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Home > 4-Nitrotoluene > 4-Nitrotoluene for synthesis

N2 - It was shown that Ba(BrF4)2 acts like a highly-active brominating agent in case of interaction with p-nitrotoluene, the pure 3-bromo-nitrotoluene is formed. It was shown that typical electrophilic bromination of the aromatic compound with electron-donating and electron-accepting substituents occurs without any catalysts or hard conditions.

It was shown that Ba(BrF4)2 acts like a highly-active brominating agent in case of interaction with p-nitrotoluene, the pure 3-bromo-nitrotoluene is formed. It was shown that typical electrophilic bromination of the aromatic compound with electron-donating and electron-accepting substituents occurs without any catalysts or hard conditions.

4-Nitrotoluene for synthesis Supplier: MilliporeSigma: ..

p-nitrotoluene bromination using barium fluorobromate …

About alternative routes I'm afraid nothing is as simple as the oxidation of p-nitrotoluene.

AB - It was shown that Ba(BrF4)2 acts like a highly-active brominating agent in case of interaction with p-nitrotoluene, the pure 3-bromo-nitrotoluene is formed. It was shown that typical electrophilic bromination of the aromatic compound with electron-donating and electron-accepting substituents occurs without any catalysts or hard conditions.

On the other hand, deactivating substituents destabilize the intermediate cation and thus decrease the reaction rate. They do so by withdrawing electron density from the aromatic ring, though the positions most affected are again the ortho and para ones. This means that the most reactive positions (or, least unreactive) are the meta ones (atoms 3 and 5). Examples of deactivated aromatic rings are nitrobenzene, benzaldehyde and trifluoromethylbenzene. The deactivation of the aromatic system also means that generally harsher conditions are required to drive the reaction to completion. An example of this is the nitration of toluene during the production of trinitrotoluene (TNT). While the first nitration, on the activated toluene ring, can be done at room temperature and with dilute acid, the second one, on the deactivated nitrotoluene ring, already needs prolonged heating and more concentrated acid, and the third one, on very strongly deactivated dinitrotoluene, has to be done in boiling concentrated sulfuric acid.

Search results for p-nitrotoluene at Sigma-Aldrich

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2,6-DINITROTOLUENE | C7H6N2O4 - PubChem


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