100 PROCEEDINGS OF THE AMERICAN ACADEMY 



depositing crystals on cooling, which seem by their melting point to be 

 the unaltered substance ; strong hydrochloric acid seems to have no 

 action, whether hot or cold ; sodic hydrate seems not to act upon it. 



Action of other Reagents on TribrommononitrohenzoL 



Sodic methylate behaved in much the same way as the sodic ethyl- 

 ate, except that it was necessary in this case to heat for a longer 

 time, and even after this a certain amount of tribrommononitrobenzol 

 was apt to be left unaltered. The product after crystallization from 

 alcohol showed the constant melting point 104°, but its analyses gave 

 percentages of bromine differing from those corresponding to dibrom- 

 nitroanisol by about one per cent. The cause of this is probably the 

 same as that of the similar want of agreement between the calculated 

 and observed percentages in the case of the bromdinitroresorcine 

 dimethylether ; * but we have not thought the substance of sufficient 

 importance to try to obtain better analytical results, which, to judge 

 by our work on the bromdinitroresorcine dimethylether, would be a 

 matter of great difficulty. 



From these experiments it appears that the tribrommononitrobenzol 

 acts with sodic alcoholates less easily than the tribromdinitrobenzol, 

 which is attacked by them in the cold forming the ethers of bromdi- 

 nitroresorcine, whereas it is necessary to heat the mononitro com- 

 pound to bring about any action. When the tribromdinitrobenzol is 

 heated with an alcoholate, the third atom of bromine is replaced by 

 hydrogen and an ether of the dinitroresorcine is formed, but we found 

 no trace of any action of this sort with the mononitro compound. It 

 is to be noted, too, that only one atom of bromine is removed from 

 the mononitro, but two from the diuitro compound. 



The inertness of tribrommononitrobenzol as compared with the cor- 

 responding dinitro compound is made even more evident by the study 

 of the action of aniline upon it. This substance converts tribromdi- 

 nitrobenzol into trianilidodinitrobenzol, when heated with it for a short 

 time, whereas the corresponding trinitro compound is formed in the 

 cold ; from the mononitro substance we were unable to obtain any 

 anilido compound, even after heating for some time to the boiling 

 point of aniline ; a little aniline bromide was formed, it is true, but 

 almost all of the tribrommononitrobenzol was recovered unaltered, 

 as recognized by its melting point and very characteristic crystalline 

 form. 



* These Proceedings, XXV. 175. 



