericyclic. Nonconcerted cycloadditions are not pericyclic. As a class of addition reaction, cycloadditions permit carbon–carbon bond formation without the use of a nucleophile or electrophile. Cycloadditions can be described using two systems of notation. An older but still common notation is based on the size of linear arrangements of atoms in the reactants. It uses parentheses: where the variables are the numbers of linear atoms in each reactant. The product is a cycle of size . In this system, the standard Diels-Alder reaction is a (4 + 2)-cyc ...
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Acene
In organic chemistry, the acenes or polyacenes are a class of organic compounds and polycyclic aromatic hydrocarbons made up of benzene () rings which have been linearly fused. They follow the general molecular formula . The larger representatives have potential interest in optoelectronic applications and are actively researched in chemistry and electrical engineering. Pentacene has been incorporated into organic field-effect transistors, reaching charge carrier mobilities as high as 5 cm2/Vs. The first 5 unsubstituted members are listed in the following table: Hexacene is not stable in air, and dimerises upon isolation. Heptacene (and larger acenes) is very reactive and has only been isolated in a matrix. However, bis(trialkylsilylethynylated) versions of heptacene have been isolated as crystalline solids. Larger acenes Due to their increased conjugation length the larger acenes are also studied. Theoretically, a number of reports are available on longer chains u ...
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