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270 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

nitroso structure is ascribed (Fischer and Hepp [5], Green and Crossland [6]).

They are easily oxidized by atmospheric oxygen to give nitro derivatives of

dibenzyl and stilbene:

(1)

On melting with anhydrous KOH the oxidation of the methyl group takes

place. with simultaneous reduction of the nitro group:

(2)

By treating a sulpho derivative of p- nitrotoluene with NaOCl the correspon-

ding nitrostilbenesulphonic acid is obtained:

(3)

This is a valuable intermediate in the manufacture of direct dyes.

The methyl group in nitrotoluene is activated by the nitro group and can react,

for example, with p- nitrosodimethylaniline to form an anil:

TOXICITY

Nitrotoluenes are considered to be toxic substances, though their toxicity is

considerably lower than that of nitrobenzene. It has been suggested that this should

be ascribed to the ease with which nitrotoluene is oxidized in the human body

to nitrobenzoic acid, which is only slightly toxic.