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A laboratory route to 2- and 4-chlorotoluene proceeds from 2- and 4-toluidines (i.e. 2- and 4-aminotoluene). These compounds are diazotized followed by treatment with cuprous chloride. [1] Industrially, the diazonium method is reserved for 3-chlorotoluene. The industrial route to 2- and 4-chlorotoluene entails direct reaction of toluene with ...
Using an acid ratio of 30/56/14, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene, with only about 1% 3-nitrochlorobenzene. Since the above synthetic route does not efficiently produce the 3-isomer, the route most commonly used by chemists is the chlorination of nitrobenzene .
4-Nitrochlorobenzene is the organic compound with the formula ClC 6 H 4 NO 2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including antioxidants commonly found in rubber. Other isomers with the formula ClC 6 H 4 NO 2 include 2-nitrochlorobenzene and 3 ...
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c 6 h 5 cl + hno 3 → o 2 nc 6 h 4 cl + h 2 o This reaction affords a mixture of isomers. Using an acid ratio of 30% nitric acid, 56% sulfuric acid and 14% water, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene , with only about 1% 3-nitrochlorobenzene .
Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene, [4] commonly using titanium(IV) nitrate. [5] It undergoes the reactions typical for nitrobenzene derivatives, e.g. hydrogenation gives p-toluidine. Oxidation of the methyl substituent of 4-nitrotoluene has been extensively investigated.
For example, the three isomers of xylene CH 3 C 6 H 4 CH 3, commonly the ortho-, meta-, and para-forms, are 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene. The cyclic structures can also be treated as functional groups themselves, in which case they take the prefix "cyclo alkyl -" (e.g. "cyclohexyl-") or for benzene, "phenyl-".
It is a colorless solid. A related isomer is 1,2,3,4-tetrachloro-5-nitrobenzene. It is used as a standard for quantitative analysis by nuclear magnetic resonance. [4] [5] 1,2,4,5-Tetrachloro-3-nitrobenzene is also a fungicide used to prevent dry rot and sprouting on potatoes during storage. [6] [7]