Dichlorotoluene
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Dichlorotoluene
Dichlorotoluenes are organochlorine compounds, in particular aryl chlorides, with the formula . Six constitutional isomers exist, differing in the relative position of the two chlorine substituents around the ring. They are all colorless and lipophilic. The 3,5 isomer is a solid at room temperature, whereas the others are liquids. Preparation and uses Several dichlorotoluenes are prepared by treatment of toluene or monochlorotoluenes with chlorine in the presence of various Lewis acids. Purification is challenging because the individual isomers have similar properties. The 2,6 and 3,5 isomers do not form acceptably from toluene or chlorotoluenes, so these isomers are prepared by indirect methods. For example, 2,6-dichlorotoluene can be prepared by chlorination of P-toluenesulfonyl chloride, 4-toluenesulfonyl chloride followed by desulfonation. Some dichlorotoluenes are precursors to commercial pesticides. 2,4-Dichlorotoluene is the precursor to pyrifenox, butafenacil, and the ...
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Dichlobenil
2,6-Dichlorobenzonitrile (DCBN or dichlobenil) is an organic compound with the chemical formula C6H3Cl2CN. It is a white solid soluble in organic solvents. It is widely used as a herbicide and organic chemistry building block.Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry 2010 Mechanism of action It has herbicidal properties killing young seedlings of both monocot and dicot species. DCBN interferes with cellulose synthesis. DCBN adapted cell walls use minimal amounts of cellulose, instead relying on Ca2+-bridge pectates. Dichlobenil kills the roots of many species, but not all; further, the killing does not extend much beyond the portion actually soaked, according to the Californian department of agriculture in 1971. Application In 1996, the University of California reported that "dosages were difficult to control... and as a result soaking or spraying methods are no longer used. ... The curren ...
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Chlorotoluene
Chlorotoluenes are aryl chlorides based on toluene in which at least one aromatic hydrogen atom is replaced with a chlorine atom. They have the general formula C7H8–''n''Cl''n'', where ''n'' = 1–5 is the number of chlorine atoms. Monochlorotoluene Monochlorotoluenes are chlorotoluenes containing one chlorine atom. There are three isomers, each with the formula C7H7Cl. Properties The isomers differ in the location of the chlorine, but have the same chemical formula. All have very similar boiling points, although ''p''-chlorotoluene has a much higher melting point due to a more tightly packed crystal structure. Benzyl chloride is an isomer, which has a chlorine substituted for one of the hydrogens of toluene's methyl group, and it is sometimes named α-chlorotoluene. Preparation A laboratory route to 2- and 4-chlorotoluene proceeds from 2- and 4-toluidines (i.e. 2- and 4-aminotoluene). These compounds are diazotization, diazotized followed by treatment with cuprous chlo ...
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Organochlorine Compounds
Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted by chlorine) includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious. Organochlorides such as trichloroethylene, tetrachloroethylene, dichloromethane and chloroform are commonly used as solvents and are referred to as "chlorinated solvents". Physical and chemical properties Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. They have higher b ...
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Toluenes
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent. As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant and has the potential of causing severe neurological harm. History The compound was first isolated in 1837 through a distillation of pine oil by Pierre Joseph Pelletier and Filip Neriusz Walter, who named it ''rétinnaphte''. In 1841, Henri Étienne Sainte-Claire Deville isolated a hydrocarbon from balsam of Tolu (an aro ...
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Trichlorotoluene
Trichlorotoluenes are organochlorine compounds, in particular aryl chlorides, with the formula . Six constitutional isomers exist, differing in the relative position of the three chlorine substituents around the ring. All isomers colorless and lipophilic solids. Preparation and use Four trichlorotoluenes—the 2,3,4-, 2,3,6-, 2,4,5-, and 2,4,6- isomers—are produced in significant yields by treatment of toluene with three equivalent (chemistry), equivalents of chlorine in the presence of various Lewis acids. These isomers result from the usual regioselectivity, selectivity of electrophilic aromatic substitution reactions of substituted benzenes. 2,3,6-Trichlorotoluene is a precursor to 2,3,6-trichlorobenzoic acid (2,3,6-TBA), a commercial herbicide. Related compounds * Dichlorotoluene References

{{Reflist Toluenes Chlorobenzene derivatives Multiple compounds, tabular ...
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