80 PB0Ci3EDINGS OP THE AMERICAN ACADEMY 



acid, forming in the latter case a very loose spongy blackish mass. 

 It is soluble in alcohol with a yellowish brown color like that of ferric 

 chloride ; insoluble in ether, or benzol ; water decomposes the salt 

 almost completely, forming a yellow precipitate and a pale brotvn solu- 

 tion, which is strongly alkaline. The action of the anilidotrinitroto- 

 luol with alkaline reagents was also studied, and, as was to be expected, 

 no action was obtained with acid, or neutral carbonate of sodium, or 

 ammonic hydrate in aqueous solutions ; but if the action was assisted 

 by the presence of alcohol, each of these reagents gave a barely per- 

 ceptible reddish coloi'ation, so slight in the case of ammonic hydrate 

 that we were doubtful whether there had been any action ; sodic 

 hydrate in aqueous solution gave a slight yellow coloration, which, on 

 the addition of alcohol, was at once converted into a very dark blood- 

 red. The acid character of the anilidotrinitrotoluol therefore is much 

 less marked than that of the nitrite of anilidotrinitrophenylmalonic 

 ester, and as the position of the anilido group with regard to the nitre 

 groups is the same in both compounds, we must ascribe this to the 

 presence of the nitrite of the malonic ester radical CN02(COOC2H5)2, 

 with its large amount of oxygen in place of the indifferent methyl con- 

 tained in the toluol. 



Bromtrinitrophenyltartronic Ester, C6HBr(N02)3COH(COOC2H5)2. 



If the nitrite of bromtrinitrophenylmalonic ester, or the ester itself, 

 was heated for some time with nitric acid, it was converted into the 

 corresponding tartronic ester, which we found it convenient to prepare 

 as follows : — 1 gr. of bromtrinitrophenylmalonic ester was mixed 

 with about 10 c. c. of nitric acid of specific gravity 1.38, and heated on 

 the water bath for three hours in a dish covered with a watch-glass, 

 fresh nitric acid being added when necessary to replace that lost by 

 evaporation. At the end of this time the substance was found to be 

 completely dissolved in the small quantity of hot nitric acid left, but 

 upon cooling colorless crystals separated, which, after washing with 

 water, were essentially the pure substance, one recrystallization from 

 alcohol being all that was needed to make them melt at 156°, the con- 

 stant melting point of this compound. If, as was usually the case, the 

 bromtrinitrophenylmalonic ester was contaminated with acetylene- 

 tetracarbonic ester, a yellowish oil was also formed, which however 

 remained dissolved in the nitric acid mother liquor. The amount of 

 the substituted tartronic ester in this mother liquor was so small that 

 it did not pay for the working up. 



The bromtrinitrophenyltartronic ester can also be made from the 



