298 PROCEEDINGS OF THE AMERICAN ACADEMY 



With a cadmium salt, reddish yellow. 



With a lead salt, whitish red. 



With a silver salt, pale orange. 



Strong nitric acid gave with the salts a white precipitate, probably 

 the unaltered ester. In this respect it differs from bronitrinitro- 

 phenylmalonic ester. 



Bromanilidodinitrophenylmalonic Ester, 

 C 6 HBr(C 6 H 5 NH)(N0 2 ) 2 CH(COOC 2 H 5 ) 2 . 



This substance was made by adding aniline to the dibromdinitro- 

 phenylmalonic ester in the proportion of a little more than two mole- 

 cules of the base to one of the ester. The reaction began in the 

 cold, but was brought to an end by warming the mixture for a short 

 time on the water bath. The product, after washing with water, to 

 which a little hydrochloric acid was added to remove aniline bromide 

 and the excess of aniline, was crystallized from hot alcohol, until it 

 showed the constant melting point 127°, when it was dried at 100°> 

 and analyzed with the following result : — 



0.2003 gr. of the substance gave 14.85 c.c. of nitrogen at a tem- 

 perature of 20°. 5 and a pressure of 762 mm. 



Calculated for 

 C 6 HBr(C G H 5 XII)i X0 2 ) 2 CH(C0 2 C 2 H 5 ) 2 . Found. 



Nitrogen 8.47 8.49 



Properties. — The bromanilidodinitrophenylmalonic ester crystal- 

 lizes from alcohol in bright red needles, which under the microscope are 

 seen to be slender prisms terminated usually by two planes, less com- 

 monly by one, and seeming to belong to the monoclinic system. The 

 substance melts at 127° ; and is essentially insoluble in cold water, 

 very sparingly soluble in boiling water, as shown by the faint yellow 

 color imparted to the liquid ; insoluble in ligroine ; very slightly solu- 

 ble in cold ethyl or methyl alcohol, more freely in either of these 

 solvents when hot; slightly soluble in ether; soluble in benzol or 

 glacial acetic % acid; freely soluble in chloroform, carbonic disulphide, 

 or acetone. Strong sulphuric acid dissolves it slightly, forming a 

 yellowish solution ; the solubility did not seem to be increased by 

 heat. Strong nitric acid dissolved it rather more freely than sul- 

 phuric acid, and the solubility was increased by heat. Strong hydro- 

 chloric acid had no action upon it, although it is probable that long 

 heating in a sealed tube with this acid would have decomposed it in 

 the way described * under the bromdinitropbenylmalonic ester. 



* These Proceedings, xxiv. 240. 



