Английская Википедия:4-Nitrotoluene

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4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

Synthesis and reactions

Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene,[1] commonly using titanium(IV) nitrate.[2] 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. Depending on the conditions, oxidation yields 4-nitrobenzaldehyde diacetate,[3] 4-nitrobenzenoic acid,[4] and 4,4'-dinitrobibenzyl.[5] Treatment of 4-nitrotoluene with bromine gives the 4-nitrobenzyl bromide.[6]

Applications

The principal application involves its sulfonation to give the 4-nitrotoluene-2-sulfonic acid (with the –SO3H group adjacent to methyl). This species can be oxidatively coupled to produce stilbene derivatives,[7] which are used as dyes.[8] Representative derivatives include the molecular and salt forms of 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids, e.g. disodium 4,4'-dinitrostilbene-2,2'-disulfonate.[9]

Safety

Evidence exists for toxicity and carcinogenicity in mice.[10]

References

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External links