Meta-Nitrotoluene

The bromination of meta-nitrotoluene is an example for a high-temperature, high-pressure (high p,T) side-chain bromination of alkylaromatics [25]. 

However, methylating nitrobenzene leads to the formation of meta nitrotoluene because the nitro group is meta directed. 

Composition Mixture of about 62 per cent ortho-, 34 per cent para-, and 4 per cent meta-nitrotoluenes. 

By comparing the above summaries, it is seen that the ortho compound of the earlier chemists is identical with the present meta nitrotoluene, and vice versa. That the early view was incorrect may be further proved by investigating the properies of the meta compounds. In all reactions the meta compounds react differently from the ortho and para compounds. For instance, in the nitration of toluene, the ortho and para nitrotoluenes are formed in large amounts, and the meta in small amounts. Further, when the mono-nitrotoluenes are nitrated to dinitrotoluene, the ortho and para mononitrotoluenes are very easily nitrated further, and the meta difficultly so. In other words, the ortho and para compounds form one part of the class, while the meta stands alone as the other part. With the early nomenclature, the meta and para would be placed together, while the ortho would stand alone. If, now, this view of the matter is accepted. Von Richter s statement becomes entirely correct. 

Meta nitrotoluene crystallizes in monoclioic prisms, and para nitrotoluene crystals belong to the trunetric system. 

A considerable amount of para nitrotoluene may be separated from the above residue, and easily enough so that further methods of preparation would be superfluous. A very small amount of the meta nitrotoluene is present, also, but this amount is too small to be of... 

The side-chain bromination of meta-nitrotoluene was selected (Scheme 6.13) as this aromatic reacts very poorly without aid of light (even worse than toluene). 

The reactants were contacted in a high-pressure interdigital micromixer followed by a capillary reactor, all immersed in an oil bath [45,46]. Pure bromine and pure aromatic were fed, mixed and reacted. By a high-temperature, high-pressure (high-p,T) route, the side-chain bromination of meta-nitrotoluene was achieved. This allows one to extend the operational range much beyond the boiling point, which is the technical limit of many reactions carried out batchwise. 

SYNONYMS 3-methylnitrobenzene, m-methylnitrobenzene, mnt, 3-nitrotoluene, meta-nitrotoluene. 

Synonyms/Trade Names m-MethyInitrobenzene, 3-Methylnitrobenzene, meta-Nitrotoluene, 3-Nitrotoluene... 

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